2138. Dibenamine

Nomenclature

CAS number: 51-50-3
N-(2-Chloroethyl)-N-(phenylmethyl)benzenemethanamine; N-(2-Chloroethyl)dibenzylamine; N,N-dibenzyl-β-chloroethylamine; N,N-dibenzylaminoethyl chloride.
C16H18ClN; mol wt 259.77.
C 73.98%, H 6.98%, Cl 13.65%, N 5.39%.

Description and references

α-Adrenergic blocker. Prepn: W. S. Gump, E. J. Nikawitz, J. Am. Chem. Soc. 72, 1309 (1950); T. F. Wood, US 2540155 (1951 to Burton T. Bush, Inc.). Pharmacology and toxicity: M. Nickerson, G. M. Nomaguchi, J. Pharmacol. Exp. Ther. 101, 379 (1951). Use in adrenergic receptor differentiation: R. F. Furchgott, ibid. 111, 265 (1954); in specific receptor labelling: R. D. Green et al., ibid. 187, 524 (1973). In vivo studies of protection against hepatotoxic agents: H. M. Maling et al., Toxicol. Appl. Pharmacol. 27, 380 (1974); E. K. Weisburger et al., ibid. 28, 477 (1974); H. M. Maling et al., Biochem. Pharmacol. 23, 1479 (1974).

Chemical structure

Properties

Yellow oily liquid. bp12 194-195°; bp5 182-184°. nD20 1.5655.

Derivative

Hydrochloride.

Nomenclature

CAS number: 55-43-6
C16H18ClN.HCl; mol wt 296.23.
C 64.87%, H 6.46%, Cl 23.94%, N 4.73%.

Properties

Crystals, mp 192°, also given as 180-181°. Practically insol in water near neutrality. Sol in dil acids (2% at pH 2.1, 1% at pH 2.4 and 0.5% at pH 2.7), in 95% alcohol and in propylene glycol. Stable in acid soln, but rapidly loses activity in neutral or alkaline solns. LD50 s.c. in mice: 800 mg/kg (Nickerson, Nomaguchi).