MINISTRY OF HEALTH OF UKRAINE

NATIONAL UNIVERSITY OF PHARMACY

DEPARTMENT OF DRUG AND ANALYTICAL TOXICOLOGY

Collection of Multiple Choice Questions

on Toxicological Chemistry with answers and explanations

for self-training foreign students

in specialty 8.12020101 "Pharmacy"

Kharkiv

2017

UDC 54.01:615 (075)

Revieweres:

A. I. Panasenko, Professor, Doctor of Pharmacy; head of Toxicological and

Inorganic Chemistry Department, Zaporizhzhia State Medical

University;

I. S. Gritsenko, Professor, Doctor of Сhemistry; head of Analytical Chemistry

Department, National University of Pharmacy;

L. A. Toryanik, Assistant professor of Foreign Language Department, PhD in

Pedagogical Science; National University of Pharmacy.

Karpushyna S.A.

Collection of Multiple Choice Questions on Toxicological Chemistry with

answers and explanations : for self-training foreign students in specialty 8.12020101

"Pharmacy". – Kh.: NUPh Publishing, 2017. – 92 p.

This сollection of multiple choice questions on Toxicological Chemistry with

answers and explanations is intended for individual work of foreign English-course-

language students in specialty 8.12020101 Pharmacy. The collection of MCQ

includes the following topics: Introduction into Toxicological Chemistry;

Regularities of the poison behaviour in a body and metabolism; Metallic poisons;

Volatile poisons; Pesticides; Drugs; Mineral acids, alkalis, nitrate and nitrite; Carbon

monoxide. The theoretical and practical aspects of toxicokinetics, sample preparation,

toxicological screening, identification and quantitative determination of poisonous

substances are displayed. The manual teaching is recommended for Pharmaceutical

faculties and Pharmaceutical universities of III-IV accreditation levels.

3

CONTENTS

INTRODUCTION

4

TOPIC: INTRODUCTION INTO TOXICOLOGICAL CHEMISTRY.

GENERAL RULES OF POISON BEHAVIOUR IN A BODY

5

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE

BIOLOGICAL MATERIAL BY MINERALIZATION (METALLIC

POISONS)

9

TOPIC: GROUP OF SUBSTNCES ISOLATED FROM THE

BIOLOGICAL MATERIA BY STEAM DISTILLATION (VOLATILE

POISONS)

27

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE

BIOLOGICAL MATERIA BY ORGANIC SOLVENT EXTRACTION

(PESTICIDES)

41

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE

BIOLOGICAL MATERIAL BY SOLVENT EXTRACTION (DRUGS)

50

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE

BIOLOGICAL MATERIAL BY EXTRACTION WITH WATER

77 TOPIC: SUBSTANCES DETERMINED IN THE BIOLOGICAL

MATERIAL WITHOUT ISOLATION (CARBON MONOXIDE)

82 TABLES FOR SELF-CONTROL OF ANSWERS TO MCQ

(REFERENCE REPLIES)

84 LITERATURE

88

4

INTRODUCTION

This сollection of multiple choice questions on Toxicological Chemistry with

answers and explanations is intended for individual work of foreign English-course-

language students in specialty 8.12020101 Pharmacy. The collection of MCQ

includes the questions on the following topics: Introduction into Toxicological

Chemistry; Regularities of the poison behaviour in a body and metabolism; Metallic

poisons; Volatile poisons; Pesticides; Drugs; Mineral acids, alkalis, nitrate and nitrite;

Carbon monoxide. The theoretical and practical aspects of toxicokinetics, sample

preparation, toxicological screening, identification and quantitative determination of

poisonous substances are displayed.

The correct answers are given at the end of the manual. There are short

comments and explanations as Nota bene for the tests relating to the key issues of the

topic, or for the most difficult questions. This manual will help the student to self-

prepare for the current and the final module control.

The manual teaching is recommended for Pharmaceutical faculties and

Pharmaceutical universities of III-IV accreditation levels.

5

THEMATIC MODULE 1. Introduction into toxicological chemistry. Basic laws

of poisonous substance behaviour in an organism. Groups of substances, isolated

from the biological material by water extraction, mineralization, steam

distillation

TOPIC: INTRODUCTION INTO TOXICOLOGICAL CHEMISTRY. GENERAL

RULES OF POISON BEHAVIOUR IN A BODY

Organization and rules of chemicotoxicological analysis performing

1. Professional activity of forensic toxicologist, the duties and rights are

regulated by the Criminal Procedure Code. Forensic toxicologist has the right:

A. To refuse the difficult toxicological examination

B. To carry out the interrogations

C. Do not give the expert conclusion for the difficult questions

D. To review the case materials concerned with the toxicological examination

E. To give the expert conclusion on the basis of one reaction or one analytical

method in the case of lack of reagents or instruments

2. The indirect forensic-toxicological research of corpse is carried out.

What group of poisons is the analysis started with?

A. Metallic poisons

B. Volatile poisons

C. Medicinal poisons

D. Pesticides

E. Mineral acids, alkalis and inorganic salts

3. Preservation of the samples for forensic-toxicological examination is

forbidden to use any substance. However, as the exception, the preservation is

assumed with the help of:

A. Formaline

B. Ethyl alcohol

C. Phenol

D. Chloramine

E. Methyl alcohol

4. Storage or transportation of the samples for forensic-toxicological

6

examination supposes their preservation. In this case the delivery of the ethanol

sample used for preservation is:

A. Performed at the requirement of investigation and court

B. Not necessarily together with the sample of the examination

C. Performed at the special query of the expert performing the analysis

D. Performed at the query of the forensic-medical expert

E. Necessary together with the sample of the examination

Preliminary tests in chemicotoxicological analysis

5. When examining corpse material for the presence of ammonia it is

necessary to take into account the probability of ammonia formation as a

product of the biological material decomposition. Therefore, before ammonia

detection the biological sample is tested for the presence of:

A. Nitrogen (ІІ) oxide

B. Carbon sulphide

C. Carbon (IV) oxide

D. Carbon (II) oxide

E. Hydrogen sulphide

6. At the forensic-toxicological examination different reagent papers can

be used. The litmus paper and paper treated with copper sulphate turned dark-

blue. What substance can be suspected:

A. Hydrogen sulphide

B. Hydrogen chloride

C. Ammonium hydroxide

D. Sulphuric acid

E. Sodium hydrochloride

7. At the forensic-toxicological examination different reagent papers can

be used. The reagent paper treated with lead acetate is turned in black. It

indicates the presence in the biological sample:

A. Hydrogen chloride

B. Hydrogen sulphide

C. Sulphuric acid

D. Sodium hydroxide

E. Ammonium hydroxide

7

8. For the preliminary decision of the question about the cause of

poisoning the determination of biological material pH is carried out with the

help of indicator paper scraps. Paper scrap moistened by lead acetate alkaline

solution is turned in black under the action of fumes of the biological material

examined. This testifies to the presence in the biological material of:

A. Methane

B. Ammonia

C. Hydrogen sulphide

D. Carbon monoxide

E. Carbon dioxide 9. Forensic-toxicological examination of the biological sample for the

presence of alkalis is carried out. First pH value and the presence of an alkali

metal carbonate should be determined. The following reagents are added to the

obtained biological extract for this purpose:

A. Barium chloride solution and phenolphthalein ethanol solution

B. Barium sulphate solution and phenolphthalein aqueous solution

C. Barium carbonate solution and phenolphthalein ethanol solution

D. Strontium sulphate solution and phenolphthalein ethanol solution

E. Barium sulphate solution and methyl orange aqueous solution

Metabolism of xenobiotics

10. O-methylation is an important pathway of xenobiotic

biotransformation in an organism. Substances undergo this route of

biotransformation if they contain the following functional group:

A. Nitro group

B. Amino group

С. Thiol group

D. Phenolic group

E. Carboxyl group 11. Biotransformation of xenobiotics in an organism occurs in two phases.

What metabolic transformation is referred to the Phase II reactions?

A. Oxidation

B. Conjugation

C. Reduction

D. Hydrolysis

E. Dealkylation

8

12. Biotransformation of xenobiotics in an organism occurs in two phases.

The processes referred to the second phase of metabolism decrease:

A. Toxicity of xenobiotics

B. Solubility of toxic substances in water

C. Polarity of toxic substances

D. Speed of toxic substance excretion

E. Speed of organism detoxication

13. Xenobiotics undergo the biotransformation and become:

A. Less polar

B. Polarity is not changed

C. More volatile

D. Less soluble in water

E. More polar 14. In an organism toxic substances are exposed to destruction by

biotransformation. The main mechanism of ester biotransformation is:

A. Reduction

B. Desulphonation

C. Hydrolysis

D. Oxidation

E. Hydroxylation

15. Which substance metabolizes with forming hippuric acid?

A. Glucuronic acid

B. Glutathione

C. Glycine

D. With sulphates

E. With glutamine

Detoxification

16. At decontamination of poisonous substances by kidneys it is necessary

to take into account the urine pH. Acidic xenobiotics are excreted more quickly

by kidneys at:

A. Urine pH does not affect

B. Acidic urine

C. Neutral urine

D. Alkaline urine

E. Urine pH affects slightly

9

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIAL BY MINERALIZATION (METALLIC POISONS)

Toxicity and antidotes in metal compound poisonings

1. What is the toxicological value of arsenic compounds based on? On

their application in:

A. Pyrotechnics

B. Food industry

C. Light industry

D. Medicine

E. Manufacture of fusible alloys

2. Poisoning by a metallic poison happened. What is the reason of toxic

action of metallic poisons?

A. Binding with lipids

B. Binding with amino acids, proteins and polypeptides

C. Binding with carbohydrates

D. Binding with hydrochloric acid

E. Binding with cholesterol

3. Barium salt was taken by mistake. What barium salt is not toxic for a

living organism?

А. Barium nitrate

B. Barium carbonate

C. Barium sulphate

D. Barium acetate

E. Barium chloride

4. Mercury (II) chloride and ethyl mercuric chloride are highly toxic

substances. Ethyl mercuric chloride is more toxic than mercury (II) chloride

because of the presence in its structure of:

A. Ethyl radical

B. Mercury (ІІ) cation

C. Chloride ion

D. Carbon atoms

E. Ionic bond

10

5. Mercury compounds are toxic substances. The toxicity rate of

compounds depends on their chemical structure. What substance is the most

toxic?

A. Hg2Cl2

B. C2H5HgCl

C. HgCl2

D. HgO

E. Hg2O

6. When performing toxicological examination dark blue-green stomach

content was observed. Which substance should the toxicological examination be

carried out for?

A. Ammonium oxalate

B. Barium chloride

C. Potassium nitrate

D. Sodium chloride

E. Copper sulphate

7. In the case of heavy metal or arsenic compound poisoning the following

antidote is used:

A. Glucagon

B. Vitamin B6

C. Lipoic acid

D. Methyl blue

E. Unithiol

8. What medicine as antidote must be present for the first aid at an

industrial enterprise where acute poisoning by arsenic, mercury, chromium or

bismuth compounds is possible?

A. Adrenalin

B. Unithiol

C. Atropine

D. Droperidol

E. Morphine 9. At barium salt poisoning such specific chemical antidote is used:

A. Potassium iodide

B. Sodium chloride

11

C. Sodium sulphate

D. Sodium carbonate

E. Copper acetate 10. What specific antidote is used at poisoning by iron preparations?

A. Penicillamine

B. Bemegride

C. Atropine sulphate

D. Deferoxamine

E. Protamine sulphate

11. The toxic substances are divided into groups according to the isolation

method from the biological material. What method is used for isolation of the

metallic poisons:

A. Infusion with acidified ethanol or acidified water

B. Steam distillation

C. Mineralization of the biological material

D. Infusion with water

E. Infusion with lipophilic solvent

12. Mineralization is the isolation method of the metallic poisons from the

biological material. Mineralization of the biological samples when heating in the

crucible to high temperature at free air is named:

A. Distillation

B. Alloying

C. Wet ashing

D. Extraction

E. Dry ashing 13. At research of the biological material for the presence of a metallic

poison the mineralization by the mixture of nitric and sulphuric acids is carried

out. The first stage of the mineralization is:

A. Oxidization

B. Denitration

C. Sulphurization and nitration

D. Ashing

E. Destruction

12

14. When performing the mineralization by the mixture of sulphuric and

nitric acids the end of this process is determined by:

A. Yellow colour of liquid in the reaction flask

B. Orange colour of liquid in the reaction flask

C. The absence of black inclusions at heating to heavy white steam liberation

and when nitric acid addition is discontinued

D. The absence of colour changes of liquid when nitric acid is added

E. After expiration of the set time

15. Which scientist was the first to suggest the idea of the necessity of the

mineralization in the study of the biological material for the presence of heavy

metal compounds?

A. Nelyubin A. P.

B. Ravdanikis P. K.

C. Krilova A. N.

D. Zaykovskiy F. V.

E. Shvaykova M. D.

16. What oxidizers are used for the mineralization destruction of the

biological material by the Kaan method?

A. Hydrogen peroxide and sulphuric acid

B. Nitric acid

C. Sulphuric and nitric acids

D. Sulphuric, nitric and perchloric acids

E. Hydrogen peroxide and hydrochloric acid NB! Inorganic mercury compounds are isolated from the biological material by the

special method which is called destruction because mercury and its compounds are

volatile 17. The biological sample contains mercury. What method is used for

isolation of mercury compounds from the biological material?

A. Mineralization

B. Destruction

C. Steam distillation

D. Extraction with organic solvent

E. Extraction with acidified ethanol

13

18. Various poisons are isolated from the biological material using

different methods. Inorganic mercury compounds are isolated from the

biological material by the following method:

A. Infusion with ethanol acidified by oxalic acid

B. Mineralization

C. Steam distillation

D. Infusion with by water acidified by sulphuric acid

E. Destruction

19. Which metallic poison is isolated from the biological material by the

mineralization destruction?

