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.
