5959. Methapyrilene

Nomenclature

CAS number: 91-80-5
N,N-Dimethyl-N′-2-pyridinyl-N′-(2-thienylmethyl)-1,2-ethanediamine; 2-[(2-dimethylaminoethyl)-2-thenylamino]pyridine; N,N-dimethyl-N′-(2-pyridyl)-N′-(2-thenyl)ethylenediamine; N,N-dimethyl-N′-(α-pyridyl)-N′-(2-methylthienyl)ethylenediamine; thenylpyramine; AH-42; Thenylene (Abbott); Pyrathyn (Flint); Thionylan; Histadyl (formerly) (Lilly); Restryl; Rest-On; Sleepwell; Paradormalene; Pyrinistab; Pyrinistol; Lullamin (Reed & Carnrick).
C14H19N3S; mol wt 261.39.
C 64.33%, H 7.33%, N 16.08%, S 12.27%.

Description and references

Prepd by heating a 2-thenyl halide with an alkali metal salt of N,N-dimethyl-N′-(2-pyridyl)ethylenediamine: Kyrides, US 2581868 (1952 to Monsanto). Alternate syntheses: Weston, J. Am. Chem. Soc. 69, 980 (1947); Clapp et al., ibid. 1549. Toxicity data: H. M. Lee et al., Proc. Soc. Exp. Biol. Med. 80, 458 (1952). Carcinogenicity study: W. Lijinsky et al., Science 209, 817 (1980). Study of mechanism of hepatocarcinogenicity: K. L. Steinmetz et al., Carcinogenesis 9, 959 (1988). Clinical pharmacokinetics: E. P. Calandre et al., Clin. Pharmacol. Ther. 29, 527 (1981). HPLC determn in feed and sleep aid tablets: B. Shaikh, M. R. Hallmark, J. Assoc. Off. Anal. Chem. 64, 889 (1981); in feed, urine and wastewater: H. C. Thompson, Jr., C. L. Holder, J. Chromatogr. 283, 251 (1984).

Chemical structure

Properties

Liquid. bp0.45 125-135°; bp3 173-175°. nD25 1.5842 (also reported as 1.5835). LD50 in mice, guinea pigs (mg/kg): 182.2 ±12.8, 374.9 ±34.5 orally; in mice (mg/kg): 19.85 ±0.69 i.v. (Lee).

Derivative

Hydrochloride.

Nomenclature

CAS number: 135-23-9
C14H19N3S.HCl; mol wt 297.85.
C 56.45%, H 6.77%, N 14.11%, S 10.77%, Cl 11.90%.

Properties

Bitter crystals, mp 162°. uv max: 238 nm (E1%1cm 623); min: 272 nm. One gram dissolves in about 0.5 ml water, in 5 ml alcohol, in 3 ml chloroform. Practically insol in ether, benzene.

Derivative

Fumarate.

Nomenclature

CAS number: 33032-12-1
(C14H19N3S)2.3C4H4O4; mol wt 870.99.
C 55.16%, H 5.79%, N 9.65%, S 7.36%, O 22.04%.

Description and references

Prepn: Meyer, GB 694805 (1953 to Monsanto).

Properties

Crystals, mp 135-136°.

Therapeutic Category

Antihistaminic.

Therapeutic Category (Veterinary)

Antihistaminic.

Keywords

Antihistaminic; Ethylenediamine Derivatives