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469-21-6

469-21-6 Structure

469-21-6 Structure
IdentificationBack Directory
[Name]

DOXYLAMINE
[CAS]

469-21-6
[Synonyms]

oxylamine
NCI C60684
DOXYLAMINE
DOXYLAMINE USP/EP/BP
Doxylamine Hydrogen inate
2-dimethylaminoethoxyphenylmethyl-2-picoline
alpha-Dimethylaminoethoxyphenylmethyl-2-picoline
dimethyl(2-(1-phenyl-1-(2-pyridyl)ethoxy)ethyl)amine
2-[a-(2-dimethylaminoethoxy)-a-methylbenzyl]pyridine
phenyl-2-pyridylmethyl-b-N,N-dimethylaminoethyl ether
Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether
N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine
Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-
2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine
Pyridine, 2-[alpha-[2-(dimethylamino)ethoxy]-alpha-methylbenzyl]-
[EINECS(EC#)]

207-414-2
[Molecular Formula]

C17H22N2O
[MDL Number]

MFCD00599469
[MOL File]

469-21-6.mol
[Molecular Weight]

270.37
Chemical PropertiesBack Directory
[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 DataBack Directory
[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
Hazard InformationBack Directory
[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.
[Uses]

Antihistaminic.
[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.
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