関: lefetamine hydrochloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/15 21:23:54」(JST)

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

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]

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

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

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.
^ 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.
^ 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.
^ 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.; 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.

English Journal

Pharmacological Investigations of the Dissociative 'Legal Highs' Diphenidine, Methoxphenidine and Analogues.

Wallach J1, Kang H2, Colestock T1, Morris H1, Bortolotto ZA3, Collingridge GL3,4,5, Lodge D3, Halberstadt AL6, Brandt SD7, Adejare A1.
PloS one.PLoS One.2016 Jun 17;11(6):e0157021. doi: 10.1371/journal.pone.0157021. eCollection 2016.
1,2-Diarylethylamines including lanicemine, lefetamine, and remacemide have clinical relevance in a range of therapeutic areas including pain management, epilepsy, neurodegenerative disease and depression. More recently 1,2-diarylethylamines have been sold as 'legal highs' in a number of different f
PMID 27314670

Toxicokinetics of lefetamine and derived diphenylethylamine designer drugs-Contribution of human cytochrome P450 isozymes to their main phase I metabolic steps.

Wink CS1, Meyer GM1, Meyer MR1, Maurer HH2.
Toxicology letters.Toxicol Lett.2015 Nov 4;238(3):39-44. doi: 10.1016/j.toxlet.2015.08.012. Epub 2015 Aug 11.
Lefetamine was first marketed in the 1940s as an opioid analgesic. Since withdrawal symptoms were observed during treatment, it became a controlled substance. Its N-ethyl and N-iso-propyl derivatives appeared on the illicit drug market in 2008. Metabolism studies for lefetamine and these derivatives
PMID 26276083

Lefetamine, a controlled drug and pharmaceutical lead of new designer drugs: synthesis, metabolism, and detectability in urine and human liver preparations using GC-MS, LC-MS(n), and LC-high resolution-MS/MS.

Wink CS1, Meyer GM, Zapp J, Maurer HH.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2015 Feb;407(6):1545-57. doi: 10.1007/s00216-014-8414-3. Epub 2015 Jan 11.
Lefetamine (N,N-dimethyl-1,2-diphenylethylamine, L-SPA) was marketed as an opioid analgesic in Japan and Italy. After being widely abused, it became a controlled substance. It seems to be a pharmaceutical lead for designer drugs because N-ethyl-1,2-diphenylethylamine (NEDPA) and N-iso-propyl-1,2-dip
PMID 25577353

★リンクテーブル★

リンク元	「レフェタミン」
拡張検索	「lefetamine hydrochloride」

「レフェタミン」

Lefetamine
Systematic (IUPAC) name
	(1R)-N,N-dimethyl-1,2-diphenylethanamine
Clinical data
Legal status	AU: S4 (Prescription only); DE: Anlage I; UK: Class B; US: Schedule IV;
Routes of; administration	Oral
Identifiers
CAS Number	7262-75-1
ATC code	None
PubChem	CID: 443970
ChemSpider	392017
UNII	4J9726V5Y9
Chemical data
Formula	C16H19N
Molecular mass	225.329 g/mol
	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 ; Key:YEJZJVJJPVZXGX-MRXNPFEDSA-N ;
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