Skip to Content
Merck
All Photos(2)

Documents

D4526

Sigma-Aldrich

Doxepin hydrochloride

~85% E-isomer basis, ≥98% (GC), 15% Z-isomer basis, powder

Synonym(s):

11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepine hydrochloride

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C19H21NO · HCl
CAS Number:
1229-29-4
Molecular Weight:
315.84
EC Number:
214-966-8
MDL number:
MFCD00079135
UNSPSC Code:
12352200
PubChem Substance ID:
24278093
NACRES:
NA.77

Assay

≥98% (GC)

form

powder

composition

Z-isomer, 15%
E-isomer, ~85%

color

white to off-white

solubility

1 M HCl: 50 mg/mL
H2O: soluble

originator

Boehringer Ingelheim

SMILES string

Cl[H].CN(C)CC\C=C1/c2ccccc2COc3ccccc13

InChI

1S/C19H21NO.ClH/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19;/h3-6,8-12H,7,13-14H2,1-2H3;1H/b17-11+;

InChI key

MHNSPTUQQIYJOT-SJDTYFKWSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133) , HRH1(3269) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR5B(645694) , HTR6(3362) , HTR7(3363)

Looking for similar products? Visit Product Comparison Guide

General description

Doxepin is used to treat chronic idiopathic urticaria, chronic pain and anxiety. Doxepin exhibits antiserotonergic properties.

Biochem/physiol Actions

Tricyclic antidepressant that is a more potent inhibitor of norepinephrine uptake than of serotonin uptake; antagonist at H1 histamine, muscarinic cholinergic, and α-adrenoreceptors.

Features and Benefits

This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Mixture of cis- and trans-isomers

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Doxepin effects on chronic pain, depression and plasma opioids.
Hameroff SR , et al.
The Journal of Clinical Psychiatry (1982)
J D Moody et al.
Drug metabolism and disposition: the biological fate of chemicals, 27(10), 1157-1164 (1999-09-25)
A filamentous fungus, Cunninghamella elegans ATCC 9245, was used as a microbial model of mammalian metabolism to biotransform doxepin, a tricyclic antidepressant drug. Doxepin is produced as an 85:15% mixture of the trans- (E) and cis- (Z) forms. After 96
E Richelson et al.
The Journal of pharmacology and experimental therapeutics, 230(1), 94-102 (1984-07-01)
Using radioligand binding techniques, we determined the equilibrium dissociation constants (KDS) for a series of antidepressants at the histamine H1, muscarinic acetylcholine, alpha-1 and alpha-2 adrenergic and dopamine (D-2) receptors of normal human brain tissue obtained at autopsy. Twenty-five different
Efficacy of doxepin in the treatment of chronic idiopathic urticaria
Goldsobel AB, et al.
The Journal of Allergy and Clinical Immunology, 78(5), 867-873 (1986)
Y Kitamura et al.
General pharmacology, 27(2), 285-291 (1996-03-01)
To clarify the presence of histamine receptor and its transmembrane mechanism in human T lymphocytes, we investigated the effects of agonists or antagonists of histamine receptor subtypes and bacterial toxins on intracellular concentration of Ca2+ [Ca2+]i), [3H]pyrilamine binding and c-fos
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service