19 26 2 - SWGDRUG
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4-Androstene-3,17-dione The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material. Latest Revision: 10/28/2019 Page 1 of 5 SWGDRUG.org/monographs.htm 1. GENERAL INFORMATION IUPAC Name: androst-4-ene-3,17-dione CAS#: 63-05-8 Synonyms: 4-Androstenedione Source: DEA Reference Material Collection Appearance: White powder UV max (nm): Not determined 2. CHEMICAL AND PHYSICAL DATA 2.1 CHEMICAL DATA Form Chemical Formula Molecular Weight Melting Point ( o C) Neutral C 19 H 26 O 2 286.41 173.49 O CH 3 CH 3 O H H H
Transcript of 19 26 2 - SWGDRUG
4-Androstene-3,17-dioneThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 10/28/2019 Page 1 of 5SWGDRUG.org/monographs.htm
1. GENERAL INFORMATION
IUPAC Name: androst-4-ene-3,17-dione
CAS#: 63-05-8
Synonyms: 4-Androstenedione
Source: DEA Reference Material Collection
Appearance: White powder
UVmax(nm): Not determined
2. CHEMICAL AND PHYSICAL DATA
2.1 CHEMICAL DATA
Form Chemical Formula Molecular Weight Melting Point (oC)
Neutral C19H26O2 286.41 173.49
O
CH3
CH3 O
H
HH
4-Androstene-3,17-dioneThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 10/28/2019 Page 2 of 5SWGDRUG.org/monographs.htm
3. QUALITATIVE DATA
3.1 NUCLEAR MAGNETIC RESONANCE
Sample Preparation: Dilute analyte to ~11 mg/mL in CDCl3 containing TMS for 0 ppm reference and dimethylfumarate as quantitative internal standard.
Instrument: 400 MHz NMR spectrometerParameters: Spectral width: at least containing -3 ppm through 13 ppm
Pulse angle: 90o
Delay between pulses: 45 seconds
1HNMR: 4-Androstene-3,17-dione; Lot# G984414; CDCl3; 400MHz
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
31132231451
CHCl3
dimethylfumarate
TMS
5.76
1
2.50 2.45 2.40 2.35
5
2.10 2.05 2.00
4
1.875
1
1.75 1.50
223
1.220
3
1.151.101.051.00
11
0.925
3
4-Androstene-3,17-dioneThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 10/28/2019 Page 3 of 5SWGDRUG.org/monographs.htm
3.2 GAS CHROMATOGRAPHY/MASS SPECTROMETRY
Sample Preparation: Dilute analyte ~4 mg/mL in CHCl3
Instrument: Agilent gas chromatograph operated in split mode with MS detectorColumn: HP-5 MS (or equivalent); 30m x 0.25 mm x 0.25 mCarrier Gas: Helium at 1.5 mL/minTemperatures: Injector: 280oC MSD transfer line: 280oC
MS Source: 230oC MS Quad: 150oCOven program:
1) 100oC initial temperature for 1.0 min2) Ramp to 280oC at 12 oC/min3) Hold final temperature for 9.0 min
Injection Parameters: Split Ratio = 25:1, 1 L injectedMS Parameters: Mass scan range: 30-550 amu Threshold: 250
Tune file: stune.u Acquisition mode: scanRetention Time: 15.89 min
EI Mass Spectrum: 4-Androstene-3,17-dione; Lot# G984414
m/z280260240220200180160140120100806040
[x 1
05 ]In
tens
ity
0
1
2
3
4
5
6
7
39393939393939393939393939393939393939393939
41414141414141414141414141414141414141414141
53535353535353535353535353535353535353535353
55555555555555555555555555555555555555555555
65656565656565656565656565656565656565656565
67676767676767676767676767676767676767676767
77777777777777777777777777777777777777777777
79797979797979797979797979797979797979797979
81818181818181818181818181818181818181818181
91919191919191919191919191919191919191919191
93939393939393939393939393939393939393939393
105105105105105105105105105105105105105105105105105105105105105105
107107107107107107107107107107107107107107107107107107107107107107
109109109109109109109109109109109109109109109109109109109109109109
123123123123123123123123123123123123123123123123123123123123123123
124124124124124124124124124124124124124124124124124124124124124124
131131131131131131131131131131131131131131131131131131131131131131133133133133133133133133133133133133133133133133133133133133133133
145145145145145145145145145145145145145145145145145145145145145145
148148148148148148148148148148148148148148148148148148148148148148
150150150150150150150150150150150150150150150150150150150150150150
162162162162162162162162162162162162162162162162162162162162162162163163163163163163163163163163163163163163163163163163163163163163
11111111187187187187187187187187187187187187187187187187187187187187187187175
201201201201201201201201201201201201201201201201201201201201201201
229229229229229229229229229229229229229229229229229229229229229229 242242242242242242242242242242242242242242242242242242242242242242
244244244244244244244244244244244244244244244244244244244244244244
245245245245245245245245245245245245245245245245245245245245245245 271271271271271271271271271271271271271271271271271271271271271271
286286286286286286286286286286286286286286286286286286286286286286
287287287287287287287287287287287287287287287287287287287287287287
