amfepramone
{{Short description|Stimulant drug used as an appetite suppressant}}
{{redirect|Keramik}}
{{Use dmy dates|date=August 2022}}
{{Infobox drug
| Verifiedfields = changed
| verifiedrevid = 456687601
| image = Amfepramone.svg
| image_class = skin-invert-image
| width = 220
| alt =
| chirality = Racemic mixture
| pronounce =
| tradename = Tenuate, Tepanil, Nobesine, others
| Drugs.com = {{drugs.com|monograph|diethylpropion-hydrochloride}}
| MedlinePlus = a682037
| DailyMedID = Diethylpropion
| pregnancy_AU = B2
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = By mouth
| class =
| ATC_prefix = A08
| ATC_suffix = AA03
| ATC_supplemental =
| legal_AU = S4
| legal_AU_comment =
| legal_BR = B2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=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 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
| legal_CA = Schedule G (CDSA IV)
| legal_CA_comment = {{cite web | title=Tenuate Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=16693 | access-date=3 August 2022 | archive-date=4 August 2022 | archive-url=https://web.archive.org/web/20220804002602/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=16693 | url-status=live }}{{cite web | title=Nobesine Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=9263 | access-date=3 August 2022 | archive-date=4 August 2022 | archive-url=https://web.archive.org/web/20220804002603/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=9263 | url-status=live }}
| legal_DE = Prescription only (Anlage III for higher doses)
| legal_DE_comment =
| legal_NZ =
| legal_NZ_comment =
| legal_UK = Class C
| legal_UK_comment =
| legal_US = Schedule IV
| legal_EU = Rx-only
| legal_EU_comment = {{cite web | url=https://www.ema.europa.eu/en/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf | title=Amfepramone. List of nationally authorized medicinal products | archive-url=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 | archive-date=27 August 2021 |url-status=live }}{{cite web | title=Amfepramone-containing medicinal products | website=European Medicines Agency (EMA) | date=12 February 2021 | url=https://www.ema.europa.eu/en/medicines/human/referrals/amfepramone-containing-medicinal-products | access-date=12 February 2021 | archive-date=7 March 2021 | archive-url=https://web.archive.org/web/20210307060434/https://www.ema.europa.eu/en/medicines/human/referrals/amfepramone-containing-medicinal-products | url-status=live }}
| legal_UN =
| legal_UN_comment =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life = 4–6 hours (metabolites){{cite web|title=SPC-DOC_PL 16133-0001 |work=Medicines Healthcare products Regulatory Agency |publisher=Essential Nutrition Ltd |date=18 November 2011 |access-date=18 July 2014 |url=http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1396847771265.pdf }}{{dead link|date=July 2017 |bot=InternetArchiveBot |fix-attempted=yes }}
| duration_of_action =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 90-84-6
| CAS_supplemental =
| PubChem = 7029
| IUPHAR_ligand = 7161
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00937
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6762
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q94YYU22B8
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D07444
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4530
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1194666
| NIAID_ChemDB =
| PDB_ligand =
| 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_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XXEPPPIWZFICOJ-UHFFFAOYSA-N
| density =
| density_notes =
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| specific_rotation =
}}
Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant.{{cite web | title=TGA Approved Terminology for Medicines, Section 1 – Chemical Substances | newspaper=Therapeutic Goods Administration (Tga) | date=July 1999 | publisher=Therapeutic Goods Administration, Department of Health and Ageing, Australian Government | page=42 | url=http://www.tga.gov.au/pdf/medicines-approved-terminology-chemical.pdf | access-date=18 July 2014 | archive-date=11 February 2014 | archive-url=https://web.archive.org/web/20140211201639/http://www.tga.gov.au/pdf/medicines-approved-terminology-chemical.pdf | url-status=live }} It is used in the short-term management of obesity, along with dietary and lifestyle changes.{{cite web |title=Diethylpropion Hydrochloride |work=Martindale: The Complete Drug Reference |publisher=Pharmaceutical Press |date=30 January 2013 |access-date=18 July 2014 |url=https://www.medicinescomplete.com/mc/martindale/current/1475-e.htm |veditors=Brayfield A |location=London, UK |archive-date=27 August 2021 |archive-url=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 |url-status=live }} 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.{{cite book | vauthors = Arias HR, Santamaría A, Ali SF | title = New Concepts of Psychostimulant Induced Neurotoxicity | chapter = Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion | volume = 88 | pages = 223–55 | date = 2009 | pmid = 19897080 | doi = 10.1016/S0074-7742(09)88009-4 | isbn = 9780123745040 | series = International Review of Neurobiology }}
Pharmacology
Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Current Topics in Medicinal Chemistry | volume = 6 | issue = 17 | pages = 1845–59 | year = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = https://zenodo.org/record/1235860 | access-date = 7 September 2020 | archive-date = 23 October 2020 | archive-url = https://web.archive.org/web/20201023101936/https://zenodo.org/record/1235860 | url-status = live }} 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.
