Amfepramone Explained

Verifiedfields:changed
Verifiedrevid:456687601
Width:220
Chirality:Racemic mixture
Tradename:Tenuate, Tepanil, Nobesine, others
Dailymedid:Diethylpropion
Pregnancy Au:B2
Routes Of Administration:By mouth
Atc Prefix:A08
Atc Suffix:AA03
Legal Au:S4
Legal Br:B2
Legal Br Comment:[1]
Legal Ca:Schedule G (CDSA IV)
Legal Ca Comment:[2] [3]
Legal De:Prescription only (Anlage III for higher doses)
Legal Uk:Class C
Legal Us:Schedule IV
Legal Eu:Rx-only
Legal Eu Comment:[4] [5]
Elimination Half-Life:4 - 6 hours (metabolites)[6]
Excretion:Urine (>75%)
Cas Number:90-84-6
Pubchem:7029
Iuphar Ligand:7161
Drugbank:DB00937
Chemspiderid:6762
Unii:Q94YYU22B8
Kegg:D07444
Chebi:4530
Chembl:1194666
Synonyms:Diethylpropion, Diethylcathinone
Iupac Name:(RS)-2-diethylamino-1-phenylpropan-1-one
C:13
H:19
N:1
O:1
Smiles:O=C(c1ccccc1)C(N(CC)CC)C
Stdinchi:1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
Stdinchikey:XXEPPPIWZFICOJ-UHFFFAOYSA-N

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

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 10× and 20× stronger on norepinephrine in comparison, respectively.[10]

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.

Legal status

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]

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] [17] [18]

Notes and References

  1. Web site: Anvisa . Brazilian Health Regulatory Agency . 2023-03-31 . RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial . Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control. live . https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 . 2023-08-03 . 2023-08-16 . . pt-BR . 2023-04-04.
  2. Web site: Tenuate Product information . . 25 April 2012 . 3 August 2022 . 4 August 2022 . https://web.archive.org/web/20220804002602/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=16693 . live .
  3. Web site: Nobesine Product information . . 25 April 2012 . 3 August 2022 . 4 August 2022 . https://web.archive.org/web/20220804002603/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=9263 . live .
  4. Web site: Amfepramone. List of nationally authorized medicinal products . https://web.archive.org/web/20210827213256/https://www.ema.europa.eu/en/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf . 27 August 2021 . live .
  5. Web site: Amfepramone-containing medicinal products . European Medicines Agency (EMA) . 12 February 2021 . 12 February 2021 . 7 March 2021 . https://web.archive.org/web/20210307060434/https://www.ema.europa.eu/en/medicines/human/referrals/amfepramone-containing-medicinal-products . live .
  6. Web site: SPC-DOC_PL 16133-0001 . Medicines Healthcare products Regulatory Agency . Essential Nutrition Ltd . 18 November 2011 . 18 July 2014 .
  7. Web site: TGA Approved Terminology for Medicines, Section 1 – Chemical Substances . Therapeutic Goods Administration (Tga) . July 1999 . Therapeutic Goods Administration, Department of Health and Ageing, Australian Government . 42 . 18 July 2014 . 11 February 2014 . https://web.archive.org/web/20140211201639/http://www.tga.gov.au/pdf/medicines-approved-terminology-chemical.pdf . live .
  8. Web site: Diethylpropion Hydrochloride . Martindale: The Complete Drug Reference . Pharmaceutical Press . 30 January 2013 . 18 July 2014 . Brayfield A . London, UK . 27 August 2021 . https://web.archive.org/web/20210827213309/https://about.medicinescomplete.com/wp-content/plugins/revslider/public/assets/js/extensions/revolution.extension.layeranimation.min.js?version=5.4.5 . live .
  9. Book: Arias HR, Santamaría A, Ali SF . New Concepts of Psychostimulant Induced Neurotoxicity . Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion . 88 . 223–55 . 2009 . 19897080 . 10.1016/S0074-7742(09)88009-4 . 9780123745040 . International Review of Neurobiology .
  10. Rothman RB, Baumann MH . Therapeutic potential of monoamine transporter substrates . Current Topics in Medicinal Chemistry . 6 . 17 . 1845–59 . 2006 . 17017961 . 10.2174/156802606778249766 . 7 September 2020 . 23 October 2020 . https://web.archive.org/web/20201023101936/https://zenodo.org/record/1235860 . live .
  11. US . patent . 3001910 . Anorexigenic Propiophenones . Schutte J . Temmler-Werke . 1961-09-26 .
  12. Hyde JF, Browning E, Adams R . Journal of the American Chemical Society . 50 . 8 . 2287–2292. Synthetic Homologs of d,l-Ephedrine. 1928 . 10.1021/ja01395a032 .
  13. Web site: Class C Drugs . Schedule 2 Controlled Drugs . UK Legislation . 7 February 2012 . 14 November 2012 . https://web.archive.org/web/20121114181829/http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 . live .
  14. Web site: EMA recommends withdrawal of marketing authorisation for amfepramone medicines . European Medicines Agency (EMA) . 10 June 2022 . 10 June 2022 . 10 June 2022 . https://web.archive.org/web/20220610152019/https://www.ema.europa.eu/en/news/ema-recommends-withdrawal-marketing-authorisation-amfepramone-medicines . live .
  15. Cohen S . Diethylpropion (tenuate): an infrequently abused anorectic . Psychosomatics . 18 . 1 . 28–33 . 1977 . 850721 . 10.1016/S0033-3182(77)71101-6 . free .
  16. Jasinski DR, Krishnan S . Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse . Journal of Psychopharmacology . 23 . 4 . 419–27 . June 2009 . 19329547 . 10.1177/0269881109103113 . 6138292 .
  17. Web site: Tepanil (diethylpropion hydrochloride) tablet, extended release . Dailymed . National Institutes of Health . 4 August 2022 . 8 May 2021 . https://web.archive.org/web/20210508102939/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=79b15110-e484-4b84-8947-15653746773c . live .
  18. Caplan J . Habituation to diethylpropion (Tenuate) . Canadian Medical Association Journal . 88 . 943–4 . May 1963 . 18 . 14018413 . 1921278 .

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