1186. Bethanidine

Nomenclature

CAS number: 55-73-2
N,N′-Dimethyl-N″-(phenylmethyl)guanidine; 1-benzyl-2,3-dimethylguanidine; N-benzyl-N′,N″-dimethylguanidine.
C10H15N3; mol wt 177.25.
C 67.76%, H 8.53%, N 23.71%.

Description and references

Adrenergic neuron blocking agent. Prepn: Walton, Ruffell, US 3168562 (1965 to Wellcome Found.); GB 1084461 and GB 1111564 (1967 and 1968 to Wellcome Found.). Pharmacology: A. L. A. Boura, A. F. Green, Br. J. Pharmacol. 20, 36 (1963); J. A. Oates et al., Ann. N.Y. Acad. Sci. 179, 302 (1971). Pharmacokinetics: C. N. Corder, J. Clin. Pharmacol. 19, 428 (1979). HPLC determn in plasma: J. R. Shipe et al., Clin. Chem. 29, 1793 (1983). Anti-arrhythmic activity: M. B. Bacaner, D. G. Benditt, Am. J. Cardiol. 50, 728 (1982); J. C. Somberg et al., ibid. 54, 343 (1984). Review: A. F. Green, Br. J. Clin. Pharmacol. 13, 25-34 (1982).

Chemical structure

Properties

Crystals from methanol + ether, mp 195-197°.

Derivative

Hydriodide.
C10H15N3.HI; mol wt 305.16.
C 39.36%, H 5.28%, N 13.77%, I 41.59%.

Properties

Crystals from ethanol + ether, mp 141-146°.

Derivative

Sulfate.

Nomenclature

CAS number: 114-85-2
Benzaidin; BW-467C60; Bendogen (Lagap); Benzoxine (Sanwa); Betaling (Tanabe); Betanidol (Tanabe Seiyaku); Esbatal (Burroughs Wellcome); Eusmanid; Hypersin (Zeria); Tenathan (Robins).
(C10H15N3)2.H2SO4; mol wt 452.57.
C 53.08%, H 7.13%, N 18.57%, S 7.09%, O 14.14%.

Properties

LD50 in mice (mg/kg): 12 i.v.; 150 i.p.; 260 s.c.; 520 by stomach intubation (Boura, Green).

Therapeutic Category

Antihypertensive.

Keywords

Antihypertensive; Guanidine Derivatives