9738. Tripelennamine

Nomenclature

CAS number: 91-81-6
N,N-Dimethyl-N′-(phenylmethyl)-N′-2-pyridinyl-1,2-ethanediamine; 2-[benzyl(2-dimethylaminoethyl)amino]pyridine; N-benzyl-N′,N′-dimethyl-N-(2-pyridyl)ethylenediamine; N,N-dimethyl-N′-benzyl-N′-(α-pyridyl)ethylenediamine; β-dimethylaminoethyl-2-pyridylbenzylamine; β-dimethylaminoethyl-2-pyridylaminotoluene.
C16H21N3; mol wt 255.36.
C 75.26%, H 8.29%, N 16.46%.

Description and references

Prepn: C. P. Huttrer et al., J. Am. Chem. Soc. 68, 1999 (1946); C. Djerassi et al., US 2406594 (1946 to Ciba); R. J. Horclois, US 2502151 (1950 to Rhne-Poulenc). Crystal structure: M. Parvez, Acta Crystallogr. C43, 1408 (1987). Toxicity studies: D. P. Waller et al., Clin. Toxicol. 16, 17 (1980). Comprehensive description: H. G. Piskorik, Anal. Profiles Drug Subs. 14, 108-133 (1985).

Chemical structure

Properties

Yellow oil. Amine odor. bp0.1 138-142°, bp1.7 185-190°, bp20 193-205°. nD25 1.5759-1.5765. Miscible with water.

Derivative

Hydrochloride.

Nomenclature

CAS number: 154-69-8
Dehistin (EGYT); Azaron (Chefaro); Pyribenzamine (Novartis); PBZ (Novartis); Vetibenzamina (Novartis).
C16H21N3.HCl; mol wt 291.82.
C 65.85%, H 7.60%, N 14.40%, Cl 12.15%.

Properties

Crystals from ethyl acetate + methanol, mp 192-193°. Bitter taste, produces temporary numbness of the tongue. uv max (water): 244, 305 (ε 14470, 4780). One gram dissolves in 0.77 ml water, in 6 ml alcohol, in 6 ml chloroform, in about 350 ml acetone. Practically insol in benzene, ether, ethyl acetate. About neutral to litmus. pH of aq soln contg 25 mg/ml: 6.71; 50 mg/ml: 6.67; 100 mg/ml: 5.56. LD50 in mice (mg/kg): 47 i.p. (Walker).

Derivative

Citrate.

Nomenclature

CAS number: 6138-56-3
C16H21N3.C6H8O7; mol wt 447.48.
C 59.05%, H 6.53%, N 9.39%, O 25.03%.

Properties

Crystals, mp 106-110°. Less bitter than the hydrochloride. Freely sol in water, alcohol. Very slightly sol in ether. Practically insol in benzene, chloroform. 1% aq soln has a pH of 4.25.

Therapeutic Category

Antihistaminic.

Therapeutic Category (Veterinary)

Antihistaminic.

Keywords

Antihistaminic; Ethylenediamine Derivatives