ALCALOIZI CHINOLINICI
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Transcript of ALCALOIZI CHINOLINICI
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ALCALOIZI CHINOLINICI
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Chinae cortex – arborii de China - Cynchona succirubra; C. calyssaia; C. officinalis
– fam. Rubiaceae
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Chinae cortex
Arbore inalt de 5-15 m, cu coroana densa, frunze alterne, lung petiolate
Scoarta este astringenta, cu gust amar si miros slab caracteristic
Obtinere Prin lovirea si decorticarea
ramurilor si trunchiurilor
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Chinae cortexcompozitie chimica actiune si utilizari
20% alcaloizi sub forma de saruri ale acidului chinic
Chinina (2-etenil-4-azabiciclo[2.2.2]oct-5-il)- (6-metoxichinolin-4-il)-metanol)
Compusi polifenolici Ulei volatil
Antimalaric Antipiretic Analgezic, antiinflamator Antiaritmic (extrasistole, fibrilatii 1-1.5
g/zi) Stomahic (stimuleaza secretia salivara,
gastrica) Antiseptic
Malarie Crampe si dureri musculare Anorexie Dispepsii Gripa Extern- zgarieturi si ulcere ale pielii D: 0.3 – 0.6g – max. 2 g/zi CI. – gravide
- ulcer gastro-intestinal
Chinina
OH
OH
HO
HO COOH
acidul chinic
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Identificare R. Grahe: distilare PV vapori rosu violet condensare,
dizolvare in alcool 70º fluorescenta albastra, se accentueaza la acidulare
R. taleochinica: PV umectat cu NH3 + extractie cu Ch+tratare cu
HCl saruri de alcaloizi se trateaza cu H2O2
alcalinizare = fluorescenta verde
acidulare = fluorescenta rosie
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ALCALOIZI IZOCHINOLINICI
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Papaverina Narcotine - Noscamina
Morfina Codeina
N
izochinolina
Tebaina
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Opiul- Papaver somniferum – mac - fam. Papaveraceae
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Opiul
Flori albe, violete, rosii-purpurii, capsule dehiscente sau indehiscente, seminte alb-galbui, albastre cenusii, negre, in functie de varietate
latexul uscat la aer , obtinut prin incizii practicate in capsulele imature ale speciei Papaver somniferum
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Opium compozitie chimica
40 alcalozi (Morfina, Codeina, Papaverina, Noscapina si Tebaina) sub forma de saruri ale acidului lactic, sulfuric si meconicAlcaloizi cu nucleu izochinolinic a) n. tetrahidro-izochinolinic b) n. benzil-izochinolinic (papaverina) c) n. ftalid-izochinolinic (noscapina)Alcaloizi cu nucleu morfinanic (morfina, codeina, tebaina)
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Naturally occurringopioids
Morphine
Codeine
Tebaina
Semi-syntheticopioids
Diacetylmorphine(a.k.a. heroin)
Popular street names:chiva, diesel, smack, skag, heron,
black tar, horse, junk, jenny, brown,brown sugar, dark and H. )
Syntheticopioids
Methadone
Opioidantagonists
Naltrexone
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Opiumidentificare
Opiu+ferocianura de potasiu + sare ferica = col. albastra
Opiu + formaldehida in H2SO4 conc. = col. rosie
Opiu + FeCl3 = col. rosieOH
COOH
OOH
OHOOCO
O
HOOC
acid meconic acid comenic
-CO2
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Obtinerea alcaloizilor din opiu (morfina) 1. PV = extract apos +CaCl2 acidul meconic (restul
de alcaloizi) pp ca saruri de Ca greu solubile; alcaloizii = clorhidrati in sol. apoasa separare datorita bazicitatii diferite; alcalinizare cu amoniac
pp morfina baza
codeina baza = extractie cu benzen (Ch) 2. PV = extract apos + Ca(OH)2 (alcalinizare)
morfina = morfinat de Ca
alcaloizii ramasi = saruri de Ca insolubile
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actiune
MORFINA - Analgezic central (D.: 10 mg), usor hipnotic; la 100 mg narcotic
Ef. sec.: - greata, varsaturi
- deprima centrul tusei si al respiratiei
- dependenta
- mareste tonusul musculaturii netede a intestinului = inhiba peristaltismul = constipare
Adm.: dureri neoplazice
Morphine was first isolated in 1804 by the German pharmacist Friedrich Wilhelm Adam Sertürner, who named it "morphium" after Morpheus, the Greek god of dreams.
