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Amfepramone

Amfepramone
Amfepramone.svg
Clinical data
Trade namesTenuate
Other namesDiethylpropion
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
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.836 Edit this at Wikidata
Chemical and physical data
FormulaC13H19NO
Molar mass205.30 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
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Amfepramone, also known as diethylpropion, 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]

Abuse

Amfepramone is believed to have relatively low abuse potential.[5][6][7][8] but recently there have been reports of teens and adults in the UK abusing this drug, known as "tombstones" to the abusers.

Pharmacology

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[9] 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.[9] As a result, ethcathinone and amfepramone can essentially be considered a member of the class of drugs known as norepinephrine releasing agents (NRAs).

Chemistry

Amfepramone can be synthesized from propiophenone by bromination, followed by reaction with diethylamine.[10][11]

Society and culture

Names

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.

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 [12] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.

See also

References

  1. ^ a b "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.[permanent dead link]
  2. ^ a b Brayfield, A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.
  3. ^ "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999: 42. Cite journal requires |journal= (help)
  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. ISBN 9780123745040. PMID 19897080. Cite journal requires |journal= (help)
  5. ^ Cohen, S (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.[permanent dead link]
  6. ^ 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.
  7. ^ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health.
  8. ^ Caplan, J (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal. 88: 943–944. PMC 1921278. PMID 14018413.
  9. ^ a b 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. Archived from the original on 2017-03-26. Retrieved 2019-04-17.
  10. ^ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke 
  11. ^ Hyde, J. F.; Browning, E.; Adams, R. (1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society. 50 (8): 2287–2292. doi:10.1021/ja01395a032.
  12. ^ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation.