Lefetamine

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Lefetamine
Lefetamine.svg
Lefetamine3d.png
Systematic (IUPAC) name
(1R)-N,N-dimethyl-1,2-diphenylethanamine
Clinical data
Legal status Prescription Only (S4) (AU) Schedule IV (US)
Routes Oral
Identifiers
CAS number 7262-75-1 N
ATC code None
PubChem CID 443970
ChemSpider 392017 YesY
UNII 4J9726V5Y9 YesY
Chemical data
Formula C16H19N 
Mol. mass 225.329 g/mol
 N (what is this?)  (verify)

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

Lefetamine was invented in the 1940s and showed weak analgetic activity.[1]

It was investigated in Japan in 1950s.[2] The l-isomere showed weak analgetic 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]

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 for the detoxification of methadone patients and found to be inferior to both for this purpose.[7]

Research[edit]

Some related pyrrylphenylethanones had analgetic activity comparable to morphine.[8] Some pyrrole analogues were reported to have analgetic effects comparable to lefetamine and being devoid of neurotoxic properties.[9]

See also[edit]

References[edit]

  1. ^ Dodds, E. C.; Lawson, W.; Simpson, S. A.; Williams, P. C. (1945). "Testing Diphenylethylamine Compounds for Analgesic Action" (pdf). The Journal of Physiology 104 (1): 47–51. PMC 1393527. PMID 16991666.  edit
  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. 
  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. 
  5. ^ Mannelli, P.; Janiri, L.; de Marinis, M.; Tempesta, E. (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.  edit
  6. ^ Janiri, L.; Mannelli, P.; Pirrongelli, C.; lo Monaco, M.; Tempesta, E. (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.  edit
  7. ^ Janiri, L.; Mannelli, P.; Persico, A. M.; Serretti, A.; Tempesta, E. (1994). "Opiate Detoxification of Methadone Maintenance Patients Using Lefetamine, Clonidine and Buprenorphine". Drug and Alcohol Dependence 36 (2): 139–145. doi:10.1016/0376-8716(94)90096-5. PMID 7851281.  edit
  8. ^ Massa, S.; di Santo, R.; Mai, A.; Artico, M.; Pantaleoni, G. C.; Giorgi, R.; Coppolino, M. F. (1992). "Pyrrylphenylethanones Related to Cathinone and Lefetamine: Synthesis and Pharmacological Activities". Archiv der Pharmazie 325 (7): 403–409. doi:10.1002/ardp.19923250707. PMID 1417455.  edit
  9. ^ Massa, S.; Stefancich, G.; Artico, M.; Corelli, F.; Silvestri, R.; Pantaleoni, G. C.; Fanini, D.; Palumbo, G.; Giorgi, R. (1989). "Synthesis, Neuropsychopharmacological Effects and Analgesic-Antiinflammatory Activities of Pyrrole Analogues of Lefetamine". Farmaco (Societa Chimica Italiana) 44 (9): 763–777. PMID 2604832.  edit