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Lefetamine

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Chemical compound
Pharmaceutical compound
Lefetamine
Clinical data
Routes of
administration 		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • (1R)-N,N-dimethyl-1,2-diphenylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H19N
Molar mass 225.335g·mol−1
3D model (JSmol)
  • CN([C@@H](C1=CC=CC=C1)CC2=CC=CC=C2)C
  • InChI=1S/C16H19N/c1-17(2)16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14/h3-12,16H,13H2,1-2H3/t16-/m1/s1[画像:check]Y
  • Key:YEJZJVJJPVZXGX-MRXNPFEDSA-N[画像:check]Y
[画像:X mark]N[画像:check]Y(what is this?) (verify)

Lefetamine (Santenol) is a drug which is a stimulant and also an analgesic with effects comparable to codeine.

Discovery

The parent structure of lefetamine, 1,2-diphenylethylamine was first synthesized in the 1940s and showed weak analgesic activity.[2]

Lefetamine itself was first investigated in Japan in the 1950s.[3] The L-isomer showed weak analgesic action comparable to codeine and antitussive action far weaker than codeine. The d-isomer showed no such activity but caused seizures in rats.[4] [5]

Society and culture

It was abused in Japan during the 1950s. In a small study in 1989 it showed some effect against opioid withdrawal symptoms without causing withdrawal symptoms itself. It was concluded that it may be an opioid partial agonist.[6]

It has been abused in Europe; in 1989 a small study of 15 abusers and some volunteers found that it had some partial similarity to opioids, that it produced withdrawal symptoms, and had dependence and abuse potential to a certain degree.[7]

In a small study in 1994, it was compared to clonidine and buprenorphine in the detoxification of methadone patients and found to be inferior to both of them.[8]

Regulation may vary; it does not appear as either a narcotic or non-narcotic under the US Controlled Substances Act 1970[9]

The Canadian Controlled Drugs and Substances Act was amended in 2016 to include the substance as a Schedule III substance. Possession without legal authority can result in maximum 3 years imprisonment. Further, Health Canada amended the Food and Drug Regulations in May, 2016 to classify Lefetamine as a controlled drug.[10]

Research

Some related pyrrylphenylethanones had analgesic activity comparable to morphine.[11] Some pyrrole analogues were reported to have analgesic effects comparable to lefetamine and being devoid of neurotoxic properties.[12]

See also

References

  1. ↑ Anvisa (2023年03月31日). "RDC No 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023年04月04日). Archived from the original on 2023年08月03日. Retrieved 2023年08月16日.
  2. ↑ Dodds EC, Lawson W, Simpson SA, Williams PC (June 1945). "Testing diphenylethylamine compounds for analgesic action". The Journal of Physiology. 104 (1): 47–51. doi:10.1113/jphysiol.1945.sp004105. PMC 1393527 . PMID 16991666.
  3. ↑ DE patent 1159958, Ogyu K, Fujimura H, Yamakawa Y, Mita I, "Verfahren zur Herstellung von antitussiv wirksamem l-1,2-Diphenyl-1-dimethylaminoaethan und dessen Salzen", issued 1963年12月27日, assigned to Institut Seikatsu Kagaku Kenkyusho (Scientific Research Institute for Practical Life, Kyoto)
  4. ↑ Fujimura H, Kawai K (1961). "Pharmacological Studies on Diphenylalkylamine Derivatives. (I)" (PDF). Bulletin of the Institute for Chemical Research, Kyoto University. 39 (1): 67–77. Archived (PDF) from the original on 2012年05月01日. Retrieved 2011年09月25日.
  5. ↑ Fujimura H, Kawai K, Ohata K, Shibata S (1961). "Pharmacological Studies on Diphenylalkylamine Derivatives. (II): On the Actions of l-1,2-Diphenyl-1-dimethylaminoethane Hydrochloride (SPA)" (PDF). Bulletin of the Institute for Chemical Research, Kyoto University. 39 (1): 78–94. Archived (PDF) from the original on 2016年03月04日. Retrieved 2012年06月30日.
  6. ↑ Mannelli P, Janiri L, De Marinis M, Tempesta E (October 1989). "Lefetamine: new abuse of an old drug--clinical evaluation of opioid activity". Drug and Alcohol Dependence. 24 (2): 95–101. doi:10.1016/0376-8716(89)90071-9. PMID 2571492.
  7. ↑ Janiri L, Mannelli P, Pirrongelli C, Lo Monaco M, Tempesta E (January 1989). "Lephetamine abuse and dependence: clinical effects and withdrawal syndrome". British Journal of Addiction. 84 (1): 89–95. doi:10.1111/j.1360-0443.1989.tb00555.x. PMID 2917208.
  8. ↑ Janiri L, Mannelli P, Persico AM, Serretti A, Tempesta E (October 1994). "Opiate detoxification of methadone maintenance patients using lefetamine, clonidine and buprenorphine". Drug and Alcohol Dependence. 36 (2): 139–45. doi:10.1016/0376-8716(94)90096-5. hdl:11380/1250879 . PMID 7851281.
  9. ↑ "DEA Diversion Control Division". Archived from the original on 2016年03月02日. Retrieved 2016年02月27日.
  10. ↑ "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)". June 2016. Archived from the original on 2017年12月02日. Retrieved 2016年11月17日.
  11. ↑ Massa S, Di Santo R, Mai A, Artico M, Pantaleoni GC, Giorgi R, Coppolino MF (July 1992). "Pyrrylphenylethanones related to cathinone and lefetamine: synthesis and pharmacological activities". Archiv der Pharmazie. 325 (7): 403–9. doi:10.1002/ardp.19923250707. PMID 1417455. S2CID 22300931.
  12. ↑ Massa S, Stefancich G, Artico M, Corelli F, Silvestri R, Pantaleoni GC, et al. (September 1989). "Synthesis, neuropsychopharmacological effects and analgesic-antiinflammatory activities of pyrrole analogues of lefetamine". Farmaco. 44 (9). Societa Chimica Italiana: 763–77. PMID 2604832.

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