4-Androstene-3,17-dioneThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 10/28/2019 Page 4 of 5SWGDRUG.org/monographs.htm
3.3 INFRARED SPECTROSCOPY (FTIR)
Instrument: FTIR with diamond ATR attachment (1 bounce)Scan Parameters: Number of scans: 32
Number of background scans: 32Resolution: 4 cm-1
Sample gain: 1Aperture: 150
FTIR ATR (Diamond 1 Bounce): 4-Androstene-3,17-dione; Lot# G984414
Wavenumber (cm-1)3500 3000 2500 2000 1500 1000
%Tr
ansm
ittan
ce
75
80
85 512512512512512512512512512512512512512512512512512512512512512512
680680680680680680680680680680680680680680680680680680680680680680
870870870870870870870870870870870870870870870870870870870870870870
10161016101610161016101610161016101610161016101610161016101610161016101610161016101610161226
122612261226122612261226122612261226122612261226122612261226122612261226122612261226
1452145214521452145214521452145214521452145214521452145214521452145214521452145214521452
1615161516151615161516151615161516151615161516151615161516151615161516151615161516151615
16601660166016601660166016601660166016601660166016601660166016601660166016601660166016601731
173117311731173117311731173117311731173117311731173117311731173117311731173117311731
2820282028202820282028202820282028202820282028202820282028202820282028202820282028202820
2851285128512851285128512851285128512851285128512851285128512851285128512851285128512851
2918291829182918291829182918291829182918291829182918291829182918291829182918291829182918
2954295429542954295429542954295429542954295429542954295429542954295429542954295429542954
Wavenumber (cm-1)1900 1800 1700 1600 1500 1400 1300 1200 1100 1000 900 800 700
%Tr
ansm
ittan
ce
75
80
85
418418418418418418418418418418418418418418418418418418418418418418
459459459459459459459459459459459459459459459459459459459459459459
512512512512512512512512512512512512512512512512512512512512512512
541541541541541541541541541541541541541541541541541541541541541541
584584584584584584584584584584584584584584584584584584584584584584
657657657657657657657657657657657657657657657657657657657657657657
680680680680680680680680680680680680680680680680680680680680680680
715715715715715715715715715715715715715715715715715715715715715715
780780780780780780780780780780780780780780780780780780780780780780832
832832832832832832832832832832832832832832832832832832832832832
870870870870870870870870870870870870870870870870870870870870870870
901901901901901901901901901901901901901901901901901901901901901901
936936936936936936936936936936936936936936936936936936936936936936951951951951951951951951951951951951951951951951951951951951951951
1016101610161016101610161016101610161016101610161016101610161016101610161016101610161016
1055105510551055105510551055105510551055105510551055105510551055105510551055105510551055
1094109410941094109410941094109410941094109410941094109410941094109410941094109410941094
1130113011301130113011301130113011301130113011301130113011301130113011301130113011301130
11741174117411741174117411741174117411741174117411741174117411741174117411741174117411741195
119511951195119511951195119511951195119511951195119511951195119511951195119511951195
1226122612261226122612261226122612261226122612261226122612261226122612261226122612261226
1236123612361236123612361236123612361236123612361236123612361236123612361236123612361236
1251125112511251125112511251125112511251125112511251125112511251125112511251125112511251
1272127212721272127212721272127212721272127212721272127212721272127212721272127212721272
1295129512951295129512951295129512951295129512951295129512951295129512951295129512951295
1334133413341334133413341334133413341334133413341334133413341334133413341334133413341334
13801380138013801380138013801380138013801380138013801380138013801380138013801380138013801421
142114211421142114211421142114211421142114211421142114211421142114211421142114211421
14311431143114311431143114311431143114311431143114311431143114311431143114311431143114311452
145214521452145214521452145214521452145214521452145214521452145214521452145214521452
1470147014701470147014701470147014701470147014701470147014701470147014701470147014701470
1615161516151615161516151615161516151615161516151615161516151615161516151615161516151615
16601660166016601660166016601660166016601660166016601660166016601660166016601660166016601731
173117311731173117311731173117311731173117311731173117311731173117311731173117311731
4-Androstene-3,17-dioneThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 10/28/2019 Page 5 of 5SWGDRUG.org/monographs.htm
4. ADDITIONAL RESOURCES
Lin, Yanliang, et al. "Microbial Transformation of Phytosterol in Corn Flour and Soybean Flour to 4-Androstene-3,17-dione by Fusarium moniliforme Sheld." Bioresource Technology 100 (2009) 1864-1867.
