Lefetamine

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Chemical compound

title: "Lefetamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["mu-opioid-receptor-agonists", "norepinephrine–dopamine-reuptake-inhibitors", "stimulants", "1,2-diarylethylamines", "dimethylamino-compounds", "phenyl-compounds", "substituted-amphetamines", "tertiary-amines"] description: "Chemical compound" topic_path: "general/mu-opioid-receptor-agonists" source: "https://en.wikipedia.org/wiki/Lefetamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

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| tradename = | pregnancy_category = | legal_AU = S4 | legal_BR = B1 | legal_BR_comment = | legal_CA = Schedule III | legal_US = Schedule IV | legal_UK = Class B | legal_DE = Anlage I | routes_of_administration = Oral

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 7262-75-1 | ATC_prefix = none | ATC_suffix = | PubChem = 443970 | ChemSpiderID_Ref = | ChemSpiderID = 392017 | UNII_Ref = | UNII = 4J9726V5Y9

| C=16 | H=19 | N=1 | smiles = CN(C@@HCC2=CC=CC=C2)C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = YEJZJVJJPVZXGX-MRXNPFEDSA-N

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

Discovery

The parent structure of lefetamine, 1,2-diphenylethylamine was first synthesized in the 1940s and showed weak analgesic activity.

Lefetamine itself was first investigated in Japan in the 1950s. 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.

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.

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.

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.

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

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.

Research

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

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (June 1945). "Testing diphenylethylamine compounds for analgesic action". The Journal of Physiology.
  3. "Verfahren zur Herstellung von antitussiv wirksamem ''l''-1,2-Diphenyl-1-dimethylaminoaethan und dessen Salzen".
  4. (1961). "Pharmacological Studies on Diphenylalkylamine Derivatives. (I)". Bulletin of the Institute for Chemical Research, Kyoto University.
  5. (1961). "Pharmacological Studies on Diphenylalkylamine Derivatives. (II): On the Actions of ''l''-1,2-Diphenyl-1-dimethylaminoethane Hydrochloride (SPA)". Bulletin of the Institute for Chemical Research, Kyoto University.
  6. (October 1989). "Lefetamine: new abuse of an old drug--clinical evaluation of opioid activity". Drug and Alcohol Dependence.
  7. (January 1989). "Lephetamine abuse and dependence: clinical effects and withdrawal syndrome". British Journal of Addiction.
  8. (October 1994). "Opiate detoxification of methadone maintenance patients using lefetamine, clonidine and buprenorphine". Drug and Alcohol Dependence.
  9. "DEA Diversion Control Division".
  10. (June 2016). "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)".
  11. (July 1992). "Pyrrylphenylethanones related to cathinone and lefetamine: synthesis and pharmacological activities". Archiv der Pharmazie.
  12. (September 1989). "Synthesis, neuropsychopharmacological effects and analgesic-antiinflammatory activities of pyrrole analogues of lefetamine". Societa Chimica Italiana.

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mu-opioid-receptor-agonistsnorepinephrine–dopamine-reuptake-inhibitorsstimulants1,2-diarylethylaminesdimethylamino-compoundsphenyl-compoundssubstituted-amphetaminestertiary-amines