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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