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TramadolThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 11/22/2016 Page 1 of 5SWGDRUG.org/monographs.htm
1. GENERAL INFORMATION
IUPAC Name: (1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
CAS#: 27203-92-5 and 22204-88-2
Synonyms: 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol
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)
Base C16H25NO2 263.38 Not Determined
HCl C16H25NO2 HCl 299.84 177.9
N
OH
O
CH3
CH3
CH3
TramadolThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 11/22/2016 Page 2 of 5SWGDRUG.org/monographs.htm
3. QUALITATIVE DATA
3.1 NUCLEAR MAGNETIC RESONANCE
Sample Preparation: Dilute analyte to ~11 mg/mL in D2O containing TSP for 0 ppm reference and maleic acid 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: Tramadol HCl; Lot# BCBK9246V; D2O; 400MHz
7.425
1
7.150
2
6.98
1
3.86
3
2.950
1
2.70
43
2.325
1
2.0 1.9 1.8 1.7 1.6 1.5 1.4
71
7.5 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
7114313121
maleic acid HDO
TSP
TramadolThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 11/22/2016 Page 3 of 5SWGDRUG.org/monographs.htm
3.2 GAS CHROMATOGRAPHY/MASS SPECTROMETRY
Sample Preparation: Dilute analyte ~4 mg/mL in MeOH
Instrument: Agilent gas chromatograph operated in split mode with MS detectorColumn: HP-5 MS (or equivalent); 30m x 0.25 mm x 0.25mCarrier Gas: Helium at 0.6 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 300oC 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: 150
Tune file: stune.u Acquisition mode: scanRetention Time: 12.263 min
EI Mass Spectrum: Tramadol HCl; Lot# BCBK9246V
m/z260240220200180160140120100806040
[x 1
06 ]In
tens
ity
1
2
3
2929292929292929292929292929292929292929292930303030303030303030303030303030303030303030 42424242424242424242424242424242424242424242
4444444444444444444444444444444444444444444446464646464646464646464646464646464646464646
55555555555555555555555555555555555555555555
58585858585858585858585858585858585858585858
595959595959595959595959595959595959595959596565656565656565656565656565656565656565656577777777777777777777777777777777777777777777
91919191919191919191919191919191919191919191
93939393939393939393939393939393939393939393
107107107107107107107107107107107107107107107107107107107107107107
115115115115115115115115115115115115115115115115115115115115115115 121121121121121121121121121121121121121121121121121121121121121121
145145145145145145145145145145145145145145145145145145145145145145135 150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150150
159159159159159159159159159159159159159159159159159159159159159159173173173173173173173173173173173173173173173173173173173173173173
175175175175175175175175175175175175175175175175175175175175175175188188188188188188188188188188188188188188188188188188188188188188
218218218218218218218218218218218218218218218218218218218218218218219219219219219219219219219219219219219219219219219219219219219219220220220220220220220220220220220220220220220220220220220220220220 262262262262262262262262262262262262262262262262262262262262262262
263263263263263263263263263263263263263263263263263263263263263263264264264264264264264264264264264264264264264264264264264264264264
m/z260240220200180160140120100806040
[x 1
05 ]In
tens
ity
1
2
2929292929292929292929292929292929292929292930303030303030303030303030303030303030303030
41414141414141414141414141414141414141414141
4242424242424242424242424242424242424242424244444444444444444444444444444444444444444444
4545454545454545454545454545454545454545454546464646464646464646464646464646464646464646
55555555555555555555555555555555555555555555
58585858585858585858585858585858585858585858
59595959595959595959595959595959595959595959 77777777777777777777777777777777777777777777
9191919191919191919191919191919191919191919192929292929292929292929292929292929292929292
103103103103103103103103103103103103103103103103103103103103103103105105105105105105105105105105105105105105105105105105105105105105
107107107107107107107107107107107107107107107107107107107107107107
108108108108108108108108108108108108108108108108108108108108108108121121121121121121121121121121121121121121121121121121121121121121
135135135135135135135135135135135135135135135135135135135135135135
145145145145145145145145145145145145145145145145145145145145145145148148148148148148148148148148148148148148148148148148148148148148
150
163163163163163163163163163163163163163163163163163163163163163163
188188188188188188188188188188188188188188188188188188188188188188
206206206206206206206206206206206206206206206206206206206206206206218218218218218218218218218218218218218218218218218218218218218218 220220220220220220220220220220220220220220220220220220220220220220
245245245245245245245245245245245245245245245245245245245245245245
248248248248248248248248248248248248248248248248248248248248248248262262262262262262262262262262262262262262262262262262262262262262
263263263263263263263263263263263263263263263263263263263263263263
264264264264264264264264264264264264264264264264264264264264264264
265265265265265265265265265265265265265265265265265265265265265265
