5185. Isometheptene

Nomenclature

CAS number: 503-01-5
N,6-Dimethyl-5-hepten-2-amine; N,1,5-trimethyl-4-hexenylamine; 6-methylamino-2-methylheptene; 2-methyl-6-methylamino-2-heptene; methylisooctenylamine; methyloctenylamine; Octin (Knoll); Octon; Octanil.
C9H19N; mol wt 141.25.
C 76.53%, H 13.56%, N 9.92%.

Description and references

Prepn: Klavehn, Wolf, US 2230753; US 2230754 (both 1941 to E. Bilhuber). Toxicity data: Walton et al., J. Pharmacol. Exp. Ther. 92, 214 (1948).

Chemical structure

Properties

Colorless, oily liq; characteristic amine odor. Strong base. Volatile with steam. d 0.795. bp 176-178°; bp7 58-59°. nD15 1.4472. Practically insol in water. Freely sol in alc, ether, acetone, chloroform.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6168-86-1
C9H19N.HCl; mol wt 177.71.
C 60.83%, H 11.34%, N 7.88%, Cl 19.95%.

Properties

Crystals, very hygroscopic, mp 68-69°. Sol in water, alc. LD50 in mice (mg/kg): 17.5 i.v.; 171 s.c. (Walton).

Derivative

Bitartrate (acid tartrate).

Nomenclature

CAS number: 5984-50-9
C13H25NO6; mol wt 291.34.
C 53.59%, H 8.65%, N 4.81%, O 32.95%.

Properties

Crystals, mp 78-80° (preliminary sintering). Freely sol in water, alcohol.

Derivative

Mucate.

Nomenclature

CAS number: 7492-31-1
C24H48N2O8; mol wt 492.65.
C 58.51%, H 9.82%, N 5.69%, O 25.98%.

Properties

Bitter crystals, mp 152° (rapid heating). Freely sol in water. Soly in alc about 5 g/100 ml. Almost insol in ether, chloroform. LD50 orally in dogs: 148 mg/kg (Walton).

Therapeutic Category

Adrenergic.

Therapeutic Category (Veterinary)

Sympathomimetic. Antispasmodic for gut and urinary tract.

Keywords

α-Adrenergic Agonist