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UC304

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
NACRES:
NA.77
PubChem Substance ID:
329827665
UNSPSC Code:
12161501
MDL number:
MFCD01311883
Form:
solid
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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, is an active metabolite of tramadol. The enzyme key for its production is polymorphic cytochrome P450 isoenzyme 2D6 (CYP2D6).

Application

O-Desmethyltramadol has been used for the pharmacokinetic studies of tramadol metabolites in goats.
O-Desmethyltramadol may be used as an opioid to test its effect on the cytotoxic functionality of human natural killer cells. 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.

Biochem/physiol Actions

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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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
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
Dermot P Maher et al.
Anesthesia and analgesia, 128(5), 1013-1021 (2019-02-26)
The use of regional and other opioid-sparing forms of anesthesia has been associated with a decrease in the recurrence of certain malignancies. Direct suppression of human natural killer cells by opioids has been postulated to explain this observation. However, the
A B de Sousa et al.
Journal of veterinary pharmacology and therapeutics, 31(1), 45-51 (2008-01-08)
The aim of this trial was to implement a method to obtain a tool for analyses of tramadol and the main metabolite, o-desmethyltramadol (M1), in goat's plasma, and to evaluate the pharmacokinetics of these substances following intravenous (i.v.) and oral
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
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Global Trade Item Number

SKUGTIN
UC304-5MG04061837410239

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