3441. Doxylamine

Nomenclature

CAS number: 469-21-6
N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine; 2-[α-(2-dimethylaminoethoxy)-α-methylbenzyl]pyridine; phenyl-2-pyridylmethyl-β-N,N-dimethylaminoethyl ether; 2-dimethylaminoethoxyphenylmethyl-2-picoline.
C17H22N2O; mol wt 270.37.
C 75.52%, H 8.20%, N 10.36%, O 5.92%.

Description and references

Prepn: C. H. Tilford et al., J. Am. Chem. Soc. 70, 4001 (1948); N. Sperber et al., ibid. 71, 887 (1949). Pharmacology: B. B. Brown, H. Werner, J. Lab. Clin. Med. 33, 325 (1948). GC determn: H. C. Thompson et al., J. Chromatogr. Sci. 20, 373 (1982). Chronic toxicity study: C. D. Jackson, B. Blackwell, J. Am. Coll. Toxicol. 12, 1 (1993). Review of properties and pharmacology: T. J. Haley, Dangerous Prop. Ind. Mater. Rep. 2, 17-20 (1982). Clinical evaluation as hypnotic: F. Sj"oqvist, L. Lasagna, Clin. Pharmacol. Ther. 8, 48 (1967); as antihistaminic for use in colds: R. Eccles et al., J. Pharm. Pharmacol. 47, 990 (1995).

Chemical structure

Properties

Liquid, bp0.5 137-141°. Sol in acids. Slightly volatile, darkens on exposure to light.

Derivative

Succinate.

Nomenclature

CAS number: 562-10-7
Gittalun (Boehringer, Ing.); Hoggar (Stada); Mereprine (Cassella-med); Sedaplus (Rosen Pharma); Unisom (Pfizer).
C17H22N2O.C4H6O4; mol wt 388.46.
C 64.93%, H 7.27%, N 7.21%, O 20.59%.

Properties

Crystals, mp 100-104°, sol in water. One gram dissolves in 1 ml water, 2 ml alcohol, 2 ml chloroform. Slightly sol in benzene and ether. pH (1% aq soln): 4.9 to 5.1. LD50 in mice, rabbits (mg/kg): 470, 250 orally; 62, 49 i.v.; in mice, male rats, female rats (mg/kg): 460, 440, 445 s.c. (Brown, Werner).

Derivative

Combination with pyridoxine hydrochloride.

Nomenclature

Bendectin (Duchesnay); Diclectin (Duchesnay).

Description and references

Has been used for nausea of pregnancy. Some formulations also contained dicyclomine, q.v. Review of therapeutic use and the issue of teratogenicity: L. J. Sheffield, R. Batagol, Med. J. Aust. 143, 143-147 (1985); R. L. Brent, Reprod. Toxicol. 9, 337-349 (1995).

Therapeutic Category

Antihistaminic; sedative, hypnotic.

Therapeutic Category (Veterinary)

Antihistaminic.

Keywords

Antihistaminic; Aminoalkylethers; Sedative/Hypnotic