Tripelennamine
Title: Tripelennamine
CAS Registry Number: 91-81-6
CAS Name: N,N-Dimethyl-N¢-(phenylmethyl)-N¢-2-pyridinyl-1,2-ethanediamine
Additional Names: 2-[benzyl(2-dimethylaminoethyl)amino]pyridine; N-benzyl-N¢,N¢-dimethyl-N-(2-pyridyl)ethylenediamine; N,N-dimethyl-N¢-benzyl-N¢-(a-pyridyl)ethylenediamine; b-dimethylaminoethyl-2-pyridylbenzylamine; b-dimethylaminoethyl-2-pyridylaminotoluene
Molecular Formula: C16H21N3
Molecular Weight: 255.36
Percent Composition: C 75.26%, H 8.29%, N 16.46%
Literature 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 Rhône-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).
Properties: Yellow oil. Amine odor. bp0.1 138-142°, bp1.7 185-190°, bp20 193-205°. nD25 1.5759-1.5765. Miscible with water.
Boiling point: bp0.1 138-142°; bp1.7 185-190°; bp20 193-205°
Index of refraction: nD25 1.5759-1.5765
 
Derivative Type: Hydrochloride
CAS Registry Number: 154-69-8
Trademarks: Dehistin (EGYT); Azaron (Chefaro); Pyribenzamine (Novartis); PBZ (Novartis); Vetibenzamina (Novartis)
Molecular Formula: C16H21N3.HCl
Molecular Weight: 291.82
Percent Composition: 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 (e 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).
Melting point: mp 192-193°
Absorption maximum: uv max (water): 244, 305 (e 14470, 4780)
Toxicity data: LD50 in mice (mg/kg): 47 i.p. (Walker)
 
Derivative Type: Citrate
CAS Registry Number: 6138-56-3
Molecular Formula: C16H21N3.C6H8O7
Molecular Weight: 447.48
Percent Composition: 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.
Melting point: mp 106-110°
 
Therap-Cat: Antihistaminic.
Therap-Cat-Vet: Antihistaminic.
Keywords: Antihistaminic; Ethylenediamine Derivatives.

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