A. Silver

B. Mercury

C. Thallium

D. Cadmium

E. Antimony

20. Using the mineralization destruction for isolation of mercury

compounds from the biological material allows:

A. To mask the interfering cations

B. To decrease the duration of the biological material destruction

C. To warn the severe losses of mercury compounds in the conditions of the

hard thermal mode

D. To increase the method sensitivity for mercury detection in the biological

material

E. To decrease the method sensitivity for mercury detection in the biological

material 21. Some metallic poison is separated from the biological material by the

destruction method. What metallic poison is separated by this method?

A. Antimony

B. Mercury

C. Cadmium

D. Silver

E. Arsenic

14

22. For the prevention of mercury loss during forensic-toxicological study

of the biological material some special isolation method is used. This method is

named:

A. Destruction

B. Denaturation

C. Degradation

D. Disintegration

E. Mineralization NB! Denitration is the process of removing nitric, nitrogenous, nitrososulphuric acids

and nitrogen oxides from the mineralizate. These substances are oxidizers, which

prevent the analysis for metallic poisons. Denitration is performed by adding to the

mineralizate various reductants. The most effective reductant is formalin.

23. After the metallic poisons isolation using mineralization the denitration

is carried out. What method of the denitration is the most widespread and fast?

A. Distillation

B. Hydrolysis

C. By urea

D. By sodium sulphate

E. By formalin 24. For denitration of the mineralizate different reductants can be used.

What reagent is the most effective for denitration?

A. Sodium sulphate

B. Thiourea

C. Formaldehyde solution

D. Urea

E. Sodium thiosulphate

25. For the mineralizate denitration different reductants were proposed.

What reagent is used for denitration?

A. Thiourea

B. Solution of formaldehyde

C. Sodium sulphite

D. Urea

E. Sodium of thiosulphate

15

26. Poisoning by inorganic mercury compounds happened. After

destruction of the biological sample the denitration is carried out with the help of:

A. Urea

B. Formalin

C. Sodium sulphate

D. Sodium thiosulphate

E. Sodium sulphide

27. After the biological material mineralization the denitration is carried

out. Which reagent is used for verification of the denitration completeness?

A. Diphenylamine

B. Urea

C. Diphenyldithiocarbazone

D. Diethyldithiocarbamate

E. Glycerol 28. Forensic toxicologists examines the mineralizate obtained from the

biological material. For verification of the denitration completeness the

following reagent is used:

A. Aniline solution

B. Diphenylbenzidine solution

C. Diphenylamine in concentrated sulphuric acid

D. Dithizone solution

E. α-Naphthol solution 29. Which scientist suggested the method of the mineralizate denitration

using formaldehyde?

A. Krylova A. N.

B. Nelyubin A. P.

C. Kramarenko V. F.

D. Zaykovskiy F. V.

E. Shvaykova M. D.

Detection and identification of metallic poisons in the mineralizate

NB! In the chemical toxicological analysis of metallic poisons the fractional method

is used. The fractional method is based on using the reactions, which allow to detect

metallic cations in separate small portions of the solution examined. Tananaev N. A.

was the founder of the fractional analysis method.

16

30. Which scientist was the founder of the fractional analysis method?

A. Tananaev N. А.

B. Krylova A. N.

C. Kaan

D. Sherbak A.

E. Nelyubin A. P. NB! Masking the interference ions is one of the main approaches used in the

fractional method. Complexation, the binding the interference ions into colourless

stable complexes, is widely used for this purpose. Cyanide, fluoride, phosphate are

used for masking many trace metals.

31. In the fractional analysis method masking is one of the main methods

of eliminating the interference ion influence. The basic masking method is:

A. Oxidation

B. Evaporation

C. Complexation

D. Extraction

E. Destruction 32. To mask which cation when detecting cobalt cation in the mineralizate

by the reaction with ammonium rhodanide according to the fractional analysis

method is fluoride used?

A. Copper (II) cation

B. Ferric (III) cation

C. Cadmium cation

D. Lead cation

E. Bismuth cation

33. To mask which cation when studying the mineralizate in accordance

with the fractional analysis method is phosphate used?

A. Zinc (II)

B. Copper (II)

C. Iron (III)

D. Cadmium (II)

E. Manganese (II)

17

34. To mask which cation when studying the mineralizate in accordance

with the fractional analysis method is phosphate used?

A. Cuprum (II)

B. Zinc (II)

C. Plumbum (II)

D. Cadmium (II)

E. Ferrum (III)

35. For masking the interference ions in the fractional method of the

metallic poisons analysis various reagents are used. Usage of fluoride for this

purpose is based on its ability to form colourless stable complexes with the

following cation:

A. Mg2+

B. Fe2+

C. Ba2+

D. Fe3+

E. Ag+ 36. In chemicotoxicological analysis of heavy metal compounds the masking

copper (II) cations when performing the fractional method following reagent is used:

A. Fluoride

B. Glycerol

C. Thiourea

D. Cyanide

E. Phosphate

37. In the fractional analysis method various chelating agents are used for

elimination of the interference ions. Follow-up destruction of the complexes

obtained is named:

A. Masking

B. Dismasking

C. Denitration

D. Mineralization

E. Extraction NB! Separation of PbSO4 and BaSO4 .To separate barium and lead sulphates obtained

after minaralization the precipitate is washed by a hot solution of ammonium acetate

which results in dissolving PbSO4.

18

38. The mineralizate studied contains sediments of barium sulphate and

lead sulphate. These salts may be separated with the use of:

A. Acetic acid

B. Sulphuric acid

C. Ammonium acetate solution

D. Sodium acetate solution

E. Ammonium nitrate solution

39. The mineralizate contained white precipitate of lead sulphate, barium

sulphate and strontium sulphate. What procedure should be used to separate

lead sulphate?

A. Transformation into arsine

B. Dissolution in concentrated sulphuric acid

C. Transformation into carbonate

D. Transformation into diethyldithiocarbamate

E. Dissolution in ammonium acetate

NB! Dithizone is often used as a reagent in the qualitative analysis of metallic poisons

Dithizonates can be coloured. Dithizonates are dissolved in organic solvents and

destroyed by acids, and this fact is used for separating some heavy metal cations from

the mineralizate.

40. Some complexation reactions are used as preliminary tests. Which

reaction is used for detection of thallium cations in the mineralizate?

A. With thiourea

B. Sodium rhodizonate

C. With dithizone

D. With diphenylcarbazide

E. With sulphuric acid 41. It is necessary to detect and determine mercury ions in the

mineralizate. Which reaction is used for this purpose?

A. With sodium rhodizonate

B. With dithizone

C. With diphenylcarbazide

D. With thiourea

E. With ammonium persulphate

19

42. Metal poisoning happened. During the reaction with dithizone

chloroform layer is turned in pink. Which metallic poisons is it necessary to

carry out the confirmative reactions for?

A. Manganese and chromium

B. Thallium and antimony

C. Copper and bismuth

D. Lead and zinc

E. Silver and arsenic

43. Poisoning by heavy metals happened. Which metal detection is the

preliminary test with dithizone used for?

A. Copper and cadmium

B. Zinc and silver

C. Arsenic and antimony

D. Manganese and chromium

E. Bismuth and copper

44. At the mineralizate study for the presence of zinc the following

reaction is used as the preliminary test:

A. With dithizone

B. With diphenylcarbazide

C. With sodium rhodanide

D. With thiourea

E.With diethyldithiocarbamate

45. Heavy metal poisoning happened. The reaction with dithizone is

carried out when studying the mineralizate. Which heavy metal does not react

with this reagent:

A. Thallium

B. Silver

C. Mercury

D. Lead

E. Barium 46. What is dithizone by the chemical structure?

A. Diphenylcarbazone

B. Diphenyldithiocarbazone

20

C. Diphenylthiocarbazone

D. Dithiocarbazone

E. Dithiophenylcarbazone

Detection of Lead compounds

47. For the metallic poison isolation from the biological material the

mineralization by the mixture of sulphuric and nitric acids was carried out. In

the process the white precipitate was obtained. It testifies to the possible

presence of:

A. Lead

B. Thallium

C. Zinc

D. Copper

E. Antimony

48. What metallic poison is detected with KI by the reaction of “gold rain

formation”?

A. Mn2+

B. Cu2+

C. Pb2+

D. Ag+

E. Ba2+

Detection of Barium compounds

49. For the mineralization of the biological material the mixture of nitric

and sulphuric acids is used. What metal cation forms insoluble sulphate:

A. Copper

B. Barium

C. Silver

D. Manganese

E. Zinc

50. When studying the mineralizate for the presence of barium cations the

reaction with sodium rhodizonate is used. What colour is the product of this

reaction?

A. Red

B. Yellow

21

C. Brown

D. Violet

E. Dark blue

51. What is barium rhodizonate in appearance?

A. Prismatic crystals

B. Red solution

C. Yellow solution

D. Blue-violet sediment

E. Red-brown sediment

Detection of Manganese compounds NB! For detection of Manganese compounds the reactions of Mn2+ oxidization by

means of potassium periodate or ammonium persulphate to permanganate-ion are

carried out.

52. The preliminary test of the mineralizate for the presence of manganese

compounds is carried out. What reagent is used?

A. Thiourea

B. Potassium periodate

C. Copper acetate

D. Sulphuric acid

E. Dithizone

53. A man was poisoned by manganese salt. The manganese (II) cations

are detected in the mineralizate. What reactions are in the base of chemical

method of manganese detection?

A. Dissociation reactions

B. Hydrolysis reaction;

C. Oxidation-reduction

D. Neutralization reactions

E. Exchange reactions

54. When carrying out the reaction with potassium periodate a violet

colour is appeared. It testifies the presence in the mineralizate the following

metallic poison:

A. Zinc

B. Manganese

22

C. Cadmium

D. Arsenic

E. Antimony

Detection of Chromium compounds

55. What reaction is used for detection of chromium (III) cations?

A. With malachite green

B. With dithizone

C. With sodium rhodizonate

D. With diphenylcarbazide

E. With thiourea

Detection of Copper compounds NB!. The reaction with (DDTC)2Pb is preliminary for Cu2+. The yellow-brown colour

of the chloroform layer is observed. With the positive result of this reaction a copper

cation is re-extracted into the aqueous layer by HgCl2 and confirmative reactions are

carried out (e.g. the reaction with ammonium mercuric thiocyanate).

56. In the fractional analysis method in order to eliminate the interference

ion influence the copper (II) cation is separated from the mineralizate using the

reagent:

A. Ammonium tetrarhodanomercuriate

B. Dithizone

C. Lead diethyldithiocarbamate

D. Potassium hexacyanoferrate

E. Sodium sulphate

57. When study the mineralizate copper was detected. What reagent was

used for preliminary detection of the copper (II) cations in the mineralizate?

A. Dithizone

B. Sodium DDTC

C. Lead DDTC

D. Diphenylcarbazide

E. Diphenylamine

23

58. What reaction is used for detection of the copper (II) cations in the

mineralizate?

A. With thiourea

B. With dithizone

C. With ammonium persulphate

D. With ammonium mercuric thiocyanate

E. With 8-oxyiquinoline

Detection of Bismuth compounds NB! The reactions with 8-oxyquinoline and thiourea are carried out. Both reactions

are preliminary. With the positive result of these reactions Bi3+ is separated from the

mineralizate as (DDTC)3Bi, then re-extracted by nitric acid and the re-extract is used

for the confirmative research – the reaction with thiourea is performed again.

59. It is necessary to prove the presence of bismuth (III) cation in the

mineralizate. Which preliminary reaction is used for this purpose?

A. With dithizone

B. With copper acetate

C. With potassium chromate

D. With 8-oxyquinoline

E. With sodium rhodizonate 60. Bismuth poisoning results in severe damage of kidneys. Which

preliminary reaction is used for detection of bismuth in the mineralizate?

A. With thiourea

B. With brucine and potassium bromide

C. With calcium chloride and potassium iodide

D. With copper acetate

E. With dithizone

61. Which reaction for bismuth (III) cation detection in the mineralizate is

used both preliminary and confirmative?

A. With 8-oxyquinoline

B. With thiourea

C. With calcium chloride and potassium iodide

D. With brucine and potassium bromide

E. With sodium diethyldithiocarbamate

24

Detection of Zinc compounds

62. When detecting the zinc (II) cation in the mineralizate some ions can

interfere with the analysis. So zinc is separated from the mineralizate by its

conversion into:

A. Hexacyanoferroate (ІІ)

B. Dithizonate

C. Diethyldithiocarbamate

D. Sulphide

E. Tetrarhodonomercuroate

Detection of Antimony compounds

63. The mineralizate is studied for the presence of antimony. For this

purpose following reaction is used:

A. With lead sulphate and ammonium mercuric thiocyanate

B. With malachite green

C. With diphenylcarbozide

D. With dithizone

E. With sodium rhodizonate

Detection of Arsenic compounds

NB! The Sanger-Bleck test is preliminary. The Marsh test is one of the most specific

tests for arsenic detection in the mineralizate. The sample to be tested is mixed with

the Zn(s) and H2(SO4)(aq).The resulting AsH3(g) passes through a tube that is divided

into two sections by a narrow constriction that is strongly heated with an alcohol lamp

or gas burner. AsH3(g) thermally decomposes and the As(s) deposits as a mirror thin

coating in the second section of the Marsh tube. Antimony, if present in the sample,

will also deposit as a metallic mirror during the Marsh test and testing the mirror with

the aqueous solution of chlorinated lime or calcium hypochlorite [Ca(OCl)2] is

necessary to distinguish these two deposits.

