O-DESMETHYL TRAMADOL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H23NO2.ClH
Molecular Weight	285.81
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of O-DESMETHYL TRAMADOL HYDROCHLORIDE

Structure Search

SMILES

Cl.CN(C)C[C@H]1CCCC[C@]1(O)C2=CC(O)=CC=C2

InChI

InChIKey=IRGWVAWLHXDKIX-PBCQUBLHSA-N

InChI=1S/C15H23NO2.ClH/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;1H/t13-,15+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C15H23NO2
Molecular Weight	249.3486
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0060997 | https://www.ncbi.nlm.nih.gov/pubmed/27758804 | https://www.ncbi.nlm.nih.gov/pubmed/16679816 | https://www.ncbi.nlm.nih.gov/pubmed/15976229 | https://www.who.int/medicines/access/controlled-substances/Tramadol.pdf?ua=1

O-Desmethyl tramadol (O-Desmethyltramadol, O-DSMT) is a metabolite of tramadol. O-Desmethyltramadol is an opioid analgesic and the main active metabolite of tramadol. (+)-O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. This metabolite is considerably more potent as a μ-opioid agonist than the parent compound. O-desmethyl tramadol, inhibits 5-hydroxytryptamine type 2C receptors expressed in xenopus oocytes. O-desmethyl tramadol inhibits functions of M(1) receptors but has little effect on those of M(3) receptors. O-desmethyl tramadol has been widely used clinically and has analgesic activity.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
Pharmacokinetic-pharmacodynamic modeling of the antinociceptive effects of main active metabolites of tramadol, (+)-O-desmethyltramadol and (-)-O-desmethyltramadol, in rats.	2000 May	10773040
Modeling of the in vivo antinociceptive interaction between an opioid agonist, (+)-O-desmethyltramadol, and a monoamine reuptake inhibitor, (-)-O-desmethyltramadol, in rats.	2000 Oct	10992001
Inhibition of CYP2D6-mediated tramadol O-demethylation in methadone but not buprenorphine maintenance patients.	2012 Nov	22369095
Effects of tramadol and o-desmethyltramadol on canine innate immune system function.	2015 May	24985318

Patents

Sample Use Guides

In Vivo Use Guide

Oral Light: 15 – 30 mg Common: 30 – 50 mg Strong: 50 – 70+ mg

Route of Administration: Oral

In Vitro Use Guide

O-desmethyl tramadol (0.1-100 uM) inhibited acetylcholine (ACh)-induced currents in oocytes expressing the M(1) receptors (half-maximal inhibitory concentration [IC(50)] = 2 +/- 0.6 uM), whereas it did not suppress ACh-induced currents in oocytes expressing the M(3) receptor. O-desmethyl tramadol inhibited the specific binding of [(3)H]quinuclidinyl benzilate ([(3)H]QNB) to the oocytes expressed M(1) receptors (IC(50) = 10.1 +/- 0.1 uM), whereas it did not suppress the specific binding of [(3)H]QNB to the oocytes expressed M(3) receptors.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:20:19 UTC 2023` Edited by `admin` on `Sat Dec 16 08:20:19 UTC 2023`
Record UNII	XL5VDC061E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

O-DESMETHYL TRAMADOL HYDROCHLORIDE

Common Name

English

PHENOL, 3-(2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)-, HYDROCHLORIDE, CIS-

Common Name

English

PHENOL, 3-((1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)-, HYDROCHLORIDE, REL-

Systematic Name

English

PHENOL, 3-((1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-HYDROXYCYCLOHEXYL)-, HYDROCHLORIDE (1:1), REL-

Systematic Name

English

O-DEMETHYLTRAMADOL HYDROCHLORIDE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID10617163