Structural Formula Vector Image
Title: Amphetamine
CAS Registry Number: 300-62-9
CAS Name: a-Methylbenzeneethanamine
Additional Names: (±)-a-methylphenethylamine; 1-phenyl-2-aminopropane; b-phenylisopropylamine; b-aminopropylbenzene; (±)-desoxynorephedrine
Molecular Formula: C9H13N
Molecular Weight: 135.21
Percent Composition: C 79.95%, H 9.69%, N 10.36%
Literature 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).
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).
Boiling point: bp760 200-203°; bp13 82-85°
Density: d425 0.913
Toxicity data: LD50 in rats (mg/kg): 180 s.c. (Warren, Werner)
Derivative Type: Sulfate
CAS Registry Number: 60-13-9
Trademarks: Benzedrine (SKB)
Molecular Formula: (C9H13N)2.H2SO4
Molecular Weight: 368.49
Percent Composition: 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). 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).
Melting point: mp above 300° (dec)
Toxicity data: LD50 in mice, rats (mg/kg): 24.2, 55 orally (Behrendt, Deininger)
Derivative Type: Phosphate
CAS Registry Number: 139-10-6
Trademarks: Actemin (Lazar); Aktedron (Chinoin)
Molecular Formula: C9H13N.H3PO4
Molecular Weight: 233.20
Percent Composition: C 46.35%, H 6.92%, N 6.01%, P 13.28%, O 27.44%
Literature 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 Type: d-Form see Dextroamphetamine
Derivative Type: l-Form
CAS Registry Number: 156-34-3
Additional Names: Levamphetamine; levamfetamine
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.12.
Therap-Cat: CNS stimulant; anorexic.
Keywords: Anorexic; CNS Stimulant.

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