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Merck
CN

D4526

Doxepin hydrochloride

≥98% (GC), norepinephrine uptake inhibitor, 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
NACRES:
NA.77
PubChem Substance ID:
24278093
UNSPSC Code:
12352200
EC Number:
214-966-8
MDL number:
MFCD00079135

Key Documents

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Product Name

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

InChI key

MHNSPTUQQIYJOT-SJDTYFKWSA-N

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+;

SMILES string

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

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

Quality Level

200

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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Related Categories

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.

General description

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

Other Notes

Mixture of cis- and trans-isomers

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV8169
MKCQ8694
MKCQ5167
MKCM2122
MKCK0760

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