64. The mineralizate is studied for the presence of arsenic compounds. The

analysis is started with:

A. Reactions with (DDTC)Ag in pyridine

B. Sanger-Bleck Test

C. March’s method

25

D. Reaction with dithizone

E. Reaction with thiourea

65. In the chemicotoxicological analysis of metallic poisons the March’s

reaction is used. Which metallic poisons can be detected by this reaction?

A. Barium and manganese

B. Arsenic and cadmium

C. Tin and antimony

D. Arsenic and antimony

E. Bismuth and lead

66. Which reaction of arsenic compound detection in the biological

material is specific:

A. Reaction with sodium diethyldithiocarbamate

B. Zanger-Blek’s reaction

C. Reaction with of silver diethyldithiocarbamate pyridine solution

D. Reaction with dithizone

E. March’s reaction

67. When carrying out the March test for the presence of arsenic in the

mineralizate the mirror thin coating in the Marsh tube should be tested to

except presence in the sample following metallic poison:

A. Zinc

B. Silver

C. Thallium

D. Cadmium

E. Antimony 68. Formation of thin coating in the March tube is one of the most

essential proofs of arsenic presence in the mineralizate studied. However, it is

necessary to take into account, that the thin coating may be due to following

metallic poison deposits:

A. Cadmium

B. Barium

C. Antimony

D. Bismuth

E. Zinc

26

Quantitative analysis of metallic poisons

NB! Mercury dithizonate is coloured, and this fact is used in quantitative

determination of this metallic poison by extraction-photometric method.

69. In chemicotoxicological analysis for quantitative determination of

mercury compounds in the biological material the extraction-photometric

method can be used. It is based on the reaction with:

A. Sodium thiosulphate

B. Sodium sulphide

C. Diphenylcarbazide

D. Dithizone

E. Thiourea

70. Toxicologist used the extraction-photometric method for quantitative

determination of mercury in the sample. What reagent was used for mercury

determination by this method?

A. Dithizone

B. Sodium thiosulphate

C. Sodium sulphide

D. 8-oxyquinoline

E. Thiourea

For notes:

27

TOPIC: GROUP OF SUBSTNCES ISOLATED FROM THE BIOLOGICAL

MATERIA BY STEAM DISTILLATION (VOLATILE POISONS)

Metabolism of Volatile poisons

1. Hydrocyanic acid and its salts are the extraordinarily toxic substances.

In an organism cyanide toxicity decreases due to the enzymatic

biotransformation to:

A. Carbon (IV) oxide

B. Thiocyanate

C. Nitrogen (ІІ) oxide

D. Ethanol

E. Acetic acid

2. During toxic substance metabolism formaldehyde can appear in an

organism. In this case the reason of intoxication is:

A. Isopropyl alcohol

B. Ethanol

C. Resorcinol

D. Methanol

E. Acetone

3. Formaldehyde was detected in the distillate. What substance is the

reason of intoxication?

A. Aminazine

B. Chloral hydrate

C. Methanol

D. Chlorodiazepoxide

E. Chloroform

4. Methanol is widely used in industry. Negligible amount of this alcohol

administrated an organism results in heavy disorders of human health. This

effect is explained by action of the main methanol metabolite:

A. Acetic acid and acetic aldehyde

B. Ethyl alcohol and acetic aldehyde

C. Methyl acetate and ethyl acetate

D. Ethyl alcohol and ethyl acetate

E. Formaldehyde and formic acid

28

5. In methanol poisoning the blindness occurs. It is related to metabolism

of this substance in an organism and formation of such toxic metabolite as:

A. Formaldehyde

B. Methanol conjugate

C. Carbon (II) oxide

D. Carbon dioxide

E. Formic acid

6. Substances administrated an organism are exposed to enzymatic

biotransformation. What is the main pathway of polyatomic alcohol

metabolism?

A. Reduction

B. Hydroxylation

C. Dealkylation

D. Oxidation

E. Conjugation

NB! Strong odour produced by the sample for toxicological study assumes the

presence of Volatile poisons

7. Organs of dead body have an odour of bitter almond. What volatile

poison presence is it necessary to carry out the toxicological study for?

A. Phenol

B. Hydrocyanic acid

C. Acetone

D. Acetic acid

E. Chloroform 8. Samples of liver, kidney, stomach with the content are delivered to

forensic-toxicological laboratory. Stomach was ulcerated, stomach content

contains the bloody admixtures with specific odour. What substance is it

necessary to carry out toxicological study for:

A. Copper sulphate

B. Acetic acid

C. Chlorophos

D. Formaldehyde

E. Novocaine

29

9. Poisoning by a volatile poison happened. Urine has a dark green colour.

What volatile poison can be suspected as the reason of the poisoning?

A. Formaldehyde

B. Methanol

C. Phenol

D. Acetone

E. Ethanol

10. In the medical practice this substance is used for disinfection. In

poisoning by this substance the urine is turned in olive or black olive. Which

substance is it?

A. Acetoethyl ether

B. Isoamyl alcohol

C. Iodoform

D. Phenol

E. Ethylbenzoate

11. The urine sample was sent to forensic-toxicological laboratory. Phenol

poisoning is suspected. Which external sign indicates the phenol poisoning:

A. Olive colour urine

B. Colourless urine

C. Light orange urine

D. Sulphide smell produced by urine

E. Acetone smell produced by urine NB! The antidotes are used in acute intoxications by cyanide and ethylene glycol.

12. In treatment of cyanide poisoning a range of antidotes are used. What

antidote contributes to the formation of methaemoglobin?

A. Ethanol

B. Atropine

C. Sodium hydrocarbonate

D. Unithiol

E. Methylene blue

13. In poisoning by antifreeze contained ethylene glycol the following

substance is used as biochemical antidote:

A. Unithiol

30

B. Nalorphine

C. Ethanol

D. Atropine

E. Amylnitrite NB! Steam distillation is the main isolation method of Volatile poisons.

14. When isolating substances related to the group of volatile poisons the

protein-volatile poison bond is broken. What method is used for this purpose:

A. Extraction

B. Infusion with alcohol

C. Mineralization

D. Steam distillation

E. Dialysis

15. Dead body organs are sent for toxicological study. Chloral hydrate

poisoning is suspected. What method is used to isolate this poison?

A. Extraction by organic solvent

B. Infusion with acidified alcohol

C. Infusion with acidified water

D. Mineralization

E. Steam distillation

16. The following substance is isolated by steam distillation:

A. Barbituric acid

B. Sodium nitrite

C. Phenol

D. Quinine

E. Carbon (IV) oxide NB! Steam distillation of some Volatile poisons has the characteristic features

17. Cyanide poisoning happened. The isolation is carried out by the

method of steam distillation. The vessel for collection of the distillate must

contain:

A. Solution of iodine

B. Solution of sodium hydroxide

C. Solution of sulphate acid

31

D. Solution of sodium chloride

E. Solution of chloride acid

18. Forensic-toxicological study of stomach content for the presence of

volatile poisons is carried out. Thus, the first fractions of the distillate are

collected into receiver containg:

A. Sodium hydroxide solution

B. Sulphuric acid solution

C.Hydrochloric acid solution

D. Oxalic acid solution

E. Chloroform

19. Forensic-toxicological examination for volatile poisons is carried out.

When isolating by steam distillation method methanol is collected in:

A. Vessel with distillated water

B. Empty vessel

C. Vessel with sodium hydroxide

D. Cooled vessel

E. Vessel with hydrochloric acid

20. Isolation of particular volatile poisons has the characteristic features.

When isolating phenol from the biological sample it is necessary to perform:

A. Collection of the distillate in cooled vessel

B. Collection of the distillate in sodium hydroxide solution

C. Concentration of the poison by extraction with diethyl ether

D. Collection of the distillate in empty vessel

E. Collection of the distillate in sulphuric acid solution

21. Isolation of particular volatile poisons has the characteristic features.

When isolating isopentanol from the biological sample it is necessary to

perform:

A. Collection of the distillate in empty vessel

B. Collection of the distillate in sodium hydroxide solution

C. Collection of the distillate in chilled vessel

D. Concentration of the poison by extraction with diethyl ether

E. Collection of the distillate in sulphuric acid solution

32

22. Isolation of particular volatile poisons has the characteristic features.

When isolating acetic acid from the biological sample it is necessary to perform:

A. Concentration of the poison by extraction with diethyl ether

B. Collection of the distillate in sodium hydroxide solution

C. Collection of the distillate in chilled vessel

D. Collection of the distillate in empty vessel

E. Collection of the distillate in sulphuric acid solution

23. Directed forensic-toxicological study for the presence of acetic acid is

carried out. What acid is used for acidification of the biological sample for steam

distillation?

A. Formic acid

B. Sulphuric acid

C. Hydrochloric acid

D. Oxalic acid

E. Nitric acid 24. When isolating poisonous volatile substances from the biological

material by steam distillation method formic and oxalic acids are used. Mineral

acids, phosphoric or sulphuric, are used when isolating:

A. Chloral hydrate

B. 1,2-dichloroethane

C. Acetone

D. Ethanol

E. Acetic acid 25. Ethylene glycol is isolated from the biological material by the steam

distillation method. In this a method the selective transporter of ethylene glycol is:

A. Benzene

B. Ethyl alcohol

C. Heptane

D. Toluene

E. Chloroform

26. Ethylene glycol isolation method by Lapkina-Nazarenko technique is

effective to separate the alcohol from the biological material. What selective

transporter of ethylene glycol is used in this method?

A. Chloroform

33

B. Water

C. Benzene

D. Ethyl alcohol

E. Acetone NB! The vapour phase method uses the transfer of the volatile poison examined to

the vapour phase followed by the analysis of the resulting phase with the help of the

gas chromatography (GC) method.

27. Express testing the urine and blood for the presence of alcohols is

carried out. Which method is used:

A. Liquid chromatography

B. Dialysis

C. Electrophoresis

D. Vapor phase analysis

E. Hydrolysis

Analysis of Volatile poisons by chemical method

28. Poisoning by formaldehyde happened. What identification reaction for

formaldehyde does not prove the presence of formaldehyde in the distillate if a

blue-violet colour of the solution appears in 30 minutes after the beginning of this

reaction?

A. Reaction with codeine in sulphuric acid solution

B. Reaction with chromotropic acid

C. Reaction with fuchsinsulphuric acid

D. Reaction with resorcinol in alkaline solution

E. Reaction with Fehling’s reagent

29. What reaction for formaldehyde detection is based on the formation of

copper oxide and dihydroxide sediment?

A. Reaction with chromotropic acid

B. Reaction with Fehling’s reagent

C. Reaction with fuchsinsulphuric acid

D. Reaction with methyl violet

E. Reaction with codeine and sulphuric acid

34

30. Poisoning by some volatile poison happened. When performing the

reaction with resorcinol in alkaline solution the pink colour is observed. What

volatile poison doesn’t give this reaction?

A. Tetrachloromethane

B. Chloroform

C. Chloral hydrate

D. Formaldehyde

E. Acetone

31. Toxicologist carries out testing the distillate for the presence of volatile

poisons. What reagent is used for detection of acetone in the distillate?

A. Bromine water

B. Furfural

C. The Millon’s reagent

D. Lanthanum nitrate

E. Fuchsinsulphuric acid

32. What reaction is not used for acetone detection in the distillate in the

practice of toxicological analysis:

A. Formation of indigo

B. Formation of iodoform

C. Formation of izonitrile

D. With furfural

E. With sodium nitroprusside

33. Acetic acid can be detected in the distillate by the reaction:

A. Formations of izonitrile

B. With Fehling’s reagent

C. With resorcinol

D. With ferric (III) chloride

E. With benzaldehyde

34. What reaction or method is the most evidential for the detection of

hydrocyanic acid in the distillates after steam distillation?

A. Microdiffusion

B. Ferric rhodanide formation

C. Benzidine blue formation

35

D. Reaction with ferric (III) chloride

E. Prussian blue formation

35. When detecting ethylene glycol by its oxidization to oxalic acid the

following reagent is used:

A. Nitric acid

B. Potassium iodate

C. Sodium nitrite

D. Potassium iodate

E. Ferric chloride 36. What substance can interfere with the ethylene glycol detection by the

chemical method?

A. Hydrocyanic acid

B. Acetone

C. Chloroform

D. Methanol

E. Phenol

37. Distillate is studied for the presence of volatile substances. The reaction

with salicylic acid, the oxidization reaction with potassium permanganate or

dichromate followed by adding chromotropic or fuchsinsulphuric acid were

positive. The most credible poisonous substance is:

A. Methyl alcohol

B. Ethylene glycol

C. Formaldehyde

D. Ethyl alcohol

E. Chloral hydrate

38. Some volatile poison was detected in the second distillate. What

substance interferes with the detection of methanol in the distillate by the

chemical method?

A. Acetone

B. Formaldehyde

C. Ethanol

D. Chloral hydrate

E. Izopentanol

36

Detection of phenol

39. Forensic-toxicological study of the distillate for the presence of volatile

poisons is carried out. The reaction with ferric (III) chloride resulted in the blue-

violet colour. Which volatile poison can be suspected?

A. Ethanol

B. Acetic acid

C. Phenol

D. Acetone

E. Aniline

40. Preliminary testing the distillate for the presence of phenol was

positive. Which reagent can confirm its presence in the distillate:

A. Marqui’s reagent

B. Millon’s reagent

C. Froehde’s reagent

D. Fehling’s reagent

E. Nessler’s reagent 41. Which reaction for phenol detection is based on the formation of

indophenol?

A. Reaction with benzaldehyde

B. Reaction with bromine water

C. Reaction with ferric (III) chloride

D. Reaction with the Millon’s reagent

E. Libermann reaction

42. The Libermann reaction which is used for phenol detection is based on

the formation of:

A. Indigo

B. Tribromophenol

C. 1,2-Quinon monoxime

D. Indophenol

E. Iodophorm NB! Ethanol and acetone give the reaction of iodoform formation.

37

43. Which substance interferes with the iodoform test when detecting ethyl

alcohol in the biological material?

