Lefetamine
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| Systematic (IUPAC) name | |
| (1R)-N,N-dimethyl-1,2-diphenylethanamine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule IV (USA) |
| Routes | Oral |
| Identifiers | |
| CAS number | 7262-75-1  |
| ATC code | None |
| PubChem | CID 443970 |
| ChemSpider | 392017 |
| UNII | 4J9726V5Y9 |
| Chemical data | |
| Formula | C16H19N |
| Mol. mass | 225.329 g/mol |
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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]
[edit] Research
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]
[edit] See also
[edit] References
- ^ 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. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1393527/pdf/jphysiol01495-0059.pdf.
- ^ 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)
- ^ 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. http://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/75783/1/chd039_1_067.pdf.
- ^ 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. http://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/75782/1/chd039_1_078.pdf.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Massa, S.; Stefancich, G.; Artico, M.; Corelli, F.; Silvestri, R.; Pantaleoni, G. C.; Fanini, D.; Palumbo, G. et al. (1989). "Synthesis, Neuropsychopharmacological Effects and Analgesic-Antiinflammatory Activities of Pyrrole Analogues of Lefetamine". Farmaco (Societa Chimica Italiana) 44 (9): 763–777. PMID 2604832.
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