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
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+
| Molecular Formula | C18H19NO |
| Molecular Weight | 265.3496 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Geometric isomerization of doxepin during its N-demethylation in humans. | 1991 May-Jun |
|
| Determination of doxepin and desmethyldoxepin in human plasma using liquid chromatography-tandem mass spectrometry. | 2000 May 26 |
|
| Role of cytochrome P450 2D6 (CYP2D6) in the stereospecific metabolism of E- and Z-doxepin. | 2000 Oct |
|
| Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. | 2002 Oct |
|
| [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 |
Sample Use Guides
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:17:36 UTC 2023
by
admin
on
Fri Dec 15 18:17:36 UTC 2023
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| Record UNII |
J7JTC0A5D6
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| Record Status |
Validated (UNII)
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| Record Version |
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6433351
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J7JTC0A5D6
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DTXSID60217319
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67035-76-1
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142340
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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