A. Acetone

B. Isoamyl alcohol

C. Formaldehyde

D. Phenol

E. Methanol 44. When distillate testing the iodoform test resulted in specific odour.

This test is positive for:

A. Chloroform

B. Methanol

C. Ethanol

D. Dichloroethane

E. Izoamyl alcohol

45. Poisoning by acetone happened. The iodoform test was positive when

examining the distillate. Which substance can interfere with the detection of

acetone:

A. Phenol

B. Formaldehyde

C. Ethyl alcohol

D. Chloral hydrate

E. Cresol

Detection of Halocarbons

46. What reaction is used for the preliminary detection of chlorinated

hydrocarbons?

A. Formation of copper acetylide

B. With Fujiwara reagent

C. With quinoline

D. With silver nitrate

E. Formation of formaldehyde

47. The reaction of chlorine separation is used for detection of:

A. Acetone

B. Ethyl alcohol

38

C. Phenol

D. Chloroform

E. Formaldehyde 48. Chloral hydrate, a sedative and hypnotic drug, in overdose can cause

poisoning. Its detection by the reaction with the Nessler’s reagent can be

mistaken in the case of the presence in the biological material of:

A. Dichloroetane

B. Chloroform

C. Tetrachlorometane

D. Aldehydes

E. Chlorinated ethylene

The reactions distinguishing chlorinated halocarbons from each other

49. Chlorinated hydrocarbon intoxication happened. Which reaction

allows to distinguish chloroform from tetrachloromethane?

A. With Fehling’s reagent

B. Isonitrile formation

C. With resorcinol alkaline solution

D. Fujiwara reaction

E. Separation of organically bound chlorine

50. Poisoning by 1,2-dichloroethane happened. What reaction allows to

distinguish it from other chlorinated halocarbons?

A. Fujiwara reaction

B. Reaction of ethylene glycol formation followed by its oxidation to formaldehyde

C. Reaction of izonitrile formation

D. Reaction of chlorine separation

E. Reaction with alcohol solution of silver nitrate

51. What reaction can be used for distinguishing chloral hydrate from

chloroform?

A. Separation of organically bound chlorine

B. With Fehling’s reagent

C. Fujiwara reaction

D. With resorcinol alkaline solution

E. With Nessler’s reagent

39

NB! Gas-Liquid chromatography uses a gas as a mobile phase and a liquid coated on

a support material as an immobile phase. The retention time is defined as the time

from injection of the substance into chromatograph to the peak maximum at the

detector.

52. Gas-liquid chromatography is widely used for identification and

quantitative determination of toxic substances. Substances can be injected into

the chromatographic column in the following aggregate states:

A. Gaseous and solid

B. Liquid and solid

C. Liquid

D. Liquid and gaseous

E. Gaseous

53. In Gas Liquid Chromatography the separation of mixture components

takes place between immobile liquid phase and mobile phase (carrier-gas). Thus,

the separation of complex mixture is produced by:

A. Chemical reaction between a mixture component and carrier-gas

B. Adsorption and desorption of a mixture component on the support material

C. Adsorption and desorption of a mixture component on the immobile liquid

phase

D. Chemical reaction between a mixture component and the immobile liquid

phase

E. Solubility of mixture components in the immobile liquid phase

54. The method of Gas Liquid chromatography is used for identification of

toxic substances. The identification of substances with the Gas Liquid

chromatography method is carried out by:

A. Area of peak

B. Retention parameters

C. Character of zero line

D. Height of peak

E. Width of peak on the half of its height

55. Ethanol poisoning happened. Detection and identification of ethanol by

GLC is carried out by:

A. Absolute height of the peak

40

B. Relative height of the peak

C. Retention time

D. Area of the peak

E. Width of the peak base 56. Poisoning by alcohols happened. What derivatives of alcohols are used

in the analysis by GLC method?

A. Alkylnitrites

B. Alkylnitrates

C. Alkylsulphites

D. Alkylsulphates

E. Alkylacetates

57. Poisoning happened. When detecting the toxic substance by Gas

Liquid Chromatography method the detector which determined heat

conductivity was used. The technical name of this detector is:

A. Electron-capture

B. Flame-ionization

C. Thermionic

D. Katharometer

E. Helium

For notes:

41

THEMATIC MODULE 2. Group of substances, isolated from the biological

material by extraction (pesticides, drugs). Substances isolated by special

methods and determined directly in the biological samples without isolation.

Analytical diagnosis of acute intoxications, drug addiction and substance abuse

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIA BY ORGANIC SOLVENT EXTRACTION (PESTICIDES)

Usage, toxicity of pesticides, antidotes in pesticide poisonings

1. To destroy large areas of forests and agricultural crops US first used in

the war against Vietnam the “agent orange” pesticide which caused falling

leaves. This pesticide refers to a group of:

A. Acaricides

B. Desikants

C. Defoliants

D. Repellentes

E. Fungicides NB! Natural and synthetic pyrethrins are derivatives of cyclopropancarboxylic acids,

the esters. The natural pyrethrin insecticides are esters of keto-alcohols – cinerolone,

jasmolone, pyrethrolone and chrysanthemum or pyrethrin acids. The basic structure

of natural pyrethrin insecticides:

CH3

CH3

R 1

CH3

O

O O

R 2

CH3

2. Synthetic pyrethrins by the chemical structure are:

A. Heterocycle compounds

B. Esters

C. Amides

D. Phenols

E. Aldehydes NB! The main route of heptachlor metabolism is oxidation to heptachlor epoxide

which is more toxic than the parent substance.

42

Cl

Cl

Cl

Cl Cl

CCl2

Cl

Cl

Cl

Cl Cl

CCl2

O[O]

heptachlor epoxide of heptachlor

3. Some poisonous substances are converted in living organisms to more

toxic products. Because of heptachlor oxidation the following more toxic

substance appears:

A. Hexachlorocyclohexane

B. Carbon monoxide

C. Carbon dioxide

D. Heptachlor oxide

E. Heptachlor epoxide NB! Chlorinated pesticides, e.g. heptachlor, accumulate in a human organism,

forming body depot for pesticides storage (the material accumulation), mainly in the

adipose tissue.

4. Pesticide poisoning happened. Which pesticide has got the material

accumulation?

A. Carbaryl

B. Chlorophos

C. Metaphos

D. Heptachlor

E. Permethrin NB! Organophosphorus compounds are the cholinesterase inhibitors. Cholinesterase

is the catalyst of acetylcholine hydrolysis leading to choline and acetic acid

formation:

[CH3COOCH2CH2N(CH3)3]+OH-

cholinesterase

H2OCH3COOH + [HOCH2CH2N(CH3)3]

+OH-

The organophosphorus pesticide poisoning is accompanied by accumulation of

acetylcholine, the transmitter of nervous impulses. Atropine as a pharmacological

antagonist to the organophosphorus compounds and cholinesterase reactivators: 2-

PAM (pralidoxime), dipyroxime and isonitrozine, are administered as specific

antidotes.

43

5. Some antidote was given to the victim with the organophosphorus

pesticide intoxication. Which antidote is an organophosphorus compound

pharmacological antagonist?

A. Atropine

B. Methylene blue

C. Caffeine

D. Unithiol

E. Ethanol

6. Blocking the cholinesterase by organophosphorus pesticides proceeds in

two stages. In the second stage cholinesterase phosphorylation, the chemical

interaction of PhOS with the enzyme, occurs. So in the case of

organophosphorus pesticide intoxication the antidote therapy is performed

using acetylcholinesterase reactivator:

A. Levomicetine

B. Dipyroxime and isonitrozine

C. Amylnitrate and sodium nitrite

D. Nalorfine

E. Dubinol

7. Granosan is one of the most toxic and dangerous pesticides. Its active

component is:

A. Carbaryl

B. Metaphos

C. Heptachlor

D. Hexachlorocyclohexane

E. Ethylmercury chloride

Isolation of pesticides

NB! The general isolation method of pesticides from the biological samples is

organic solvent extraction (hexane, ether, chloroform). Pesticides are volatile

(chlorinated pesticides, for example hexachlorocyclohexane, organophosphorus

pesticides, e.g. chlorophos (trichlorfon)) so they can be isolated by steam distillation.

8. Methods of pesticide isolation from the biological material are

determined by their physicochemical properties. What isolation method is the

general for organophosphorus pesticides:

A. Extraction by water

44

B. Extraction by water acidified with oxalic acid

C. Extraction by organic solvents

D. Extraction by alcohol acidified with oxalic acid

E. Extraction by acetonitrile acidified with hydrochloric acid 9. Poisonous substances are separated from the biological samples using

various methods. In organophosphorus pesticide poisoning the following

isolation method is used:

A. Infusion with organic solvents

B. Steam distillation from alkaline medium

C. Infusion with alkalified water

D. Infusion with water acidified by perchloric acid

E. Dialysis from alkaline solutions

10. In carbophos poisoning the acute depression of the acetylcholinesterase

activity resulted in conduct disorder and CNS dysfunction occurs. The isolation

of this pesticide from the biological material is carried out by:

A. Extraction by water acidified with oxalic acid

B. Extraction by chloroform

C. Steam distillation

D. Extraction with water

E. Mineralization

11. Biological sample is delivered for the forensic-medical examination.

The presence of trichlorfon and dichlorvos pesticides is suspected in the sample.

When isolating the poisons toxicologist will perform the infusion with:

A. Ethanol acidified by oxalic acid

B. Water alkalified by ammonia solution

C. Propanol acidified by oxalic acid

D. Chloroform

E. Water acidified by sulphuric acid 12. Methods of pesticide isolation from the biological material are

determined by their physicochemical properties. What isolation method is

specific for chlorophos (trichlorfon):

A. Mineralization by the mixture of concentrated sulphuric and nitric acids

B. Steam distillation

45

C. Destruction

D. Extraction by alcohol acidified with oxalic acid

E. Extraction by acetonitrile acidified with hydrochloric acid

13. Poisoning by hexachlorocyclohexane happened. Hexachlorocyclohexane

can be isolated from the biological material by the following method:

A. Extraction by a polar solvent

B. Extraction by water

C. Mineralization

D. Isolation is not necessary

E. Steam distillation NB! Trichlorfon (chlorophos) dissolves in water so it can be isolated from the

biological samples by extraction by water acidified with sulphuric acid.

14. Methods of pesticide isolation from the biological material are

determined by their physicochemical properties. What isolation method is

specific for chlorophos (trichlorfon):

A. Destruction

B. Mineralization by the mixture of concentrated sulphuric and nitric acids

C. Extraction by water acidified with sulphuric acid

D. Extraction by alcohol acidified with oxalic acid

E. Extraction by acetonitrile acidified with hydrochloric acid NB! For purification of pesticide extracts the following methods are most commonly

used: extraction, chromatography, combination of extraction and chromatography,

freezing-out of fat. Chromatography methods of purification include adsorption

column chromatography, paper chromatography, chromatography in a thin layer of

sorbent (TLC). TLC is the most widely applied because it provides the most careful

purification from admixtures.

15. In chemicotoxicological analysis of pesticides various purification

methods are used. What method provides the most careful purification from the

biological admixtures:

A. Centrifugation

B. Filtration

C. Thin layer chromatography

D. Extraction method

E. Freezing of fats

46

Detection and identification of pesticides

NB! The biochemical test (inhibition of cholinesterase test) is used for determination

of organophosphorus pesticides. The biochemical test is highly sensitive but non-

specific for organophosphorus pesticides. Inhibition of cholinesterase takes place

when taking carbamates, in such diseases as cirrhosis of the liver, anaemia, etc. The

analysis for organophosphorus compounds should be started with the biochemical

test because of its high sensitivity.

16. In biochemical laboratory the inhibition of cholinesterase test is

carried out. Which substance causes the inhibition of cholinesterase?

A. Heptachlor

B. Chloroform

C. Ethylmercury chloride

D. Trichlorfon (Clorophos)

E. Hexachlorane

17. When treating agricultural plant woman was poisoned. What reaction

is preliminary for PhOS pesticide detection in the extracts from the biological

samples?

A. The Biochemical test

B. The reaction for the phosphate-ion

C. The reaction for methoxy- or ethoxy-groups

D. The reaction for the presence of chlorine atom

E. The reaction for the presence of sulphur atom

18. Poisoning by pesticides happened. What reaction is preliminary for

PhOS pesticide detection in the extracts from the biological samples?

A. By methoxy- and ethoxy- groups

B. By sulphur

C. By phosphorus after mineralization

D. By chlorine

E. Biochemical test

19. Poisoning by organophosphorus pesticides happened. What method of

the analysis is used as a preliminary test for PhOS?

A. TLC

B. Biochemical test

47

C. Spectrophotometry

D. Chemical method

E. GLC 20. Biological sample is delivered to toxicological laboratory. PhOS

poisoning is suspected. The examination for this group of poisonous substances

is started with:

A. Reaction for sulphide anion

B. Reaction for phosphate anion

C. Biochemical test

D. Reaction for sulphate anion

E. Reaction for hydrocarbon chain

21. Teenager is delivered to hospital with suspicion of trichlorfon

(chlorophos) poisoning. The most sensitive method of this substance

detemination is:

A. Determination by phosphate anion

B. Determination of the active functional groups produced by hydrolysis

C. Cholinesterase test

D. Reaction for methyl group

E. Determination of phosphorylic ability

22. Poisoning by pesticides is found. The biochemical test gave the positive

result. What pesticide presence can be suspected?