Chemistry
Amfepramone can be synthesized from propiophenone by bromination, followed by reaction with diethylamine.{{ cite patent | country = US | status = patent | number = 3001910 | title = Anorexigenic Propiophenones | inventor = Schutte J | assign1 = Temmler-Werke | gdate = 1961-09-26 }}{{cite journal | vauthors = Hyde JF, Browning E, Adams R | journal = Journal of the American Chemical Society | volume = 50 | issue = 8 | pages = 2287–2292| title = Synthetic Homologs of d,l-Ephedrine| year = 1928 | doi = 10.1021/ja01395a032 | bibcode = 1928JAChS..50.2287H }}
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 {{cite web | url = http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 | work = Schedule 2 Controlled Drugs | title = Class C Drugs | publisher = UK Legislation | access-date = 7 February 2012 | archive-date = 14 November 2012 | archive-url = https://web.archive.org/web/20121114181829/http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 | url-status = live }} 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.{{cite web | title=EMA recommends withdrawal of marketing authorisation for amfepramone medicines | website=European Medicines Agency (EMA) | date=10 June 2022 | url=https://www.ema.europa.eu/en/news/ema-recommends-withdrawal-marketing-authorisation-amfepramone-medicines | access-date=10 June 2022 | archive-date=10 June 2022 | archive-url=https://web.archive.org/web/20220610152019/https://www.ema.europa.eu/en/news/ema-recommends-withdrawal-marketing-authorisation-amfepramone-medicines | url-status=live }}
= Recreational use =
The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.{{cite journal | vauthors = Cohen S | title = Diethylpropion (tenuate): an infrequently abused anorectic | journal = Psychosomatics | volume = 18 | issue = 1 | pages = 28–33 | year = 1977 | pmid = 850721 | doi = 10.1016/S0033-3182(77)71101-6 | doi-access = free }}{{cite journal | vauthors = Jasinski DR, Krishnan S | title = Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse | journal = Journal of Psychopharmacology | volume = 23 | issue = 4 | pages = 419–27 | date = June 2009 | pmid = 19329547 | doi = 10.1177/0269881109103113 | s2cid = 6138292 }}{{cite web | url = https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=79b15110-e484-4b84-8947-15653746773c | title = Tepanil (diethylpropion hydrochloride) tablet, extended release | work = Dailymed | publisher = National Institutes of Health | access-date = 4 August 2022 | archive-date = 8 May 2021 | archive-url = https://web.archive.org/web/20210508102939/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=79b15110-e484-4b84-8947-15653746773c | url-status = live }}{{cite journal | vauthors = Caplan J | title = Habituation to diethylpropion (Tenuate) | journal = Canadian Medical Association Journal | volume = 88 | pages = 943–4 | date = May 1963 | issue = 18 | pmid = 14018413 | pmc = 1921278 }}
References
{{Reflist}}
{{Anorectics}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
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Category:Diethylamino compounds