D3775

Sigma-Aldrich

Doxylamine succinate salt

Empirical Formula (Hill Notation):
C17H22N2O · C4H6O4
CAS Number:
Molecular Weight:
388.46
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

originator

Sanofi Aventis

SMILES string

OC(=O)CCC(O)=O.CN(C)CCOC(C)(c1ccccc1)c2ccccn2

InChI

1S/C17H22N2O.C4H6O4/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16;5-3(6)1-2-4(7)8/h4-12H,13-14H2,1-3H3;1-2H2,(H,5,6)(H,7,8)

InChI key

KBAUFVUYFNWQFM-UHFFFAOYSA-N

Gene Information

human ... HRH1(3269)

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General description

Doxylamine belongs to the ethanolaime class of antihistamines and is metabolized by the liver into N-demethyl doxylamine and N,N-didemethyl doxylamine. It is generally available as an over the counter (OTC) drug for allergy and cold symptoms.

Application

Doxylamine succinate salt has been used as a therapeutic drug to check developmental toxicity.
Doxylamine succinate salt has been used to study the effects of non-teratogenic exposures on morphology and gene expression in human embryonic stem cell aggregates (HESCA)-CSR, under low concentration of retinoic acid in CS medium.

Packaging

5, 50 g in glass bottle

Biochem/physiol Actions

H1 histamine receptor antagonist; hypnotic.
Doxylamine suppresses histamine at the H1 receptor. It is associated with the short term management of insomnia and temporary relief of common cold symptoms. On the other hand, doxylamine intoxication is linked with rhabdomyolysis and secondary acute renal failure.
Studies in mice show that doxylamine induces liver microsomal cytochrome P450 and other enzymes involved in thyroxine (T4) metabolism. In combination with pyridoxine hydrochloride, this drug is used to treat morning sickness.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Certificate of Analysis

Certificate of Origin

Husnain Syed et al.
BMJ case reports, 2009, doi:10-doi:10 (2009-01-01)
The present report highlights the possible adverse effects of doxylamine, a common over the counter sleep aid. Doxylamine is an antihistamine that at toxic doses can cause anticholinergic effects, including seizures, rhabdomyolysis and death. The following case describes a patient...
D V Gauvin et al.
European journal of pharmacology, 294(1), 281-288 (1995-12-27)
Rats were trained to discriminate between 10 mg/kg cocaine and saline injections under a fixed ratio 10 schedule of food-motivated lever press responding. Once stimulus control was achieved, reinforced test sessions were conducted to assess the degree of generalization of...
L F Soto et al.
Postgraduate medicine, 93(8), 227-229 (1993-06-01)
Clinicians should be aware of the complications of rhabdomyolysis in patients who ingest doxylamine succinate and other over-the-counter antihistamines. The easy availability of these substances increases the potential not only for intentional overdose by adults but also for inadvertent ingestion...
Sebastián Videla et al.
Drugs in R&D, 12(4), 217-225 (2012-12-13)
Doxylamine succinate, an ethanolamine-based antihistamine, is used in the short-term management of insomnia because of its sedative effects. The data available on the pharmacokinetic profile of doxylamine in humans are limited, notwithstanding that this drug has been marketed in European...
Ashutosh Pathak et al.
Journal of AOAC International, 91(5), 1059-1069 (2008-11-05)
Three simple, rapid, and accurate methods, i.e., the derivative ratio spectra-zero-crossing method (method I), double divisor-ratio spectra derivative method (method II), and column reversed-phase high-performance liquid chromatographic (RP-HPLC) method (method III) were developed for the simultaneous determination of doxylamine succinate...

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