A. DDT

B. Dichlorvos (Dichlophos)

C. Hexachlorocyclohexane

D. Heptachlor

E. Ethylmercury chloride

23. The detection of phosphorus is carried out by the reaction:

A. With sodium of nitroprusside

B. With ammonium molybdate

C. With silver nitrate

D. With zirconium salts

E. Prussian blue formation

48

24. Pesticide poisoning happened. Which pesticides are detected by azo

coupling reaction?

A. Carbophos

B. Carbaryl

C. Heptachlor

D. Chlorophos

E. Hexachlorocyclohexane

Quantitative analysis of pesticides

25. In chemicotoxicological analysis of pesticides various methods of

quantitative determination are used. What method is the most sensitive for

quantitative analysis of trichlorfon (chlorophos):

A. Argentometric

B. Photometric

C. Biochemical

D. Planimetric

E. Gravimetric

26. In chemicotoxicological analysis of pesticides various methods of

quantitative determination are used. What spot parameter is used when

determining chlorophos by thin layer chromatography in accordance with the

planimetric method:

A. Area of the colour spot on chromatogram

B. Colour intensity of the spot on chromatogram

C. Rf value of the spot on chromatogram

D. Rs value of the spot on chromatogram

E. Distance from the more faithful point of the spot to the line of start on

chromatogram

27. Quantitative determination of pesticides in the biological extracts is

carried out by various methods. What parameter is used when determining

chlorophos by thin layer chromatography in accordance with the densitometric

method:

A. Distance from the more faithful point of the spot to the line of start on

chromatogram

B. Area of the colour spot on chromatogram

49

C. Rf value of the spot on chromatogram

D. Rs value of the spot on chromatogram

E. Colour intensity of the spot on chromatogram

28. Quantitative determination of pesticides in the biological extracts is

carried out by various methods. What method of quantitative analysis of

chlorophos is based on the measurement of peak height:

A. Gas liquid chromatography

B. Thin layer chromatography

C. Photometry

D. Argentometry

E. Biochemical method NB! The product of of metaphos alkaline hydrolysis is p-nitrophenolate.

CH3O

PO

CH3O S

NO2

NaO NO2

NaOH

metaphos

29. Poisoning by a plenty of metaphos happened. Toxicologist uses the

photocolorimetric method for the quantitative determination of the poison. This

method is based on the reaction of metaphos alkaline hydrolysis resulting to the

formation of the following substance:

A. Thiophos

B. Nitrobenzene

C. Methanol

D. p-Nitrophenolate

E. Dimethylphosphanic acid

For notes:

50

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIAL BY SOLVENT EXTRACTION (DRUGS)

General and special methods of drug isolation from the biological material NB! Drugs are isolation from the biological material by infusion (extraction) with

acidified water or acidified ethanol (these extragents can be named the polar

solvents). In the indirected toxicological studies of the biological material for the

presence of drugs the general isolation methods are used. They are the extraction by

water acidified with oxalic acid (by Vasileva’s method) and the extraction by ethanol

acidified with oxalic acid (by Stas-Otto method).

1. Choose the isolation method of salicylates from the biological material:

A. Mineralization

B. Infusion with water

C. Extraction by acidified alcohol or acidified water

D. Steam distillation

E. Extraction by organic solvents

2. Choose the isolation method of phenacetin from the biological material:

A. Steam distillation

B. Infusion with water

C. Extraction by organic solvents

E. Extraction by acidified alcohol or acidified water

D. Mineralization

3. The following method is used to isolate ephedrine from the biological

material:

A. Extraction by a polar solvent

B. Extraction by a nonpolar solvent

C. Drug detection in the biological material without preliminary sample

preparation

D. Extraction by water

E. Extraction by an organic solvent 4. The various groups of poisons are isolated from the biological samples

using particular methods. The following method is used to isolate pyrazolones:

A. Extraction by water alkalified with sodium hydroxide

51

B. Extraction by water acidified with oxalic acid

C. Extraction by water

D. Mineralization by the mixture of sulphuric and nitric acids

E. Steam distillation

5. The following extragent is used to isolate a drug from the biological

sample by the Vasileva’s method:

A. Acidified water

B. Acidified ethanol

C. Acidified acetone

D. Acidified acetonitrile

E. Neutral acetonitrile

6. For isolation of drugs from the biological material various solvents are

used. Alcohol acidified by oxalic acid is used for the drug isolation by the following

method:

A. Vasileva’s method

B. Stas-Otto method

C. Valov’s method

D. Kramarenko’s method

E. Stepanov’s method

7. Isolation of a drug by the Stass-Otto method is carried out. In this

method the protein admixtures are precipitated with:

A. Acetone

B. Trichloroacetic acid

C. Ammonia chloride

D. Absolute ethanol

E. Acetonitrile

8. During drug isolation from the biological material by the Vasileva’s

method the most complete destruction of protein-poison bonds takes place at рН

values of:

A. 2-3

B. 4-5

C. 6-7

D. 9-10

E. 11-12

52

9. Isolation of alkaloids from the biological material with water acidified

by sulphuric acid in accordance with the Kramarenko’s method is carried out at

the рН values of 2-3 because:

A. Complete mineralization of the biological material takes place

B. Adsorption of alkaloids on a filter decreases

C. Destruction of protein-alkaloid complexes takes place

D. The need for filtering the extract disappears

E. The need for extracting alkaloids by chloroform disappears NB! The stages of the general isolation methods of drugs from the biological material

are infusion of the biological sample with acidified water or acidified ethanol;

purification of the extract from the biological admixtures; extraction of drug by an

organic solvent from acidic and then alkaline aqueous (or ethanol-aqueous) solutions.

In the general isolation methods chloroform is used as an organic solvent. Thus the

extracts obtained are labeled as “the acid chloroform extract” (acid, neutral, weak

basic drugs are detected here) and “the basic chloroform extract” (basic drugs are

detected here). But pyrazolones, weak basic drugs, could be detected both in the acid

chloroform extract and in the basic chloroform extract. There is the special isolation

method for these drugs. In this method the acidic aqueous extract obtained after

infusion of the biological sample is alkalified to pH values of 9-10 and pyrazolones

are extracted by chloroform.

10. In the directed toxicological study of the biological material for the

presence of pyrazolones the drugs are extracted by an organic solvent at the

following aqueous medium:

A. Neutral

B. Acidified to рН values of 1-2

C. Acidified to рН values of 4-5

D. Alkalified to рH values of 9-10

E. Alkalified to рH values of 12-13

Special methods of the drug isolation from the biological material NB! In directed toxicological studies of the biological material for the presence of a

particular drug or group of drugs the special isolation methods are used.

53

11. For drug isolation from the biological material various methods named

by the scientist names have been developed. In which method listed below the

water acidified with sulphuric acid is used as an extragent of drugs from the

biological sample?

A. Izotov’s method

B. Vasileva’s method

C. Stas-Otto method

D. Valov’s method

E. Kramarenko’s method

12. When isolating drugs by Kramarenko’s method ammonia sulphate is

added to purify the extract. What process or physical phenomena is in the base

of this purification method?

A. Extraction

B. Centrifugation

C. Filtration

D. Salting-out

E. Straining

13. When isolating drugs from the biological material protein admixtures

are extracted simultaneously with the substance determined. The effective

method of the extract purification from the protein admixtures is:

A. Salting-out

B. Filtration

C. Precipitation of admixtures at increased temperature

D. In-salting

E. Extraction 14. Which procedure is not used in the alkaloid isolation method by

Kramarenko?

A. Filtration

B. Infusion

C. Centrifugation

D. Extraction by ether

E. Extraction by chloroform

15. When isolating alkaloids from the decomposed biological material by

Kramarenko’s method crystalline ammonium sulphate is used. For what purpose?

A. To change of the extract рН

54

B. To create optimal ionic strength of the solution

C. To increase of specific density of the extract

D. To facilitate the sulphate conjugation

E. To precipitate the protein admixtures

16. Drug isolation by the Vasileva’s method is carried out. Which drug is

extracted by chloroform from acidic aqueous medium:

A. Codeine

B. Ephedrine

C. Benzonal

D. Aminazine

E. Atropine

17. Which chemical transformation of 1,4-benzodiasepines occurs when

isolating them from the biological material by the Izotov’s method?

A. Oxidation

B. Reduction

C. Hydrolysis

D. Esterification

E. Hydroxylation

18. The general isolation method of alkaloids from the biological material

is extraction by a polar solvent. Which alkaloid can be isolated by the steam

distillation?

A. Cocaine

B. Coniine

C. Strychnine

D. Atropine

E. Quinine

19. Bases of pyridine and piperidine alkaloids are volatile. To avoid their

losses when isolating them from the biological material these bases are

transformed into their non-volatile salts. Thus the chloroform extract containing

anabasine is saturated with:

A. Hydrochloride

B. Hydrogen sulphide

C. Carbon (IV) oxide

55

D. Ammonia

E. Carbon (II) oxide

20. Isolation of barbiturate by the Popova’s method is carried out. In this

isolation method the biological admixtures are removed using the following

purification method:

A. TLC

B. Centrifugation

C. Sublimation

D. Dialysis

E. Gel-chromatography

Methods used for chemicotoxicological analysis of drugs 21. Back extraction is the purification method based on the of liquid-liquid

extraction process. Liquid-liquid extraction is a substance separation method

which is based on the:

A. Different distribution of the components to be separated between two liquid

phases

B. Substance diffusion from the distribution surface between two liquid phases

into the extragent volume

C. Differences in the concentration of the components to be separated in two

liquid phases

D. Chemical interaction of the components to be separated with liquid phases

E. Substance adsorption on the surface of one phase 22. How is the substance transition from an organic solvent phase into

aqueous phase called?

A. Liquid extraction

B. Re-extraction

C. Washing away

D. Straining

E. Salting-out NB! Thin-layer chromatography (TLC) is a method widely used in toxicological

studies. In this method a mobile phase moves by capillary action across a uniform

thin layer of a finely divided stationary phase (adsorbent) bonded to a plate. The basic

chromatographic measurement of a substance in TLC is the Rf value, determined as:

56

Rf = The distance the solventtravels from the origin

The distance the substancetravels from the origin

23. TLC drug screening is carried out. The Rf value does not depend on:

A. Size of a chromatographic plate

B. Properties of substances being separated

C. Saturation of a chromatography chamber with mobile phase vapour

D. Composition of a mobile phase

E. Homogeneity of a sorbent layer NB! Immunoassays now occupy a sound place among routine methods for the

analysis of drugs in the biological fluids. The immunoassay technique uses an

antibody specific for the drug being assayed (antiserum), and a labelled form of the

same drug (labelled antigen). According to the kind of label (specific radioisotope, an

active enzyme, or fluorescent label incorporated synthetically) there are such kinds of

immunoassays: radioimmunoassay, enzyme immunoassay, fluoroimmunoassay.

When the bound and free labelled-drug are separated before measurement the assays

are referred to as heterogeneous immunoassays. The specific binding antibodies and

antigens takes place on the polystyrol plate with holes. Thus, no separation step and

the methods are referred to as homogeneous immunoassays. In homogeneous

immunoassays all components of the reaction (antibodies (antiserum), antigens

conjugated to the enzyme label, antigens that are the substance being determined, a

chromogenic substrate) are in the solution.

24. Opiate immunoassay is carried out with the urine on the polystyrol

plate using horseradish peroxidase as a chromogenic substrate. This method is

classified as:

A. Homogeneous enzyme immunoassay

B. Heterogeneous enzyme immunoassay

C. Fluoroimmunoassay

D. Heterogeneous fluoroimmunoassay

E. Heterogeneous radioimmunoassay

57

Chemicotoxicological analysis of the acid chloroform extract for presence of

acidic, neutral and weak basic drugs

Chemicotoxicological analysis of barbiturates NB! The preliminary colour test for barbiturates is the reaction with a cobalt salt in

alkaline medium. In the reaction with cobalt acetate in presence of lithium hydroxide

a blue colour appears. In the reaction with cobalt chloride in presence of potassium or

barium hydroxide a pink colour appears. In the reaction with cobalt acetate in

presence of ammonium hydroxide or isopropyl amine a violet colour appears. The

structure of the inner-complex compound that formed as a result of this reaction:

NH

N

O

O

O

C2H

5

C2H

5 Co NH

N

O

O

O

C2H

5

C2H

5

CH3

NH3

NH3

25. Which reaction is preliminary when detecting barbiturates in the urine

during toxicological studies?

A. With cobalt acetate and lithium hydroxide

B. With chlorine-zinc-iodine reagent

C. With ferric chloride-potassium iodide solution

D. With potassium diiodine cuproate

E. With potassium iodide acidic ethanol solution

26. Which reaction of the barbiturate detection results in a violet colour

appearance?

A. Reaction with a cobalt salt and alkali

B. Reaction with Rhodamine G

C. Reaction with chlorine-zinc-iodine reagent

D. Reaction with copper-pyridine reagent

E. Reaction with cobalt salts and isopropyl amine NB! Barbiturates give the crystalline precipitates with the following reagents: chlorine-

zinc-iodine reagent, ferric-iodine reagent, copper-iodine reagent, copper-pyridine

reagent.

58

27. Corps liver is sent to a toxicological laboratory for pathomorphological

diagnostics of barbiturate poisoning. Which reagent for barbiturates do not give

precipitation with?

A. Solution of cobalt nitrate in methanol

B. Chlorine-zinc-iodine reagent

C. Copper-pyridine reagent

D. Ferric-iodine reagent

E. Copper-iodine reagent NB! Majority of barbiturates give the Murexide reaction which resulting in a pink

colour. This reaction is unspecific (e. g., Caffeine, the purine, gives this reaction) and

little sensitive for barbiturates. Some barbiturates as Hexenalum and Cyclobarbital

don’t give the Murexide Test.

