5431. Lefetamine

Nomenclature

CAS number: 7262-75-1
(αR)-N,N-Dimethyl-α-phenylbenzeneethanamine; ()-N,N-dimethyl-1,2-diphenylethylamine; ()-N,N-dimethyl-α-phenylphenethylamine.
C16H19N; mol wt 225.33.
C 85.28%, H 8.50%, N 6.22%.

Description and references

Centrally acting analgesic with stereochemical resemblance to morphine, q.v. Prepn and activity: K. Ogiu et al., J. Pharm. Soc. Jpn. 80, 283 (1960); eidem, JP 61 23087 (1961 to Res. Found. Practical Life). Absolute configuration: M. Nakazaki, Chem. Ind. (London) 1962, 1577. NMR data indicates 22% eclipsed conformation which appears to enhance stereoselectivity for morphine receptors: T. Sasaki et al., J. Med. Chem. 9, 847 (1966). Pharmacology: H. Nakamura, M. Shimizu, Arch. Int. Pharmacodyn. Ther. 221, 105 (1976). Clinical study: J. P. Famaey, T. L. Peeters, Brux. Med. 56, 21 (1976). Analgesic activity: M. Nozaki et al., Life Sci. 33, Suppl. 1, 431 (1983). Opiate agonist activity: M. Graziella de Montis et al., Pharmacol. Res. Commun. 17, 471 (1985).

Chemical structure

Properties

bp6 142-147°. [α]D20 124.2° (ethanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 14148-99-3
C16H19N.HCl; mol wt 261.79.
C 73.41%, H 7.70%, N 5.35%, Cl 13.54%.

Properties

mp 218-219°. [α]D20 91.7° (water).

Note

This is a controlled substance (stimulant): 21 CFR, 1308.14.

Therapeutic Category

Analgesic.