159173
TramadolThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 11/22/2016 Page 4 of 5SWGDRUG.org/monographs.htm
3.3 INFRARED SPECTROSCOPY (FTIR)
Insrument: FTIR with diamond ATR attachment (1 bounce)Scan Parameters: Number of scans: 32
Number of background scans: 32Resolution: 4 cm-1
Sample gain: 8Aperture: 150
FTIR ATR (Diamond 1 Bounce): Tramadol HCl; Lot# BCBK9246V
Wavenumber (cm-1)4000 3500 3000 2500 2000 1500 1000
%Tr
ansm
ittan
ce
70
75
80
85
463463463463463463463463463463463463463463463463463463463463463463
648648648648648648648648648648648648648648648648648648648648648648
702702702702702702702702702702702702702702702702702702702702702702
777777777777777777777777777777777777777777777777777777777777777777
866866866866866866866866866866866866866866866866866866866866866866
982982982982982982982982982982982982982982982982982982982982982982
1045104510451045104510451045104510451045104510451045104510451045104510451045104510451045
1242124212421242124212421242124212421242124212421242124212421242124212421242124212421242
1288128812881288128812881288128812881288128812881288128812881288128812881288128812881288
1479147914791479147914791479147914791479147914791479147914791479147914791479147914791479
1578157815781578157815781578157815781578157815781578157815781578157815781578157815781578
1606160616061606160616061606160616061606160616061606160616061606160616061606160616061606
24842484248424842484248424842484248424842484248424842484248424842484248424842484248424842513251325132513251325132513251325132513251325132513251325132513251325132513251325132513
2604260426042604260426042604260426042604260426042604260426042604260426042604260426042604
2862286228622862286228622862286228622862286228622862286228622862286228622862286228622862
2929292929292929292929292929292929292929292929292929292929292929292929292929292929292929
3302330233023302330233023302330233023302330233023302330233023302330233023302330233023302
Wavenumber (cm-1)1900 1800 1700 1600 1500 1400 1300 1200 1100 1000 900 800 700
%Tr
ansm
ittan
ce
70
75
80
85
463463463463463463463463463463463463463463463463463463463463463463
476476476476476476476476476476476476476476476476476476476476476476
511511511511511511511511511511511511511511511511511511511511511511
569569569569569569569569569569569569569569569569569569569569569569582
582582582582582582582582582582582582582582582582582582582582582
621621621621621621621621621621621621621621621621621621621621621621648
648648648648648648648648648648648648648648648648648648648648648
702702702702702702702702702702702702702702702702702702702702702702
719719719719719719719719719719719719719719719719719719719719719719
777777777777777777777777777777777777777777777777777777777777777777
793793793793793793793793793793793793793793793793793793793793793793
866866866866866866866866866866866866866866866866866866866866866866
879879879879879879879879879879879879879879879879879879879879879879
937937937937937937937937937937937937937937937937937937937937937937
957957957957957957957957957957957957957957957957957957957957957957
982982982982982982982982982982982982982982982982982982982982982982
10071007100710071007100710071007100710071007100710071007100710071007100710071007100710071045104510451045104510451045104510451045104510451045104510451045104510451045104510451045
10741074107410741074107410741074107410741074107410741074107410741074107410741074107410741113111311131113111311131113111311131113111311131113111311131113111311131113111311131113
1136113611361136113611361136113611361136113611361136113611361136113611361136113611361136
11611161116111611161116111611161116111611161116111611161116111611161116111611161116111611176117611761176117611761176117611761176117611761176117611761176117611761176117611761176
1196119611961196119611961196119611961196119611961196119611961196119611961196119611961196
1242124212421242124212421242124212421242124212421242124212421242124212421242124212421242
1288128812881288128812881288128812881288128812881288128812881288128812881288128812881288
1315131513151315131513151315131513151315131513151315131513151315131513151315131513151315
1356135613561356135613561356135613561356135613561356135613561356135613561356135613561356
1387138713871387138713871387138713871387138713871387138713871387138713871387138713871387
1408140814081408140814081408140814081408140814081408140814081408140814081408140814081408
1433143314331433143314331433143314331433143314331433143314331433143314331433143314331433
14621462146214621462146214621462146214621462146214621462146214621462146214621462146214621479147914791479147914791479147914791479147914791479147914791479147914791479147914791479
1578157815781578157815781578157815781578157815781578157815781578157815781578157815781578
1606160616061606160616061606160616061606160616061606160616061606160616061606160616061606
TramadolThe Drug Enforcement Administration's Special Testing and Research Laboratory
generated this monograph using structurally confirmed reference material.
Latest Revision: 11/22/2016 Page 5 of 5SWGDRUG.org/monographs.htm
https://en.wikipedia.org/wiki/Tramadol
4. ADDITIONAL RESOURCES
Wikipedia