28. Toxicologist carried out the Murexide reaction which resulted in

forming a pink colour. Which drug could be suspected in the sample studied?

A. Atropine

B. Morphine

C. Strychnine

D. Barbamyl

E. Cocaine

29. The Murexide Test was positive during toxicological testing the urine.

Which group of drugs could be suspected?

A. Benzodiazepines

B. Phenothiazines

C. Barbiturates

D. Derivatives of indole

E. Salycilates

30. The Murexide Test is the general identification reaction for

barbiturates. The substances listed below give this reaction except for:

A. Caffeine

B. Barbamil

C. Barbital

D. Phenobarbital

E. Hexenalum

59

NB! Mercury sulphate spraying followed by the diphenylcarbazone chloroform

solution spraying is used for barbiturate visualisation in TLC drug screening (blue

and red-violet spots).

31. TLC drug screening is the preliminary test in indirected toxicological

studies. The detection of barbiturates is carried out by use:

A. Mercury sulphate then diphenylcarbazone in chloroform

B. Diphenylamine

C. Sodium diethyl dithiocarbamate

D. Dragendorff’s spray

E. Iodine vapour 32. For detection of barbiturates on the chromatogram the following

reagent (reagents) is (are) used:

A. Diphenylamine

B. Dragendorff’s reagent and then sulphuric acid

C. Solution of diphenylcarbazone

D. Iron (III) chloride

E. Mercury (II) sulphate and then diphenylcarbazone solution

Chemicotoxicological analysis of purine alkaloids NB! Purine alkaloids, Caffeine, Theobromine, Theophylline are weak basic

substances. When isolating by the general isolation methods purine alkaloids are

extracted by chloroform from the acidic aqueous solution. Thus they are detected in

the acid chloroform extract. Structure of purine alkaloids:

N

N

N

N

O

O

CH3

CH3

CH3

N

N

N

N

O

O

H

CH3

CH3

NH

N

N

N

O

O

CH3

CH3

Caffeine Theobromine Theophylline

33. Alkaloid poisoning occurred. The positive reactions with general

sedimentation reagents were obtained when analyzing the acid chloroform

extract. What substance presence can be suspected?

A. Morphine

B. Atropine

C. Quinine

60

D. Caffeine

E. Codeine

34. Caffeine poisoning occurred. The Murexide Test resulted in forming a

pink colour when testing the acid chloroform extract. Which drug could

interfere with the caffeine detection by this reaction?

A. Phenobarbital

B. Strychnine

C. Atropine

D. Quinine

E. Nicotine

NB! Purine alkaloids are extensively metabolized, their metabolism involves

N-demethylation and oxidation of the 8-carbon to uric acid derivatives. Thus in adults

approximately 90 % of theophylline is metabolized in the liver mainly undergoing

8-hydroxylation to 1,3-dimethyluric acid.

N

N NH

NCH3

CH3

O

O

N

N NH

NH

CH3

O

O

H

N

NH

NH

NH

O

O

CH3

O

N

N NH

NH

O

O

CH3

O

CH3

theophylline

3-methylxanthine

(10-15%)1-methylxanthine

(15-20%)

1,3-dimethyluric acid

(45-55%)

35. The main product of Theophylline metabolism is:

A. 1,3-dimethyluric acid

B. 1-methylxanthine

C. 1-methyluric acid

D. 3-methyluric acid

E. 1,7-dimethylxanthine

Chemicotoxicological analysis of pyrazolones

36. Which drug can be detected in the acid chloroform extracts by the

reaction with iron (III) chloride?

A. Barbital

61

B. Caffeine

C. Antipyrine

D. Diazepam

E. Theophylline 37. Drug poisoning occurred. Which medicine can be detected in the acid

chloroform extracts by the reaction with iron (III) chloride?

A. Metamizole

B. Phenobarbital

C. Caffeine

D. Diazepam

E. Theophylline

Chemicotoxicological analysis of the basic chloroform extract for presence of

alkaloids NB! The traditional way of describing xenobiotic absorption is by the pH-partition

hypothesis. The hypothesis regards the passage of a poison into the blood as being by

passive diffusion of non-ionized molecules across the lipoid barrier of the cells of the

gut lining and into the blood. Thus an acidic medicine such as aspirin (pKa 3.5) is

absorbed in the stomach at about pH 2 when the poison is non-ionized. The poison

diffuses passively across a single barrier into the capillaries and is taken up by the

plasma at pH 7.4. Here, it ionizes and is, therefore, unable to return to the stomach.

Basic medicines such as ephedrine (pKa 9.6) are only slightly absorbed in the

stomach, the major part being absorbed from the upper section of the small intestine

(pH from 5 to 7), its lower section (pH from 7 to 8), or from the colon (pH from 7 to

8).

38. Absorption of xenobiotics from the gastrointestinal tract is determined

by their physico-chemical properties and the particular conditions in different

parts of the gastrointestinal tract. Alkaloids as basic substances are absorbed:

A. From the mouth

B. In the stomach

C. From the small intestine

D. From the gullet

E. From the large intestine

62

39. Unknown substance poisoning occurred. The positive result of the

reactions with Dragendorff’s, Sonnenschein’s, Sheybler’s reagents were

obtained. Which substance presence could be suspected?

A. Heavy metal salts

B Ammonia and its salts

C Carboxylic acids

D Phenols

E Alkaloids and other nitrogen-containing basic compounds 40. Corps liver is delivered to toxicological laboratory for laboratory

diagnostics of drug poisoning. The reactions with Dragendorff’s, Marqui’s,

Bushard’s, Mayer’s reagents were positive. What medicine cannot be detected

by these reactions?

A. Barbamil

B. Morphine

C. Caffeine

D. Diazepam

E. Tisercin

Chemicotoxicological analysis of pyridine and piperidine alkaloids NB! Physicochemical properties of alkaloids. Majority of alkaloids as bases are

powders, which are readily soluble in organic solvents (chloroform, ether,

isopentanol), poorly soluble or practically insoluble in water. Alkaloids as salts are

readily soluble in water, poorly soluble or practically insoluble in organic solvents.

As an exception the bases of pyridine and piperidine alkaloids (arecoline, coniine,

nicotine, anabazine and pachycarpine) are colourless oily liquids, which are quickly

pitched on air; readily soluble in water and organic solvents.

41. Alkaloid poisoning occurred. Isolation of the poisonous substance from

the biological material resulted in obtaining an oily residue. The presence of

which alkaloid group can be suspected in the biological material?

A. Indole alkaloids

B. Tropane alkaloids

C. Quinoline alkaloids

D. Isoquinoline alkaloids

E. Pyridine alkaloids

63

42. Alkaloid poisoning occurred. Isolation of the poisonous substance from

the biological material resulted in obtaining an oily residue. The presence of

which alkaloid can be suspected in the biological material?

A. Codeine

B. Quinine

C. Nicotine

D. Strychnine

E. Atropine

43. Microcrystaloscopic reactions are used to confirmthe presence of

pyridine and piperidine alkaloids in the basic chloroform extract. Which reagent

do these alkaloids give the most characteristic crystals with?

A. Dragendorff’s reagent

B. Marme reagent

C. Mayer’s reagent

D. Sheybler’s reagent

E. Sonnenschein’s reagent

44. Which colour reaction is used in chemicotoxicological analysis of

anabazine and nicotine?

A. With picric acid

B. With Sonnenschein's reagent

C. With Dragendorff’sreagent

D. With Bushard’s reagent

E. With vanillin in the presence of concentrated hydrochloric acid

45. Which reaction is not used for the anabasine detection in

chemicotoxicological analysis?

A. The reaction with peroxyde

B. The reaction with formaldehyde

C. The reaction with vanillin

D. The reaction with picric acid

E. The reaction with Dragendorff’s reagent

Chemicotoxicological analysis of tropane alkaloids NB! The general pathway of tropane alkaloid metabolism is hydrolysis as they are

esters:

64

ON CH3

O OH

ON CH3

O

O

O CH3

Atropine Cocaine

About 24 % of atropine dose is present in the urine as noratropine (due to

demethylation), 15 % as atropine-N-oxide (due to oxidation), 3 % as tropic acid and

2 % as tropine (due to hydrolysis). Cocaine is rapidly inactivated in man by the

hydrolysis of one or both of the ester groupings. Cocaine is eliminated in the urine

primarily as the unchanged drug (1–9 % dependent on the urine pH),

benzoylecgonine (35–54 %) which is produced by hydrolysis of the methyl ester

bond, ecgonine methyl ester (32–49%) which is produced by hydrolysis of the

benzoyl ester bond (benzoic acid, a metabolite, appears), and ecgonine (hydrolysis of

both ester groupings).

46. The final products of cocaine metabolism are:

A. Ecgonine and benzoic acid

B. Ethylecgonine and oxalic acid

C. Trimethylecgonine and tartaric acid

D. Ecgonine and tropic acid

E. Benzoylecgonine and benzoic acid

47. Ecgonine was detected in the urine as a result of the toxicological

study. Which substance poisoning can be assumed?

A. Cocaine

B. Phenacetin

C. Caffeine

D. Phenol

E. Morphine NB! Vitali-Moren’s reaction is general for the esters of tropic acid (such as atropine,

scopolamine). Though some other drugs (strychnine, an indole alkaloid, diprazine, a

phenothiazine, dicainum, a derivative of p-aminobenzoic acid) also give positive

result of this reaction.

48. Drug poisoning occurred. Vitali-Moren’s reaction was positive when

studying the basic chloroform extract. Which substance poisoning can be

assumed?

A. Morphine

65

B. Quinine

C. Ephedrine

D. Atropine

E. Nicotine 49. Vitali-Moren’s reaction is positive for some poisonous substances.

Which drugs can be detected by this reaction?

A. Strychnine, atropine, scopolamine

B. Morphine, codeine, dionin

C. Pachycarpine, nicotine, anabazine

D. Quinine, quinidine

E. Aminazine, diprazine, diazolinum

50. The extract from the biological material is analyzed for the presence of

a basicsubstance. Which drug does not give Vitali-Moren’s reaction?

A. Atropine

B. Aminazine

C. Dicainum

D. Strychnine

E. Diprazine

Chemicotoxicological analysis of quinoline alkaloids

51. Forensic toxicological analysis for alkaloids is carried out. A blue

fluorescence was observed as a result of adding sulphuric acid solution to the

aqueous extract from the biological sample. Which drug can be suspected?

A. Atropine

B. Quinine

C. Scopolamine

D. Morphine

E. Ephedrine

52. The lethal alkaloid poisoning occurred. Which alkaloid could be

quantitatively determined by the fluorescence intensity of its sulphuric acid

solution?

A. Morphine

B. Codeine

C. Quinine

66

D. Strychnine

E. Atropine 53. Quinine overdose causes serious disturbances of the central nervous

system. For quinine detection in the biological extracts the erythroquinine

reaction is used. At the positive result of this reaction the solution examined

turns:

A. Pink

B. Yellow

C. Black

D. Blue

E. Brown

Chemicotoxicological analysis of isoquinoline alkaloids NB! Let's define some terms. Opioids are psychoactive chemicals that work by

specific binding to opioid receptors and narcotic analgesics in clinical manifestations.

Natural alkaloids (morphine, codeine) found in the resin of the opium poppy

(Papaver somniferum) and semi-synthetic derivatives that are obtained by further

chemical treatment of morphine (acetylation – heroin (diacethylmorphine), alkylation

– dionin (ethylmorphine), etc.) are considered to be opiates. Synthetic opioids are

fentanyl and its derivatives, promedol, tramadol, methadone, buprenorphine,

naloxone, naltrexone, etc. Morphine and codeine, as well as their synthetic

derivatives, contain the phenanthrene isoquinoline heterocycle:

O

OH

OCH

3

NCH

3

O

OH

OH

NCH

3

codeinemorphine

O

NCH

3

O

CH3

O

CH3

героїн

O

NCH

3

H5C

2O

OH

діонін

. HCl. 2H2O

heroin dionin

67

54. Most narcotic and drastic substances are obtained from the plant raw

material. Which substance listed below is obtained synthetically or semi-

synthetically?

A. Morphine

B. Codeine

C. Narcotine

D. Heroin

E. Papaverine NB! Opium in a variety of dosage forms (tinctures, extracts, tablets) for a long time

was widely used in medicine as a painkiller, but because of pronounced narcotic

effect and high toxicity it was removed from usage. Opium (poppy tears, lachryma

papaveris) is the dried latex obtained from the unripe poppy heads of opiumpoppy. It

contains more than 20 alkaloids (3–20 % morphine, codeine (0.2–2 %), papaverine

(0.1–1.5 %), narcotine (0.75–9 %), narceine, thebaine et al.), and a number of other

substances, the main ones are proteins, carbohydrates, acids and some other

substances of acidic nature (meconic acid, meconium):

CH

CO

C

CC

O

OH

COOHHOOC H

3CO

H3CO

CO

CH2

O

meconic acid meconium

55. Opium alkaloids cause severe poisonings because of their high toxicity.

The main opium alkaloid is:

A. Morphine

B. Codeine

C. Papaverine

D. Anabazine

E. Strychnine NB! The evidence of the opium presence in the sample being analysed is the

detection of morphine, codeine, narcotine, meconic acid and meconium.

56. Opiate poisoning occurred. Which substance should be detected in

order to prove the presence of opium and not morphine in the sample?

A. Hydrochloric acid

68

B. Tropic acid

C. Salicylic acid

D. Acetic acid

E. Meconic acid

NB! Omnopon is a mixture of five opium alkaloids (morphine 50 %, codeine 2.5-

5 %, narcotine 16-22 %, papaverine 2.5-7 %, thebaine 0.4% as hydrochlorides). It

does not contain meconic acid meconium. Omnopon is used in medicine mainly for

the same purpose as morphine. It is believed that this mixture of alkaloids depresses

respiration in less degree than morphine.

