CHEBI:83527 - O-desmethylvenlafaxine

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ChEBI Name O-desmethylvenlafaxine
ChEBI ID CHEBI:83527
ChEBI ASCII Name O-desmethylvenlafaxine
Definition A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-hydroxyphenyl group. It is a metabolite of the drug venlafaxine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB8496834, eMolecules:8320714, Selleckchem:desvenlafaxine
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Desvenlafaxine, sold under the brand name Pristiq among others, is a medication used to treat depression. It is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class and is taken by mouth. It is recommended that the need for further treatment be occasionally reassessed. It may be less effective than its parent compound venlafaxine, although some studies have found comparable efficacy. Common side effects include dizziness, trouble sleeping, increased sweating, constipation, sleepiness, anxiety, and sexual problems. Serious side effects may include suicide in those under the age of 25, serotonin syndrome, bleeding, mania, and high blood pressure. There is a high risk of withdrawal syndrome which may occur if the dose is decreased or the medication is completely stopped. It is unclear if use during pregnancy or breastfeeding is safe. Desvenlafaxine was approved for medical use in the United States in 2008. In Europe its application for use was denied in 2009. In 2022, it was the 208th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
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Formula C16H25NO2
Net Charge 0
Average Mass 263.37520
Monoisotopic Mass 263.18853
InChI InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
InChIKey KYYIDSXMWOZKMP-UHFFFAOYSA-N
SMILES CN(C)CC(c1ccc(O)cc1)C1(O)CCCCC1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): drug metabolite

marine xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing O-desmethylvenlafaxine (CHEBI:83527) has role antidepressant (CHEBI:35469)
O-desmethylvenlafaxine (CHEBI:83527) has role drug metabolite (CHEBI:49103)
O-desmethylvenlafaxine (CHEBI:83527) has role marine xenobiotic metabolite (CHEBI:83399)
O-desmethylvenlafaxine (CHEBI:83527) is a cyclohexanols (CHEBI:23480)
O-desmethylvenlafaxine (CHEBI:83527) is a phenols (CHEBI:33853)
O-desmethylvenlafaxine (CHEBI:83527) is a tertiary amino compound (CHEBI:50996)
INN Source
desvenlafaxine ChemIDplus
Synonyms Sources
1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol ChEBI
4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol ChEBI
Manual Xrefs Databases
4380 DrugCentral
D07793 KEGG DRUG
DB06700 DrugBank
Desvenlafaxine Wikipedia
HMDB0015646 HMDB
View more database links
Registry Numbers Types Sources
4234613 Reaxys Registry Number Reaxys
93413-62-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017