All Photos(1)
Synonym(s):
2-[(Dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol, O-Demethyl tramadol
Empirical Formula (Hill Notation):
C15H23NO2
CAS Number:
Molecular Weight:
249.35
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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
O-Desmethyltramadol has a high affinity towards opioid receptors and is responsible for the analgesic effect of the μ-opioid receptor
Metabolite of tramadol
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
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 )
Joomi Lee et al.
Drug design, development and therapy, 13, 1751-1761 (2019-06-20)
Aim: Tramadol is widely used to treat acute, chronic, and neuropathic pain. Its primary active metabolite, O-desmethyltramadol (M1), is mainly responsible for its µ-opioid receptor-related analgesic effect. Tramadol is metabolized to M1 mainly by the cytochrome P450 (CYP) 2D6 enzyme
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
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