57. Narcotic poisoning occurred. Which substance should the reaction be

carried out on to prove that the sample contained opium and not omnopon?

A. Morphine

B. Meconic acid and meconium

C. Papaverine

D. Thebaine

E. Codeine NB! Narcotine does not have narcotic and analgesic properties, so it is not used as an

individual drug in medicine. However, this alkaloid is a component of the opium and

omnopon. Narcotine detection in the biological samples is one of the evidence of the

opium or omnopon poisoning.

58. Narcotine should be detected in the case when the following drug

presence is suspected in the extract from the biological material:

A. Morphine

B. Cocaine

C. Nicotine

D. Heroin

E. Atropine NB! In blood heroin (diacetylmorphine) rapidly hydrolyzes to 6-O-

monoacetylmorphine and then to morphine. Heroin is more toxic than morphine. Its

use in medicine is prohibited in many countries. Frequent and regular administration

is associated with tolerance and physical dependence. Internationally,

diacetylmorphine is controlled under Schedules I and IV of the Single Convention on

Narcotic Drugs.

69

59. Heroin administrated an organism is metabolized mainly to:

A. Codeine

B. 3-monoacetylmorphine

C. 6-monoacetylmorphine

D. 6-monoacetylmorphine and morphine

E. 3-monoacetylmorphine and morphine NB! Codeine is biotransformed in man via O-demethylation to morphine and via N-

demethylation to norcodeine. All three compounds are excreted in the urine as both

free drugs and as glucuronide conjugates; over 95 % of a single dose is eliminated in

48 hours.

60. When the forensic toxicological studies are performed it should be

taken into account that the codeine biotransformation product is:

A. Morphine

B. Ethylmorphine

C. Heroin

D. Thebaine

E. Papaverine

61. Opium poisoning occurred. When studying the basic chloroform

extract it should be taken into account that the codeine biotransformation

product is:

A. Papaverine

B. Thebaine

C. Heroin

D. Ethylmorphine

E. Morphine NB! Papaverine, an isoquinoline alkaloid derived from opium, vasodilator and

antispasmolic is used in the treatment of spasm of blood vessels and muscles of the

abdomen. Its molecule contains the benzylisoquinoline heterocycle:

N

H3СO

H3СO

OСH3

OСH3

papaverine

70

Biotransformation of papaverine includes O-demethylation to form phenolic

compounds which are excreted in urine as glucuronides.

62. The main pathway of papaverine biotransformation is:

A. Acetylation

B. N-methylation

C. O- methylation

D. O-demethylation

E. Hydroxylation NB! Group reagent for opiates is Marqui’s reagent (sulphuric acid concentrated and

formaldehyde). Violet, green and other colour appears.

63. Express-testing the biological extract for presence of opium is carried

out. Which reagent should be used?

A. Concentrated sulphuric acid

B. Concentrated perchloric acid

C. Marqui’s reagent

D. Strong dark blue solution

E. Potassium iodide solution NB! Pellagri reaction was used primary for apomorphine detection. Morphine and

codeine when heated with concentrated hydrochloric and sulphuric acids are

converted into apomorphine. The resulting solution is neutralized with a sodium

carbonate solution and an alcoholic solution of iodine is added. In this case, a green

colour appears. After adding diethyl ether and shaking, the aquous layer retains a

green colour, and the etheric one becomes purple-red. This reaction is suitable for

detection of morphine, codeine, heroin and dionine.

64. Which compound listed below gives the positive result of Pellagri

reaction?

A. Caffeine

B. Codeine

C. Papaverine

D. Quinine

E. Cocaine NB! Promedol gives the positive reactions with general sedimentation reagents and

with Marqui’s reagent (red colour).

71

65. Liver, blood and urine were delivered to laboratory for forensic-

toxicological study. Which reaction should be used to prove the presence of

promedol in the basic chloroform extract?

A. Pellagri reaction

B. With Sonnenschein’s reagent

C. With Mayer’s reagent

D. With Marquis’s reagent

E. With picric acid NB! Morphine gives positive reactions with iron (III) chloride (violet) and iodate acid

(violet) due to the phenolic hydroxyl presence in its molecule. In the last reaction

when shaking a weak acidic solution of morphine with iodate acid solution (KIO3),

which does not contain iodide, free iodine is released. Then when adding chloroform

and shaking, the organic layer is turned into violet.

66. Opiate poisoning occurred. Which reagent should be used to

distinguish morphine and codeine?

A. Dragendorff’s reagent

B. Pellagri reagent

C. Iodate acid

D. Hydrogen peroxyde

E. Picric acid

67. Opiate poisoning occurred. Which reagent should be used to

distinguish morphine and codeine?

A. Dragendorff’s reagent

B. Pellagri reagent

C. Iron (III) chloride

D. Hydrogen peroxyde

E. Picric acid

Chemicotoxicological analysis of indole alkaloids

68. Froehde reagent is used for detection of various alkaloids extracted from

the biological material. Which substance does not give the reaction with this

reagent?

A. Strychnine

B. Morphine

72

C. Papaverine

D. Heroin

E. Brucine

NB! Strychnine is a weak base (pKa = 8.26). So it is extracted with chloroform from

acidic and alkaline aqueous solutions. The structure of strychnine:

69. Alkaloid poisoning is occurred. Which alkaloid is extracted by

chloroform from the acidic and alkaline aqueous solutions?

A. Morphine

B. Quinine

C. Cocaine

D. Papaverine

E. Strychnine

Chemicotoxicological analysis of acyclic alkaloids

NB! Ephedrine, an acyclic alkaloid, is a secondary amine:

CH3

OH

NHCH

3

Ephedrine is metabolized in human primarily by N-demethylation to norephedrine

(phenylpropanolamine) and probably to a minor extent by p-hydroxylation and

conjugation. In normal subjects, from 70–80 % of a dose is eliminated unchanged in

the 48-hour urine and about 4 % is present as norephedrine.

70. Analysis of the biological extract resulted in the detection of

phenylpropanolamine. Which alkaloid is it a metabolite of?

A. Rezerpine

B. Pyrocatechine

C

CH2

N

C

CH2

CH

CN

CCH

2

C

C

O

CH2

CH2

CH

O CH2

HHH

H

73

C. Akonitine

D. Securinine

E. Ephedrine

71. Ephedrine, an acyclic alkaloid, is excreted mainly unchanged in the

urine. A certain part of ephedrine is metabolized to phenylpropanolamine by:

A. O-demethylation

B. N-demethylation

C. O-dealkylation

D. S-dealkylation

E. Hydroxylation NB! Ninhydrin (2,2-dihydroxyindane-1,3-dione) is a reagent used to detect ammonia

or primary and secondary amines. When reacting with these amines, a deep blue or

purple color is produced. Ninhydrin is most commonly used to detect fingerprints, as

the terminal amines of lysine residues in peptides and proteins sloughed off in

fingerprints react with ninhydrin. 72. Which reagent is used for visualization of ephedrine in TLC drug

screening?

A. Concentrated sulphuric acid

B. Concentrated perchloric acid

C. Marqui’s reagent

D. Ninhydrin acetone solution

E. Iron (III) chloride

Chemicotoxicological analysis of phenothiazine derivatives

73. Phenothiazines can result in acute poisonings. Which substance is not a

phenothiazine derivative?

A. Diprazine

B. Dicainum

C. Levomepromazine

D. Propazine

E. Aminazine

NB! The metabolism of phenothiazines is exceedingly complex; for example, 168

possible metabolites of aminazine have been postulated and at least 20 of these have

been isolated. Less than 1 % of a dose of aminazine or levomepromazine is excreted

74

unchanged in the 24-hour urine. The elimination of the medecine from the body is

very slow, and metabolites have been identified in the urine of patients as long as 18

months after discontinuation of therapy. The main pathways of phenothiazine

biotransformation are N-demethylation (and O-demethylation for levomepromazine),

sulphoxidation, phenolic hydroxylation at positions 3 and 6 followed by the

glucuronide conjugation.

N

S

CH3

N(CH3)

2

N

S

CH3

N(CH3)

2

O

N

S

CH3

N(CH3)

2

OO

diprazine sulphoxide sulphone

74. Diprazine, a psychotic drug, has the additive effect with the narcotic

and sleeping drugs. Diprazine poisoning can be diagnosed even in 14 days by the

presence of the following metabolite in the urine:

A. Sulphoxide

B. Phenylpropanolamine

C. Diethylaminoethanol

D. p-Aminobenzoic acid

E. p-Aminophenol

75. Which group of drugs is metabolized by sulphur oxidization?

A. Phenothiazine derivatives

B. Tropane derivatives

C. Quinoline derivatives

D. Benzodiazepine derivatives

E. Purine derivatives NB! The preliminary test for phenothiazines is the reaction with FPN reagent (mix

together 5 ml of ferric chloride solution, 45 ml of 20 % perchloric acid solution and

50 ml of 50 % nitric acid solution). Phenothiazines give pink and violet colour.

Phenothiazines give positive reactions with general sedimentation reagents and the

range of colour tests: with concentrated acids (H2SO4, HNO3, HCl, HClO4),

Froehde’s, Mandelin’s, Maqui’s reagents, FeCl3, NaNO2 solutions.

75

76. The aminazine poisoning is suspected. The preliminary test for

phenothiazines is the reaction with:

A. FPN reagent

B. Bromine water

C. Nitric acid

D. 5 % KMnO4 solution

E. Bushard reagent

77. Thin Layer Chromatography is used for aminazine detection in

toxicological studies. Which reagent is not used for aminazine visualization?

A. Marqui’s reagent

B. Iron (III) chloride solution

C. Dragendorff’s reagent

D. Diphenylcarbazide chloroform solution

E. Iodine vapour

Chemicotoxicological analysis of 1,4-benzodiasepine derivatives

NB! The basic routes of benzodiazepine metabolism are hydroxylation followed by

the glucuronidation, N-demethylation, reduction, hydrolysis. Hydrolysis of

1,4-benzodiazepines results in 2-aminobenzophenon formation:

NH2

Cl

C6H

5

ON

NH

Cl

O

C6H

5

OHNH

2

OH

COOH

2-amino-5-chlorobenzophenonoxazepam

H2O

+

78. The forensic toxicological study could be carried out by the

metabolism products of the toxic substances. Aminobenzophenones are

biotransformation products of:

A. Phenothiazines

B. Barbiturates

C. 1,4-Benzodiazepines

D. Butyrophenones

E. Opiates NB! Aromatic primary amines could be converted into its diazonium salts

(diazotization process), then diazonium salts undergo coupling reactions to form azo

dyes:

76

NH2

C

C6H

5

OCl

N+

C

C6H

5

OCl

N Cl

OH

NHNH

2

N

C

C6H

5

OCl

N

OH

N

C

C6H

5

OCl

N

NH

NH2

HCl

NaNO2

2-amino-5-chlorobenzophenon the salt of diazonium

an orange colour a pink-lilac colour

In chemicotoxicological analysis Azo coupling reaction is used for benzodiasepine

detection by the product of its acidic hydrolysis.

79. When examining the basic chloroform extract for 1, 4-benzodiasepine

presence the reaction with β-naphtol resulted in an orange colour appearance.

Which substance gives the positive Azo coupling reaction?

A. Aminobenzophenone

B. Methylaminobenzofenone

C. Oxazepam

D. Nitrazepam

E. Diazepam

Chemicotoxicological analysis of p-aminobenzoic acid derivatives

NB! In organism Novocaine (Procaine) is readily hydrolyzed in plasma, primarily by

plasma esterases, to p-aminobezoic acid and diethylaminoethanol: NH

2

OON

C2H

5

C2H

5

NH2

OHO

OHN

C2H

5

C2H

5H2O, t

+

80. At the toxicological study p-aminobenzoic acid was detected. Which

substance could be the reason of the poisoning?

A. Promedol

B. Aminazine

C. Chlorodiazopoxide

D. Novocaine

E. Rezerpine

77

TOPIC: GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIAL BY EXTRACTION WITH WATER

NB! Nitrates are converted by intestinal flora to nitrites that oxidize ferrous

hemoglobin to ferric methemoglobin.

1. Nitrites and nitrates are toxic substances. Considerable amounts of

nitrite induce formation in an organism:

A. Dezoxyhemoglobin

B. Oxyhemoglobin

C. Carboxyhemoglobin

D. Oxymioglobin

E. Methhemoglobin

2. Poisoning by an unknown substance happened. When testing the

biological material, it was determined that the pH values of the sample was 2-3.

Which substances can be suspected?

A. Mineral acids or a lot of organic acids

B. Alkalis

C. Ammonia

D. Weak organic acids and salts of heavy metals

E. Salts of alkaline metals NB! The general isolation method of mineral acids, alkalis and salts of alkaline

metals from the biological material is extraction (infusion) with water.

3. In toxicological chemistry poisons are divided into groups according to

their isolation method from the biological material. Which group of poisons

according to the isolation method does hydrochloric acid belong to? Group of

substances isolated by:

A. Steam distillation

B. Extraction with water

C. Extraction with acidified water

D. Some special method

E. Substances which are determined in the sample without isolation

78

4. In toxicological chemistry poisons are divide into groups according to

their isolation method from the biological sample. Which group of poisons

according to the isolation method does nitrites and nitrates belong to? Group of

substances isolated by:

A. Steam distillation

B. Extraction with water

C. Extraction with acidified water

D. Some special method

E. Substances which are determined in the sample without isolation 5. Mineral acids, alkalis and salts of alkaline metals are isolated from the

biological samples by the followed method:

A. Microdiffusion

B. Extraction with polar solvents

C. Infusion of the biological material with water

D. Infusion of the biological material with organic solvents

E. Substances which can be determined in the biological sample without

isolation

6. Poisoning by a mineral acid happened. What method is used for

isolation of mineral acids from the biological material?

