DESMETHYLDOXEPIN, (E)-

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H19NO
Molecular Weight	265.3496
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCC\C=C1\C2=CC=CC=C2OCC3=C1C=CC=C3

InChI

InChIKey=HVKCEFHNSNZIHO-MHWRWJLKSA-N

InChI=1S/C18H19NO/c1-19-12-6-10-16-15-8-3-2-7-14(15)13-20-18-11-5-4-9-17(16)18/h2-5,7-11,19H,6,12-13H2,1H3/b16-10+

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11037801

Z-N-desmethyldoxepin is an active metabolite of doxepin, a tricyclic antidepressant. Z-N-desmethyldoxepin appeared to be a terminal oxidative metabolite, in comparison with isomeric form E-N-desmethyl-doxepin, which is undergone further oxidation under the action of CYP2D6 activity.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Geometric isomerization of doxepin during its N-demethylation in humans.	1991 May-Jun	1680624
Determination of doxepin and desmethyldoxepin in human plasma using liquid chromatography-tandem mass spectrometry.	2000 May 26	10892587
Role of cytochrome P450 2D6 (CYP2D6) in the stereospecific metabolism of E- and Z-doxepin.	2000 Oct	11037801
Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers.	2002 Oct	12360109
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].	2006 Jun	16856516

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

In 'metabolic consumption' experiments with liver microsomes (having measurable CYP2D6 activity) and initial substrate concentration of 1 microM, the consumption of E-doxepin was greater than that of Z-doxepin. With N-desmethyldoxepin, quinidine inhibited the consumption of E-N-desmethyl-doxepin whereas Z-N-desmethyldoxepin appeared to be a terminal oxidative metabolite. CYP2D6 is a major oxidative enzyme in doxepin metabolism; predominantly catalysing hydroxylation with an exclusive preference for the E-isomers. The relatively more rapid metabolism of E-isomeric forms, and the limited metabolic pathways for the Z-isomers explained the apparent enrichment of Z-N-desmethyldoxepin.

Name

Type

Language

DESMETHYLDOXEPIN, (E)-

Common Name

English

TRANS-DESMETHYLDOXEPIN

Common Name

English

1-PROPANAMINE, 3-DIBENZ(B,E)OXEPIN-11(6H)-YLIDENE-N-METHYL-, (3E)-

Systematic Name

English

(E)-3-(DIBENZO(B,E)OXEPIN-11(6H)-YLIDENE)-N-METHYLPROPAN-1-AMINE

Systematic Name

English

DOXEPIN HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

DOXEPIN IMPURITY C

Common Name

English

(E)-DESMETHYLDOXEPIN

Common Name

English

1-PROPANAMINE, 3-DIBENZ(B,E)OXEPIN-11(6H)-YLIDENE-N-METHYL-, (E)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

6433351