7316. Phenyltoloxamine

Nomenclature

CAS number: 92-12-6
N,N-Dimethyl-2-[2-(phenylmethyl)phenoxy]ethanamine; N,N-dimethyl-2-(α-phenyl-o-tolyloxy)ethylamine; N,N-dimethyl-2-(α-phenyl-o-toloxy)ethylamine; 2-(2-dimethylaminoethoxy)diphenylmethane; 2-benzhydryl β-dimethylaminoethyl ether; 2-benzylphenyl β-dimethylaminoethyl ether; PRN; bistrimin; C-5581H; Antin; Phenoxadrine.
C17H21NO; mol wt 255.35.
C 79.96%, H 8.29%, N 5.49%, O 6.27%.

Description and references

Prepn: Cheney et al., J. Am. Chem. Soc. 71, 60 (1949); Binkley, Cheney, US 2703324 (1955 to Bristol Labs.).

Chemical structure

Properties

Oily liquid, bp 141-144° (at <0.1 mm Hg).

Derivative

Dihydrogen citrate.
C17H21NO.C6H8O7; mol wt 447.48.
C 61.73%, H 6.53%, N 3.13%, O 28.60%.

Properties

Crystals from water or methanol, mp 138-140°. Soluble in water.

Derivative

Hydrochloride.
C17H21NO.HCl; mol wt 291.82.
C 69.97%, H 7.60%, N 4.80%, O 5.48%, Cl 12.15%.

Properties

Crystals from methyl isobutyl ketone, mp 119-121°. Soluble in water.

Therapeutic Category

Dihydrogen citrate as antihistaminic.

Keywords

Antihistaminic; Aminoalkylethers