IUPAC_name = (R)-N,N-dimethyl-1,2-diphenyl-ethanamine

width = 130
CAS_number = 7262-75-1
synonyms = Lefetamine, Santenol, SPA, (-)-N,N-dimethyl-1,2-diphenylethylamine, 1-dimethylamino-1,2-diphenylethane
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C = 16 | H = 19 | N = 1
molecular_weight = 225.329 g/mol
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legal_US = Schedule IV
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Lefetamine (Santenol) is a psychoactive drug which is both a stimulant and an analgesic with effects comparable to both morphine and methylphenidate.

Lefetamine was invented in the 1940s [ Dodds EC, Lawson W, Simpson SA, Williams PC. Testing diphenylethylamine compounds for analgesic action. Journal of Physiology (1945); (104):47-51. ] and was widely abused in Japan [ K. Ogiu et al., J. Pharm. Soc. Japan 80, 283 (1960) ] during the 1950s. [ Mannelli P, Janiri L, De Marinis M, Tempesta E. Lefetamine: new abuse of an old drug--clinical evaluation of opioid activity. Drug and Alcohol Dependence. 1989 Oct;24(2):95-101. ] It has been researched for medicinal use but showed little advantage over other analgesics, although it did seem promising for treating opiate withdrawal it was not as good as buprenorphine for this purpose. [ Janiri L, Mannelli P, Persico AM, Serretti A, Tempesta E. Opiate detoxification of methadone maintenance patients using lefetamine, clonidine and buprenorphine. Drug and Alcohol Dependence. 1994 Oct;36(2):139-45. ] More recently it has been abused in Europe, but it remains an obscure drug on the illicit market.

Due to its chemical structure, it binds to opioid receptors while simultaneously inhibiting reuptake of dopamine and norepinephrine. [ Janiri L, Mannelli P, Pirrongelli C, Lo Monaco M, Tempesta E. Lephetamine abuse and dependence: clinical effects and withdrawal syndrome. British Journal of Addiction. 1989 Jan;84(1):89-95. ] Lefetamine has the necessary tertiary amine functional group required for opioid receptor recognition, as well as a phenethylamine skeleton (which is responsible for its amphetamine-like effects). [ Massa S, Di Santo R, Mai A, Artico M, Pantaleoni GC, Giorgi R, Coppolino MF. Pyrrylphenylethanones related to cathinone and lefetamine: synthesis and pharmacological activities. Archiv der Pharmazie (Weinheim). 1992 Jul;325(7):403-9. ] It is also reported to have some NMDA antagonist effects and to have neurotoxic properties. [ Massa S, Stefancich G, Artico M, Corelli F, Silvestri R, Pantaleoni GC, Fanini D, Palumbo G, Giorgi R. Synthesis, neuropsychopharmacological effects and analgesic-antiinflammatory activities of pyrrole analogues of lefetamine. Farmaco. 1989 Sep;44(9):763-77. ]

Boiling Point: 142-147° C

Optical Rotation: [α] D20 -124.2° (ethanol).

CAS number of hydrochloride: 14148-99-3


ee also

*Opioid receptor

External links

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