Lefetamine Routes of administration Oral ATC code Legal status
AU : S4 (Prescription only)
CA : Schedule III
DE : Anlage I (Authorized scientific use only)
UK : Class B
US : Schedule IV
(1R )-N ,N -dimethyl-1,2-diphenylethanamine
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 16 H 19 N Molar mass 225.335 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
Y Key:YEJZJVJJPVZXGX-MRXNPFEDSA-N
Y
N Y (what is this?)
Lefetamine (Santenol ) is a drug which is a stimulant and also an analgesic with effects comparable to codeine .
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 [ ]
^ 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 .
^ 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. Archived (PDF) from the original on 2012-05-01. Retrieved 2011-09-25 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ "DEA Diversion Control Division" . Archived from the original on 2016-03-02. Retrieved 2016-02-27 .
^ "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 .
^ 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 .
^ 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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See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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