Amfepramone

Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant.[7][8] It is used in the short-term management of obesity, along with dietary and lifestyle changes.[7] 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.[9]

Amfepramone
Clinical data
Trade namesTenuate, Tepanil, Nobesine, others
Other namesDiethylpropion, Diethylcathinone
AHFS/Drugs.comMonograph
MedlinePlusa682037
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: Schedule G (CDSA IV) [1][2]
  • DE: Prescription only (Anlage III for higher doses)
  • UK: Class C
  • US: Schedule IV [3]
  • EU: Rx-only [4][5]
Pharmacokinetic data
Elimination half-life4-6 hours (metabolites)[6]
ExcretionUrine (>75%)[6]
Identifiers
IUPAC name
  • (RS)-2-diethylamino-1-phenylpropan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.836
Chemical and physical data
FormulaC13H19NO
Molar mass205.301 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C(c1ccccc1)C(N(CC)CC)C
InChI
  • InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3 Y
  • Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pharmacology

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[10] 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.[10] 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.[11][12]

Society and culture

Names

Another medically-utilized name is diethylpropion (British Approved Name (BAN) and Australian Approved Name (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.

Amfepramone is classified as a Schedule IV controlled substance in the United States. In the UK amfepramone is a class C drug [13] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.

As of June 2022, the safety committee of the European Medicines Agency (EMA) recommends the withdrawal of marketing authorizations for amfepramone.[14][5]

Recreational use

The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.[15][16][3][17]

References
  1. "Tenuate Product information". Health Canada. 25 April 2012. Archived from the original on 4 August 2022. Retrieved 3 August 2022.
  2. "Nobesine Product information". Health Canada. 25 April 2012. Archived from the original on 4 August 2022. Retrieved 3 August 2022.
  3. "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health. Archived from the original on 8 May 2021. Retrieved 4 August 2022.
  4. https://www.ema.europa.eu/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf Archived 27 August 2021 at the Wayback Machine
  5. "Amfepramone-containing medicinal products". European Medicines Agency (EMA). 12 February 2021. Archived from the original on 7 March 2021. Retrieved 12 February 2021.
  6. "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
  7. Brayfield A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Archived from the original on 27 August 2021. Retrieved 18 July 2014.
  8. "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF). Therapeutic Goods Administration (Tga). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999. p. 42. Archived (PDF) from the original on 11 February 2014. Retrieved 18 July 2014.
  9. Arias HR, Santamaría A, Ali SF (2009). "Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion". New Concepts of Psychostimulant Induced Neurotoxicity. International Review of Neurobiology. Vol. 88. pp. 223–55. doi:10.1016/S0074-7742(09)88009-4. ISBN 9780123745040. PMID 19897080.
  10. Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–59. doi:10.2174/156802606778249766. PMID 17017961. Archived from the original on 23 October 2020. Retrieved 7 September 2020.
  11. US patent 3001910, Schutte J, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke
  12. Hyde JF, 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.
  13. "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation. Archived from the original on 14 November 2012. Retrieved 7 February 2012.
  14. "EMA recommends withdrawal of marketing authorisation for amfepramone medicines". European Medicines Agency (EMA). 10 June 2022. Archived from the original on 10 June 2022. Retrieved 10 June 2022.
  15. Cohen S (1977). "Diethylpropion (tenuate): an infrequently abused anorectic". Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.
  16. 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): 419–27. doi:10.1177/0269881109103113. PMID 19329547. S2CID 6138292.
  17. Caplan J (May 1963). "Habituation to diethylpropion (Tenuate)". Canadian Medical Association Journal. 88: 943–4. PMC 1921278. PMID 14018413.
  • "Amfepramone". Drug Information Portal. U.S. National Library of Medicine.
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