Lefetamine

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Lefetamine
Lefetamine.svg
Lefetamine3d.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • (1R)-N,N-dimethyl-1,2-diphenylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H19N
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 Yes check.svgY
  • Key:YEJZJVJJPVZXGX-MRXNPFEDSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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

Contents

Discovery

Lefetamine-related 1,2-diphenylethylamines were invented in the 1940s and showed weak analgesic activity. [2]

It was investigated in Japan in the 1950s. [3] 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. [4] [5]

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. [6]

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. [7]

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. [8]

Regulation may vary; it does not appear as either a narcotic or non-narcotic under the US Controlled Substances Act 1970 [9]

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. [10]

Research

Some related pyrrylphenylethanones had analgesic activity comparable to morphine. [11] Some pyrrole analogues were reported to have analgesic effects comparable to lefetamine and being devoid of neurotoxic properties. [12]

See also

Related Research Articles

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<span class="mw-page-title-main">Opioid use disorder</span> Medical condition

Opioid use disorder (OUD) is a substance use disorder characterized by cravings for opioids, continued use despite physical and/or psychological deterioration, increased tolerance with use, and withdrawal symptoms after discontinuing opioids. Opioid withdrawal symptoms include nausea, muscle aches, diarrhea, trouble sleeping, agitation, and a low mood. Addiction and dependence are important components of opioid use disorder.

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Buprenorphine, sold under the brand name Subutex among others, is an opioid used to treat opioid use disorder, acute pain, and chronic pain. It can be used under the tongue (sublingual), in the cheek (buccal), by injection, as a skin patch (transdermal), or as an implant. For opioid use disorder, the patient must have moderate opioid withdrawal symptoms before buprenorphine can be administered under direct observation of a health-care provider.

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<span class="mw-page-title-main">Ethylmorphine</span> Opioid analgesic and antitussive drug

Ethylmorphine is an opioid analgesic and antitussive.

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<span class="mw-page-title-main">Nalbuphine</span> Opioid analgesic

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<span class="mw-page-title-main">Codeine</span> Opiate and prodrug of morphine used to treat pain

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<span class="mw-page-title-main">Benzylmorphine</span> Opioid analgesic and cough suppressant drug

Benzylmorphine (Peronine) is a semi-synthetic opioid narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the morphine molecule just as the methyl group creates codeine and the ethyl group creates ethylmorphine or dionine. It is about 90% as strong as codeine by weight.

<span class="mw-page-title-main">Oripavine</span> Chemical compound

Oripavine is an opioid and the major metabolite of thebaine. It is the parent compound from which a series of semi-synthetic opioids are derived, which includes the compounds etorphine and buprenorphine. Although its analgesic potency is comparable to morphine, it is not used clinically due to its severe toxicity and low therapeutic index. Due to its use in manufacture of strong opioids, oripavine is a controlled substance in some jurisdictions.

<span class="mw-page-title-main">Tapentadol</span> Opioid analgesic of benzenoid class

Tapentadol, brand names Nucynta among others, is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours.

<span class="mw-page-title-main">Propiram</span> Opioid analgesic drug

Propiram is a partial μ-opioid receptor agonist and weak μ antagonist analgesic from the ampromide family of drugs related to other drugs such as phenampromide and diampromide. It was invented in 1963 in the United Kingdom by Bayer but was not widely marketed, although it saw some limited clinical use, especially in dentistry. Propiram reached Phase III clinical trials in the United States and Canada.

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<span class="mw-page-title-main">Opiate</span> Substance derived from opium

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<span class="mw-page-title-main">MT-45</span> Chemical compound

MT-45 (IC-6) is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co. It is chemically a 1-substituted-4-(1,2-diphenylethyl) piperazine derivative, which is structurally unrelated to most other opioid drugs. Racemic MT-45 has around 80% the potency of morphine, with almost all opioid activity residing in the (S) enantiomer. It has been used as a lead compound from which a large family of potent opioid drugs have been developed, including full agonists, partial agonists, and antagonists at the three main opioid receptor subtypes. Fluorinated derivatives of MT-45 such as 2F-MT-45 are significantly more potent as μ-opioid receptor agonists, and one of its main metabolites 1,2-diphenylethylpiperazine also blocks NMDA receptors.

<span class="mw-page-title-main">AD-1211</span> Opioid analgesic drug

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<span class="mw-page-title-main">Amorphinism</span> Medical condition

Amorphinism refers to the mental and physical symptoms arising when a morphine-addict is deprived of morphine. Morphine is a potent opioid agonist derived from poppy plants and was originally used as a painkiller before being abused for euphoric and relieving purposes. It gave rise to morphine dependence, which caused the development of morphine withdrawal symptoms when morphine is reduced or stopped.

References

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  2. 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.
  3. DEpatent 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)
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  5. 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.
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  8. 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.
  9. "DEA Diversion Control Division". Archived from the original on 2016-03-02. Retrieved 2016-02-27.
  10. "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.
  11. 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.
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