Lefetamine

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

Lefetamine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: Schedule III
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class B
  • US: Schedule IV
Identifiers
IUPAC name
  • (1R)-N,N-dimethyl-1,2-diphenylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H19N
Molar mass225.335 g·mol−1
3D model (JSmol)
SMILES
  • CN([C@@H](C1=CC=CC=C1)CC2=CC=CC=C2)C
InChI
  • 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 Y
  • Key:YEJZJVJJPVZXGX-MRXNPFEDSA-N Y
 NY (what is this?)  (verify)

Discovery

Lefetamine-related 1,2-diphenylethylamines were invented in the 1940s and showed weak analgesic activity.[1]

It was investigated in Japan in 1950s.[2] 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.[3][4]

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.[5]

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.[6]

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.[7]

Regulation may vary; it does not appear as either a narcotic or non-narcotic under the US Controlled Substances Act 1970 [8]

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.[9]

Research

Some related pyrrylphenylethanones had analgetic activity comparable to morphine.[10] Some pyrrole analogues were reported to have analgesic effects comparable to lefetamine and being devoid of neurotoxic properties.[11]

See also

References
  1. 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.
  2. 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 1963-12-27, assigned to Institut Seikatsu Kagaku Kenkyusho (Scientific Research Institute for Practical Life, Kyoto)
  3. 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. Retrieved 2011-09-25.
  4. 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 2016-03-04. Retrieved 2012-06-30.
  5. 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.
  6. 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.
  7. 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. PMID 7851281.
  8. "DEA Diversion Control Division". Archived from the original on 2016-03-02. Retrieved 2016-02-27.
  9. "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. Retrieved 2016-11-17.
  10. 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.
  11. 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. Societa Chimica Italiana. 44 (9): 763–77. PMID 2604832.
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