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Details

Stereochemistry RACEMIC
Molecular Formula C15H23NO2
Molecular Weight 249.3492
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N,O-DIDESMETHYLVENLAFAXINE

SMILES

CNCC(c1ccc(cc1)O)C2(CCCCC2)O

InChI

InChIKey=MMSWXJSQCAEDLK-UHFFFAOYSA-N
InChI=1S/C15H23NO2/c1-16-11-14(12-5-7-13(17)8-6-12)15(18)9-3-2-4-10-15/h5-8,14,16-18H,2-4,9-11H2,1H3

HIDE SMILES / InChI

Molecular Formula C15H23NO2
Molecular Weight 249.3492
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

N,O-Didesmethylvenlafaxine is a metabolite of venlafaxine, an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. In humans, venlafaxine is biotransformed for the most part by CYP2D6 and CYP2C19 isoenzymes to its major metabolite O-desmethylvenlafaxine, and in parallel to N-desmethylvenlafaxine and N,O-didesmethylvenlafaxine. It was shown, that CYP2D6 genotype influenced the O-demethylation whereas CYP2C19 influenced the N-demethylation of venlafaxine and its metabolites.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Influence of CYP2D6 activity on the disposition and cardiovascular toxicity of the antidepressant agent venlafaxine in humans.
1999 Aug
High performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-MS/ESI) method for simultaneous determination of venlafaxine and its three metabolites in human plasma.
2007 May 1
Influence of CYP2D6 genotype on the disposition of the enantiomers of venlafaxine and its major metabolites in postmortem femoral blood.
2012 Jan 10
Reversible cardiac dysfunction after venlafaxine overdose and possible influence of genotype and metabolism.
2016 Sep

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:03:41 UTC 2021
Edited
by admin
on Sat Jun 26 08:03:41 UTC 2021
Record UNII
DYW3W9739Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N,O-DIDESMETHYLVENLAFAXINE
Common Name English
PHENOL, 4-(1-(1-HYDROXYCYCLOHEXYL)-2-(METHYLAMINO)ETHYL)-
Systematic Name English
DESVENLAFAXINE RELATED COMPOUND B [USP-RS]
Common Name English
Code System Code Type Description
USP_CATALOG
1175795
Created by admin on Sat Jun 26 08:03:42 UTC 2021 , Edited by admin on Sat Jun 26 08:03:42 UTC 2021
PRIMARY USP-RS
CAS
135308-74-6
Created by admin on Sat Jun 26 08:03:42 UTC 2021 , Edited by admin on Sat Jun 26 08:03:42 UTC 2021
PRIMARY
PUBCHEM
3451347
Created by admin on Sat Jun 26 08:03:42 UTC 2021 , Edited by admin on Sat Jun 26 08:03:42 UTC 2021
PRIMARY
FDA UNII
DYW3W9739Y
Created by admin on Sat Jun 26 08:03:42 UTC 2021 , Edited by admin on Sat Jun 26 08:03:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE INACTIVE
<5% (NODV and NODV-glucuronide); Unit: percent of amount administered
IN-VIVO
URINE
PARENT -> METABOLITE INACTIVE
MINOR