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Lefetamine

From Wikipedia, the free encyclopedia
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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC16H19N
Molar mass225.335 g·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 checkY
  • Key:YEJZJVJJPVZXGX-MRXNPFEDSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lefetamine (Santenol) is adrug which is astimulant and also ananalgesic with effects comparable tocodeine.

Discovery

[edit]

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

Lefetamine itself was first investigated inJapan 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

[edit]

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 inEurope; 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 toclonidine andbuprenorphine in the detoxification ofmethadone patients and found to be inferior to both of them.[8]

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

The CanadianControlled 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 theFood and Drug Regulations in May, 2016 to classify Lefetamine as a controlled drug.[10]

Research

[edit]

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

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-03-31)."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 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  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 wirksameml-1,2-Diphenyl-1-dimethylaminoaethan und dessen Salzen", issued 1963-12-27, 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 2012-05-01. Retrieved2011-09-25.
  5. ^Fujimura H, Kawai K, Ohata K, Shibata S (1961)."Pharmacological Studies on Diphenylalkylamine Derivatives. (II): On the Actions ofl-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 2016-03-04. Retrieved2012-06-30.
  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 2016-03-02. Retrieved2016-02-27.
  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 2017-12-02. Retrieved2016-11-17.
  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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