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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

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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)

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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’.

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Doxepin effects on chronic pain, depression and plasma opioids.
Hameroff SR , et al.
The Journal of Clinical Psychiatry (1982)
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)
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
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
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
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