A. Steam distillation

B. Mineralization

C. Infusion with water

D. Extraction by an organic solvent

E. Extraction by a polar solvent

7. Child outpoured on itself concentrated sulfuric acid. His shirt was sent

for toxicological study. What method is used for the isolation of this substance

from the sample:

A. Extraction by an organic solvent

B. Mineralization

C. Steam distillation

D. Infusion with water

E. Extraction by benzene

79

8. For isolation of particular poisons from the biological material various

methods are used. Alkalis and ammonia are isolated by:

A. Infusion with water followed by the dialysis

B. Mineralization followed by the denitration

C. Microdiffusion

D. Infusion with acidified ethanol

E. Infusion with an organic solvent

9. Nitrite and nitrate are isolated from the biological samples by extraction

with water. What method is used for purification of the aqueous extracts

obtained from the biological admixtures?

A. TLC

B. Extraction

C. Distillation

D. Dialysis

E. Electrophoresis

10. For isolation of alkalis from the biological material the method of

infusion with water is used. The aqueous extracts obtained are filtered and

purified by the following method:

A. Sublimation

B. Thin layer chromatography

C. Extractions by an organic solvent

D. Distillations

E. Dialysis

11. What purification method from admixtures is used after isolation of

nitrites and nitrates from the biological sample by extraction with water?

А. Extraction

B. Sublimation

C. Dialysis

D. Gel-chromatography

E. Thin layer chromatography

12. After extraction of the mineral poisons from the biological material by

water the purification by dialysis was carried out. Dialysis is a process of:

А. Membrane filtration

80

B. Sorbtion

C. Substitution

D. Sedimentation

E. Complexation NB! For isolation of concentrated sulphuric acid from clothes the specific isolation

method is developed. It is the infusion of the sample with ethanol.

13. A charred shirt is delivered to the laboratory for toxicological study.

Which method is used for the isolation of sulphuric acid from clothes?

A. Infusion with water

B. Infusion with ethanol

C. Distillation

D. Mineralization

E. Dialysis

14. Toxicological study is carried out. Which acid is detected by the

reaction with diphenylamine?

A. Sulphuric acid

B. Hydrochloric acid

C. Nitric acid

D. Phosphoric acid

E. Boric acid

15. Nitrite poisoning happened. Detection of nitrite in the extract is carried

out using the following reagent:

A. Griss reagent (sulphanilic acid and α-naphthyl amine)

B. Dragendorff’s reagent

C. Marqui’s reagent

D. Nessler’s reagent

E. Fehling’s reagent 16. Nitrite poisoning happened. What acid is used for detection of nitrtite

by azodye coupling reaction?

A. Sulphuric

B. Sulphurous

C. Sulphanilic

D. Hydrochloride

E. Salicylic

81

17. Toxicological study for nitrite and nitrate is carried out. Which

reaction allows to distinguish nitrite and nitrate?

A. With Griss reagent

B. With diphenylamine

C. With brucine

D. With ferric (III) chloride and sulphuric acid concentrated

E. With Nessler’s reagent

18. Potassium salt poisoning happened. Which reagent is used for

detection of potassium ions in the dialysate?

A. Dithizone

B. Sodium hydrotartrate

C. Nessler’s reagent

D. Fehling’s reagent

E. Uranyl zinc acetate

19. At the strong alkaline medium of the aqueous extract from the

biological material and at the absence of carbonate and ammonium salt the

presence of alkalis can be suspected. To confirm the presence of potassium

hydroxide a toxicologist should use the following reaction for sodium ions:

A. With Griss reagent

B. With Nessler’s reagent

C. With potassium antimonite (V)

D. With sodium hydrotatrate

E. With uranyl zinc acetate

For notes:

82

TOPIC: SUBSTANCES DETERMINED IN THE BIOLOGICAL MATERIAL

WITHOUT ISOLATION (CARBON MONOXIDE)

1. Poisoning by carbon monoxide happened. Which compound appears in

a living organism exposed to this gas?

A. Carboxyhemoglobin

B. Oxyhemoglobin

C. Methemoglobin

D. Dezoxyhemoglobin

E. Mioglobin

2. Different poisons are isolated from the biological samples using various

methods. Carboxyhemoglobin is detected and determined:

A. After isolation from kidneys by infusion with ethanol

B. After isolation from lungs by steam distillation

C. After isolation from blood by dialysis

D. After isolation from liver by mineralization

E. Directly in blood without preliminary isolation

3. Carbon monoxide poisoning happened. In order to isolate and detect

this substance in the biological material it is necessary to:

A. Isolate by infusion with acidified water and then to detect

B. Isolate by mineralization and then to detect

C. Isolate by steam distillation and then to detect

D. Detect it directly in the biological sample without preliminary isolation

E. Isolate by infusion with acidified alcohol and then to detect

4. When detecting a toxic substance in the blood toxicologist adds 2 ml of

0.01 % potassium bichromate solution and 5 drops of 20 % potassium

ferrocyanide (III) solution in two test tubes containing equal volumes of diluted

blood. In the first test tube the blood examined retains its red colour and in the

other one it is turned into brown-green. Toxicologist can conclude that the blood

in the second test tube contains the following poisonous substance:

A. Atropine

B. Caffeine

C. Hexenal

D. Concentrated nitric acid

E. Carbon (II) oxide

83

5. Quantitative determination of carbon (II) oxide in the blood by

spectrophotometric method is based on differences between spectra of the

following compounds:

A. Carboxyhemoglobin and dezoxyhemoglobin

B. Oxyhemoglobin and carboxyhemoglobin

C. Carboxyhemoglobin and methemoglobin

D. Methemoglobin and oxyhemoglobin

E. Oxyhemoglobin and dezoxyhemoglobin

6. For quantitative determination of carbon (II) oxide in the blood the

spectrophotometric method by V. Ph. Kramarenko can be used. In this method

the following spectra are compared:

A. Dezoxyhemoglobin and methohyhemoglobin

B. Oxyhemoglobin and methoxyhemoglobin

C. Carboxyhemoglobin and methoxyhemoglobin

D. Oxyhemoglobin and dezoxyhemoglobin

E. Dezoxyhemoglobin and carboxyhemoglobin

7. Determination of carboxyhemoglobin by spectrophotometric method is

possible to carry out in corpse material if the sample is:

A. Fresh

B. Rotting

C. Saved no more than 10 days

D. Fresh or saved no more than 10 days

E. Burnt

8. Toxicological examination of blood for the presence of

carboxyhemoglobin is carried out. What reagent is used for transformation of

oxyhemoglobin to dezoxyhemoglobin?

A. Urea

B. Formaldehyde

C. Sodium salphate

D. Sodium phosphate

E. Sodium sulphide

84

TABLES FOR SELF-CONTROL OF ANSWERS ON TEST TASKS

(REFERENCE REPLIES)

Question Answer Question Answer

INTRODUCTION INTO TOXICOLOGICAL CHEMISTRY. GENERAL

RULES OF POISON BEHAVIOUR IN A BODY

1 D 9 A

2 B 10 D

3 B 11 B

4 E 12 A

5 E 13 E

6 C 14 C

7 B 15 C

8 C 16 D

GROUP OF SUBSTANCES ISOLATED FROM BIOLOGICAL MATERIAL

BY MINERALIZATION (METALLIC POISONS)

1 D 36 D

2 B 37 B

3 C 38 C

4 A 39 E

5 B 40 C

6 E 41 B

7 E 42 D

8 B 43 B

9 C 44 A

10 D 45 E

11 C 46 C

12 E 47 A

13 E 48 C

14 C 49 B

15 A 50 A

16 D 51 E

17 B 52 B

18 E 53 C

19 B 54 B

20 C 55 D

21 B 56 C

22 A 57 C

23 E 58 D

24 C 59 D

25 B 60 A

26 A 61 B

27 A 62 C

85

28 C 63 B

29 D 64 B

30 A 65 D

31 C 66 E

32 B 67 E

33 C 68 C

34 E 69 D

35 D 70 A

GROUP OF SUBSTNCES ISOLATED FROM BIOLOGICAL MATERIAL BY

STEAM DISTILLATION (VOLATILE POISONS)

1 B 30 E

2 D 31 B

3 C 32 C

4 E 33 D

5 A 34 E

6 D 35 A

7 B 36 D

8 B 37 A

9 C 38 B

10 D 39 C

11 A 40 B

12 E 41 E

13 C 42 D

14 D 43 A

15 E 44 C

16 C 45 C

17 B 46 B

18 A 47 D

19 D 48 D

20 C 49 A

21 D 50 B

22 B 51 E

23 B 52 D

24 E 53 E

25 A 54 B

26 C 55 C

27 D 56 A

28 C 57 D

29 B

GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIAL BY ORGANIC SOLVENT EXTRACTION (PESTICIDES)

1 C 16 D

2 B 17 A

86

3 E 18 E

4 D 19 B

5 A 20 C

6 B 21 C

7 E 22 B

8 C 23 B

9 A 24 B

10 B 25 C

11 D 26 A

12 B 27 E

13 E 28 A

14 C 29 D

15 C

GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIAL BY SOLVENT EXTRACTION (DRUGS)

1 C 41 E

2 E 42 C

3 A 43 A

4 B 44 E

5 A 45 B

6 B 46 A

7 D 47 A

8 A 48 D

9 C 49 A

10 D 50 B

11 E 51 B

12 D 52 C

13 A 53 A

14 A 54 D

15 E 55 A

16 C 56 E

17 C 57 B

18 B 58 A

19 A 59 D

20 E 60 A

21 A 61 E

22 B 62 D

23 A 63 C

24 B 64 B

25 A 65 D

26 E 66 C

27 A 67 C

28 D 68 A

87

29 C 69 E

30 E 70 E

31 A 71 B

32 E 72 D

33 D 73 B

34 A 74 A

35 A 75 A

36 C 76 A

37 A 77 D

38 C 78 C

39 E 79 A

40 A 80 D

GROUP OF SUBSTANCES ISOLATED FROM THE BIOLOGICAL

MATERIAL BY EXTRACTION WITH WATER

1 E 11 C

2 A 12 A

3 B 13 B

4 B 14 C

5 C 15 A

6 C 16 C

7 D 17 A

8 A 18 B

9 D 19 E

10 E

SUBSTANCES DETERMINED IN THE BIOLOGICAL MATERIAL

WITHOUT ISOLATION (CARBON MONOXIDE)

1 A 5 A

2 E 6 E

3 D 7 D

4 E 8 E

88

LITERATURE

Basic

1. Bondar, V. S. Toxicological chemistry. Schemes and Tables: Handbook for

students of higher schools / V. S. Bondar, S. A. Karpushina. – Kharkiv : NUPh

: Golden Pages, 2009. – 120 p.

2. Karpushina, S. A. Toxicological chemistry. Lecture course / S. A. Karpushina,

V. S. Bondar, I. A. Zhuravel. – Kharkiv : NUPh : Golden pages, 2011. – 208 p.

3. Toxicological Chemistry. Laboratory workbook / S. A. Karpushina, I. A.

Zhuravel, V. S. Bondar, S. V. Bayurka. – Kharkiv : NUPh, 2012. – 63 p.

Additional

1. Baselt, C. R. Disposition of Toxic Drugs and Chemicals in Man: 9-th edition /

R. C. Baselt. – California : Biomedical Publications, 2011. – 1900 p.

2. Basic Analytical Toxicology / R. J. Flanagan [et al.]. – Geneva : World Health

organization, 1995. – 363 p.

3. Bell, S. Forensic Chemistry / S. Bell. – New Jersey : Pearson Prentice Hall. –

671 p.

4. Clarke's analysis of drugs and poisons in pharmaceuticals, body fluids and

postmortem material: 4-th edition / A. C. Moffat [et al.]. – London ; Chicago :

Pharmaceutical Press, 2011. – 2736 p.

5. Clarke’s Analytical Forensic Toxicology / ed. by Sue Jickells, Adam Negrusz.

– London : Pharmaceutical Press, 2008. – 648 p.

6. Flanagan, R. J. Developing Analytical Toxicology Services: Principles and

Guidance [Electronic resource] / R. J. Flanagan. – Geneva : World Health

Organization, 2005. – 36 p. – Available at :

http://www.who.int/ipcs/publications

/training_poisons/hospital_analytical_toxicology.pdf (date of the application :

(07.09.2017). – Developing Analytical Toxicology Services: Principles and

Guidance.

7. Poisoning & Drug Overdose. Fourth Edition / ed. by Kent R. Olson. – Zange

Medical Books, Mc Graw-Hill, 2004. – 718 p.

89

FOR NOTES:

90

FOR NOTES:

91

FOR NOTES:

92

Збірка тестових питань з токсикологічної хімії, що містить відповіді та пояснення,

призначена для індивідуальної роботи іноземних студентів спеціальності 8.12020101

«Фармація», які навчаються англійською мовою. Збірка включає в себе тести з наступних

тем: Вступ у токсикологічну хімію; Закономірності поведінки отрут в організмі та

метаболізм; Металічні отрути; Леткі отрути; Пестициди; Лікарські речовини; Мінеральні

кислоти, луги, нітрати та нітрити; Чадний газ. Висвітлено теоретичні та практичні аспекти

токсикокінетики, пробопідготовки, токсикологічного скринінгу, ідентифікації та кількісного

визначення отруйних речовин. Видання рекомендується для фармацевтичних факультетів та

фармацевтичних університетів III-IV рівнів акредитації.

Навчальне видання

Карпушина Світлана Анатолівна

Нетьосова Кристина Юріївна

Баюрка Сергій Васильович

ТОКСИКОЛОГІЧНА ХІМІЯ

Збірка тестів

Англійською мовою