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actiune
CODEINA – analgetic - antitusiv (inhiba centrul tusei) Ef. Sec. - deprima centrul respirator CI. - copii sub 2 ani NOSCAPINA – antitusiv, nu deprima centrul respirator PAPAVERINA – spasmolitic (relax musculatura neteda a vasel
sanguine, tub digestiv, vezica biliara, cai urinare) - coronarodilatator (angina pectorala) - vasodilatator (colici, spasm piloric, constipatie
spastica)
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Rhoeados flos - mac de camp- Papaver rhoeas. fam. Papaveraceae
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Rhoeados flos
Planta anuala, radacina pivotanta
Funze paroase, cele bazale lanceolate, neregulat penat-divizate
Florile mari, solitare, in varful tulpinii , rosii
Fructul-capsula glabra Semintele-reniforme,
brun-inchise
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Rhoeados flos
Compozitie chimica Antocianozide Alcaloizi –0,007%
( rhoeadina)
Mucilagii
Acizi organici
Actiune expectoranta, sedativa Intrebuintari Afect respiratorii la copii
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ALCALOIZI DIIZOCHINOLINICI
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Berberis cortex- dracila- Berberis vulgaris, fam. Berberidaceae
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Berberis cortex
Radacini groase de 1-4 cm, galbene la interior
Ramurile cenusiu-galbui Frunze ovat-eliptice, cu
marginea ghimpos-serata, alterne
La baza frunzelor se gasesc cativa spini furcati
Florile galbene, grupate in raceme, cu miros neplacut
Fructul-baca rosie, cu gust acru-astringent , comestibil
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Berberidis cortex compozitie chimica actiune
Alcaloizi totali 10%
- a. benziltetrahidro-izochinolinici ( coclaurina)
- a. di-izochinolinici (berberina)- a. bisbenziltetrahidro-
izochinolinici (berbamina si izomerul ei)
Acizi polifenolcarboxilici
Antociani
Taninuri
Antimicrobian (bacteri, fungi, protozoare, virusi, si clamidia)
Antibacterian (clorhidrat de berberina –conjunctivita bacteriana)
Colecistokinetic (stimuleaza secretiile biliare)
Inhiba contractiile musculaturii netede ale inimii
Hemostatica tonic, astringent, depurativ,
diuretic
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Berberis cortex
Intrebuintari Afectiuni :
- hepatobiliare,
- digestive,
- oftalmice,
- renale,
- tahiaritmii ventriculare,
- ginecologice.
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Hydrastidis rhizoma - Hydrastidis canadensis – fam. Ranunculaceae
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Hydrastidis rhizoma
Rizomii cu sau fara radacini
Planta erbacee, perena, , rizom cilindric, scurt, orixontal, rasucit, noduros, cu numeroase tuberozitati
Radacini subtiri, friabile
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Hydrastidis rhizoma compozitie chimica actiune
Alcaloizi 3-6% - hidrastinaBaze cuaternare ( 0,5- 6 %
berberina ) si tertiare ( 0,5% canadina)
Ulei gras Amidon Fitosteroli Ulei volatil Urme de meconina
Vasoconstrictor Hemostatic si ocitocic (hidrastina) Hipotensor (berberina) Antispastic Bacteriostatic, bactericid
Ut.: - insuficienta venoasa si limfatica
– hemoragii uterine
- herpes
- afectiuni digestive
- Hiperemia conjunctivala alergica sau sezoniera
CI.: - sarcina
- Deficit de glucozo-6-fosfat dehidrogenaza
INTERACTIUNI:
- Scade absorbtia vit B
- Antagonizeaza efectul anticoagulant al heparinei
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ALCALOIZI BENZOIZOCHINOLINICI
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Curara - Chondodendron si Strychnos- curara de tigva – sp. Strychnos toxifera
- curara de tub – sp. Chondodendron tomentosum - curara de oala - sp. Chondodendron tomentosum
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Curara compozitie chimica actiune
Curara de Chondodendron – (bis-benzil – izochinolinica) tubocurarina
Curara de Strychnos - toxiferina
Paralizeaza musculatura striata:- Hipotonie musculara, senzatie de
oboseala- Atonie musculara cu conservarea
motilitatii voluntare- Paralizie cu disparitia motilitatii
voluntare- Paralizie si abolirea contractilitatiiDL 0.25 - 4 mg/kg corpUt.: chirurgie = miorelaxantReac sec.: - bronhospasm - hipersecretiiCI: - insuficienta renalaAntagonist - fizostigminaToxiferin
Caracurarina