Amfepramone

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Amfepramone
File:(RS)-Amfepramone-Structural Formulae V1.svg
Clinical data
Trade namesTenuate
SynonymsDiethylpropion
AHFS/Drugs.comMonograph
MedlinePlusa682037
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life4-6 hours (metabolites)[1]
ExcretionUrine (>75%)[1]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
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Chemical and physical data
FormulaC13H19NO
Molar mass205.30 g/mol
3D model (JSmol)
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Amfepramone (INN)[note 1] is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant.[2][3] It is used in the short-term management of obesity, along with dietary and lifestyle changes.[2] Amfepramone is most closely chemically related to the antidepressant and smoking cessation aid bupropion (previously called amfebutamone), which has also been developed as a weight-loss medicine when in a combination product with naltrexone.[4]

Pharmacology

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[5] Ethcathinone (and therefore amfepramone as well) is a very weak dopaminergic and serotonergic, and is approximately 10x and 20x stronger on norepinephrine in comparison, respectively.[5] As a result, ethcathinone and amfepramone can essentially be considered a member of the class of drugs known as norepinephrine releasing agents (NRAs).

Abuse

Amfepramone is believed to have relatively low abuse potential.[6][7][8][9] but recently there have been reports of teens and adults in the UK abusing this drug, known as "tombstones" to the abusers.

Legality

Amfepramone is classified as a Schedule IV controlled substance in the United States. It is also a Schedule IV controlled substance in Canada. In the UK Amfepramone is a class C drug [10] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody. It's not US FDA approved.

Chemistry

  1. Propiophenone is brominated to produce α-bromopropiophenone.
  2. This is reacted with diethylamine to yield the product, diethylpropion.[11][12]

See also

Notes

  1. ↑ Another medically-utilized name is diethylpropion (BAN and AAN). Chemical names include: α-methyl-β-keto-N,N-diethylphenethylamine, N,N-diethyl-β-ketoamphetamine and N,N-diethylcathinone. Brand names include: Anorex, Linea, Nobesine, Prefamone, Regenon, Tepanil and Tenuate.

References

  1. ↑ 1.0 1.1 "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
  2. ↑ 2.0 2.1 Brayfield, A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.
  3. ↑ Template:Cite document
  4. ↑ Arias, HR; Santamaría, A; Ali, SF (2009). "Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion". International Review of Neurobiology. 88: 223–55. doi:10.1016/S0074-7742(09)88009-4. PMID 19897080.
  5. ↑ 5.0 5.1 Rothman, RB; Baumann, MH (2006). "Therapeutic Potential of Monoamine Transporter Substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
  6. ↑ Cohen, S (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.
  7. ↑ Jasinski, DR; Krishnan, S (June 2009). "Abuse Liability and Safety of Oral Lisdexamfetamine Dimesylate in Individuals with a History of Stimulant Abuse". Journal of Psychopharmacology. 23 (4): 419–427. doi:10.1177/0269881109103113. PMID 19329547.
  8. ↑ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health.
  9. ↑ Caplan, J (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal. 88: 943–944. PMC 1921278. PMID 14018413.
  10. ↑ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation.
  11. ↑ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke 
  12. ↑ Template:Cite doi


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