DOXYLAMINE Chemical Properties

Melting point:

25°C

Boiling point:

bp0.5 137-141°

Density 

1.0023 (rough estimate)

refractive index 

1.5486 (estimate)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Oil

pka

pKa 9.20(H2O t = 25 c = 0.002–0.01) (Uncertain);4.4 (Uncertain);9.2 (Uncertain)

color 

Colourless

Stability:

Temperature Sensitive

EPA Substance Registry System

Doxylamine (469-21-6)

Safety Information

Hazardous Substances Data

469-21-6(Hazardous Substances Data)

Toxicity

An antihistamine that formerly was used in pregnant women for antihistaminic and sedative properties. Although it has excellent sedative properties, it has been implicated in teratogenesis and in causing neurobehavioral toxicity and is therefore no longer used

DOXYLAMINE Usage And Synthesis

Uses

Antihistaminic.

Uses

(±)-Doxylamine is an intermediate in the synthesis of Doxylamine N, N’-Dioxide (D562025), which is an impurity of Doxylamine (succinate salt, D562000), which is an H1 Histamine receptor antagonist.

Definition

ChEBI: Doxylamine is a member of pyridines and a tertiary amine. It has a role as a histamine antagonist, a cholinergic antagonist, a sedative, an antiemetic, a H1-receptor antagonist, an anti-allergic agent and an antitussive.

brand name

Decapryn (Sanofi Aventis); Unisom (Pfizer).

General Description

Clear colorless liquid.

Reactivity Profile

DOXYLAMINE is an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides

Synthesis

Doxylamine is synthesized from phenyl-2- pyridinylmethyl carbinol and dimethylaminoethyl chloride in the presence of NaNH2 in xylene . It exhibits pronounced sedative effects. Therefore, doxylamine is mainly used as a sedative, a sleeping aid.

DOXYLAMINE(469-21-6)Related Product Information

• Tamsulosin
• DOXYLAMINE HYDROGEN SUCCINATE
• DOXYLAMINE HYDROGEN SUCCINATE IMP. D (EP): PHENYL(PYRIDIN-2-YL)METHANONE(2-BENZOYLPYRIDINE)
• DOXYLAMINE IMPURITY A
• DOXYLAMINE HYDROGEN SUCCINATE - REFERENCE SPECTRUM
• 2-(alpha-(beta-Dimethylaminoethoxy)-alpha-methyl-3,4-dimethylbenzyl)py ridine hydrochloride
• Doxylamine-d5
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• DOXYLAMINE SUCCINATE,DOXYLAMINE SUCCINATE SALT
• DOXYLAMINE