Diphenhydramine
Title: Diphenhydramine
CAS Registry Number: 58-73-1
CAS Name: 2-Diphenylmethoxy-N,N-dimethylethanamine
Additional Names: 2-(benzhydryloxy)-N,N-dimethylethylamine; b-dimethylaminoethyl benzhydryl ether; O-benzhydryldimethylaminoethanol; b-dimethylaminoethanol diphenylmethyl ether; a-(2-dimethylaminoethoxy)diphenylmethane; benzhydramine
Molecular Formula: C17H21NO
Molecular Weight: 255.35
Percent Composition: C 79.96%, H 8.29%, N 5.49%, O 6.27%
Literature References: Prepn: G. Rieveschl, Jr., US 2421714 (1947 to Parke, Davis); see also H. Martin et al., US 2397799 (1946 to Geigy). Toxicology study: O. M. Gruhzit, R. A. Fisken, J. Pharmacol. Exp. Ther. 89, 227 (1947). Comprehensive description of the hydrochloride: I. J. Holcomb, S. A. Fusari, Anal. Profiles Drug Subs. 3, 173-232 (1974). Clinical pharmacokinetics: J. M. Scavone et al., J. Clin. Pharmacol. 38, 603 (1998). Clinical trial in insomnia: K. Rickels et al., ibid. 23, 235 (1983).
Properties: bp2.0 150-165°.
Boiling point: bp2.0 150-165°
 
Derivative Type: Hydrochloride
CAS Registry Number: 147-24-0
Trademarks: Allergina (Boehringer, Ing.); Benadryl (Pfizer); Benocten (Medinova); Dibondrin (Montavit); Dolestan (Krewel); Halbmond (Wyeth); Noctomin (Medichemie); Nytol (GSK); Sedopretten (Schoening); Sekundal-D (Aventis); Sominex (GSK); Unisom Sleepgels (Pfizer)
Molecular Formula: C17H21NO.HCl
Molecular Weight: 291.82
Percent Composition: C 69.97%, H 7.60%, N 4.80%, O 5.48%, Cl 12.15%
Properties: Crystals from abs alcohol + ether, mp 166-170°. Bitter taste. Slowly darkens on exposure to light. Stable under ordinary conditions. One gram dissolves in 1 ml water, 2 ml alcohol, 2 ml chloroform, 50 ml acetone. Very slightly sol in benzene, ether. pH of 1% aq soln about 5.5. The aq soln forms a pink precipitate with satd Reinecke's salt soln. LD50 orally in rats: 500 mg/kg (Gruhzit, Fisken).
Melting point: mp 166-170°
Toxicity data: LD50 orally in rats: 500 mg/kg (Gruhzit, Fisken)
 
Therap-Cat: Antihistaminic; sedative, hypnotic.
Therap-Cat-Vet: Antihistaminic. Also in motion sickness.
Keywords: Antihistaminic; Aminoalkylethers; Sedative/Hypnotic.

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