5852. Mephentermine

Nomenclature

CAS number: 100-92-5
N,α,α-Trimethylbenzeneethanamine; 2-methylamino-2-methyl-1-phenylpropane; N-methyl-ω-phenyl-tert-butylamine; N,α,α-trimethylphenethylamine.
C11H17N; mol wt 163.26.
C 80.92%, H 10.50%, N 8.58%.

Description and references

α-Adrenergic agonist. Prepd by hydrogenating 1-chloro-2-methylamino-2-methyl-1-phenylpropane hydrochloride in methanol in the presence of palladium barium carbonate: Bruce, Szabo, US 2597445 (1952 to Wyeth). Alternate process: Abel et al., US 2590079 (1952 to Wyeth). Pharmacology: D. K. Eckfeld et al., J. Am. Pharm. Assoc. 43, 705 (1954).

Chemical structure

Properties

Liquid. Fishy amine odor. bp7mm 82-83°. n20D 1.5110. d2020 0.9231. pKa (30°) 10.35. Alkaline reaction. Freely sol in alc. Sol in ether. Practically insol in water.

Derivative

Sulfate dihydrate.

Nomenclature

CAS number: 6190-60-9
Wyamine (Wyeth); Mephine.
(C11H17N)2.H2SO4.2H2O; mol wt 460.63.
C 57.36%, H 8.75%, N 6.08%, S 6.96%, O 20.84%.

Properties

Crystals, mp 215-217° (dec). One gram dissolves in 20 ml water, about 150 ml ethanol (95%). Practically insol in chloroform. pH of aq soln about 6. LD50 (calc as base) intra-abdominally in mice: 89.4 mg/kg (Eckfeld).

Therapeutic Category

Antihypotensive.

Keywords

α-Adrenergic Agonist