582. Amphetamine

Nomenclature

CAS number: 300-62-9
α-Methylbenzeneethanamine; (±)-α-methylphenethylamine; 1-phenyl-2-aminopropane; β-phenylisopropylamine; β-aminopropylbenzene; (±)-desoxynorephedrine.
C9H13N; mol wt 135.21.
C 79.95%, H 9.69%, N 10.36%.

Description and references

Prepn: L. Edeleano, Ber. 20, 616 (1887); F. P. Nabenhauer, US 1921424 (1933 to SK & F); W. H. Hartung, J. C. Munch, J. Am. Chem. Soc. 53, 1875 (1931); N. Kornblum, D. C. Iffland, ibid. 71, 2137 (1949). Demonstration of binding sites in hypothalamic membranes: S. M. Paul et al., Science 218, 487 (1982). Toxicity data: M. R. Warren, H. W. Werner, J. Pharmacol. Exp. Ther. 85, 119 (1945); W. A. Behrendt, R. Deininger, Arzneim.-Forsch. 13, 711 (1963). Books: C. D. Leake, The Amphetamines: Their Actions and Uses (Thomas, Springfield, 1958) 167 pp; O. J. Kalant, The Amphetamines: Toxicity and Addiction (Thomas, Springfield, 1966) 151 pp. Review of use and abuse: J. P. Morgan, Substance Abuse: Clinical Problems and Perspectives, J. H. Lowinson, P. Ruiz, Eds. (Williams & Wilkins, Baltimore, 1981) pp 167-184. Review of pharmacology, behavioral effects and therapeutic uses: L. S. Seiden et al., Annu. Rev. Pharmacol. Toxicol. 32, 639-677 (1993). Review of HPLC determns in biological samples: P. Campins-Falco et al., J. Liq. Chromatogr. 17, 731-747 (1994).

Chemical structure

Properties

Mobile liquid. Amine odor. Acrid, burning taste. Volatilizes slowly at room temp. d425 0.913. bp760 200-203°; bp13 82-85°. Slightly soluble in water; sol in alc, ether; readily sol in acids. Aq solns are alkaline to litmus. LD50 in rats (mg/kg): 180 s.c. (Warren, Werner).

Derivative

Sulfate.

Nomenclature

CAS number: 60-13-9
Benzedrine (SKB).
(C9H13N)2.H2SO4; mol wt 368.49.
C 58.67%, H 7.66%, N 7.60%, S 8.70%, O 17.37%.

Properties

White, odorless crystalline powder with slightly bitter taste. mp above 300° (dec). Freely sol in water (1:9); slightly sol in alcohol (about 1:500). Practically insol in ether. A soln of 1 g/10 ml water has a pH 5-6. LD50 in mice, rats (mg/kg): 24.2, 55 orally (Behrendt, Deininger).

Derivative

Phosphate.

Nomenclature

CAS number: 139-10-6
Actemin (Lazar); Aktedron (Chinoin).
C9H13N.H3PO4; mol wt 233.20.
C 46.35%, H 6.92%, N 6.01%, P 13.28%, O 27.44%.

Description and references

Prepn: Goggin, US 2507468 (1950 to Clark & Clark).

Properties

Crystals bitter taste. Sinters at about 150°. Dec around 300°. Freely sol in water. Slightly sol in alcohol. Practically insol in benzene, chloroform, ether. The pH of a 10% soln is about 4.6.

Derivative

d-Form see Dextroamphetamine.

Derivative

l-Form.

Nomenclature

CAS number: 156-34-3
Levamphetamine; levamfetamine.

Note

This is a controlled substance (stimulant): 21 CFR, 1308.12.

Therapeutic Category

CNS stimulant; anorexic.

Keywords

Anorexic; CNS Stimulant