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UC304

Sigma-Aldrich

O-Desmethyltramadol

Synonym(s):

2-[(Dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol, O-Demethyl tramadol

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About This Item

Empirical Formula (Hill Notation):
C15H23NO2
CAS Number:
80456-81-1
Molecular Weight:
249.35
MDL number:
MFCD01311883
UNSPSC Code:
12161501
PubChem Substance ID:
329827665
NACRES:
NA.77

form

solid

storage temp.

2-8°C

SMILES string

CN(C)C[C@H]1CCCC[C@]1(O)c2cccc(O)c2

InChI

1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1

InChI key

UWJUQVWARXYRCG-HIFRSBDPSA-N

General description

O-Desmethyltramadol, an opioid,[1] is an active metabolite of tramadol. The enzyme key for its production is polymorphic cytochrome P450 isoenzyme 2D6 (CYP2D6).[1]

application

O-Desmethyltramadol has been used for the pharmacokinetic studies of tramadol metabolites in goats[2].
O-Desmethyltramadol may be used as an opioid to test its effect on the cytotoxic functionality of human natural killer cells.[3] It may also be used as an internal standard in gas chromatography-mass spectrometry (GC-MS) for the quantification of tramadol based derivatives from human urine samples.[4]

Biochem/physiol Actions

O-Desmethyltramadol has a high affinity towards opioid receptors[3] and is responsible for the analgesic effect of the μ-opioid receptor [5]
Metabolite of tramadol

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
475-127-2V
475-127-2
1396557
1385538
067K3250

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Michael K Herbert et al.
BMC pharmacology, 7, 5-5 (2007-03-21)
Inhibition of intestinal peristalsis is a major side effect of opioid analgesics. Although tramadol is an opioid-like analgesic, its effect on gut motility is little known. Therefore, the effect of (+)-tramadol, (-)-tramadol and the major metabolite O-desmethyltramadol on intestinal peristalsis
Tramadol.
James W S Young et al.
CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne, 185(8), E352-E352 (2013-03-20)
Marc Luginbühl et al.
Drug testing and analysis, 12(8), 1126-1134 (2020-05-13)
The World Anti-Doping Agency (WADA) and the International Testing Agency (ITA) recently announced the development and implementation of dried blood spot (DBS) testing for routine analysis in time for the 2022 Winter Olympic and Paralympic Games in Beijing. Following the
Mendel Jansen et al.
Clinical pharmacology in drug development, 7(6), 597-612 (2018-06-06)
Four randomized, double-blind, placebo-controlled, 4-period drug-drug interaction studies were conducted in healthy subjects to evaluate the pharmacokinetic and pharmacodynamic (PD) interactions between mirogabalin and commonly used central nervous system depressants. Mirogabalin or placebo was administered alone or with single-dose lorazepam
Mi Jin et al.
The Journal of pharmacy and pharmacology, 72(9), 1232-1238 (2020-05-20)
The objective of this study was to investigate the possible interaction of shikonin and β,β-dimethylacrylshikonin (DSK) with tramadol. Human liver microsome (HLM) and rat liver microsome (RLM) incubation experiments were carried out to assess the half-maximal inhibitory concentration (IC50 )
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