1906. Cathinone

Nomenclature

CAS number: 71031-15-7
(2S)-2-Amino-1-phenyl-1-propanone; (-)-α-aminopropiophenone; norephedrone.
C9H11NO; mol wt 149.19.
C 72.46%, H 7.43%, N 9.39%, O 10.72%.

Description and references

Psychoactive alkaloid found in the leaves of the khat plant, Catha edulis Forsk., Celastraceae. Prepn of racemic compd: L. Behr-Bergowski, Ber. 30, 1515 (1897); S. Gabriel, ibid. 41, 1127 (1908). Isoln from C. edulis: X. Schorno, E. Streinegger, Experientia 35, 572 (1979); and identification as active constituent of khat: D. W. Peterson et al., Life Sci. 27, 2143 (1980). Stereospecific synthesis from norephedrine: B. D. Berrang et al., J. Org. Chem. 47, 2643 (1982). Metabolism in humans: R. Brenneisen et al., J. Pharm. Pharmacol. 38, 298 (1986). HPLC determn in urine: K. Mathys, R. Brenneisen, J. Chromatogr. 593, 79 (1992). Quantitative determn in khat: A. M. Al-Obaid et al., J. Pharm. Biomed. Anal. 17, 321 (1998). Review of pharmacology: P. Kalix, Pharmacol. Toxicol. 70, 77-86 (1992).

Chemical structure

Properties

Sol in methanol (with racemization), methylene chloride. [α]D -46.8° (c = 0.24 in methanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 76333-53-4
C9H11NO.HCl; mol wt 185.65.
C 58.23%, H 6.52%, N 7.54%, O 8.62%, Cl 19.10%.

Properties

Crystals from isopropanol-THF, mp 189-190°.

Note

This is a controlled substance (stimulant): 21 CFR, 1308.11.