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Amfepramone
Stimulant drug used as an appetite suppressant
Stimulant drug used as an appetite suppressant
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | changed | |||
| verifiedrevid | 456687601 | |||
| image | Amfepramone.svg | |||
| image_class | skin-invert-image | |||
| width | 220 | |||
| chirality | Racemic mixture | |||
| tradename | Tenuate, Tepanil, Nobesine, others | |||
| Drugs.com | ||||
| MedlinePlus | a682037 | |||
| 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 | ||||
| legal_CA | Schedule G (CDSA IV) | |||
| legal_CA_comment | ||||
| legal_DE | Prescription only (Anlage III for higher doses) | |||
| legal_NZ | ||||
| legal_UK | Class C | |||
| legal_US | Schedule IV | |||
| legal_US_comment | ||||
| legal_EU | Rx-only | |||
| legal_EU_comment | ||||
| legal_UN | ||||
| legal_status | ||||
| elimination_half-life | 4–6 hours (metabolites) | |||
| excretion | Urine (75%) | |||
| CAS_number_Ref | ||||
| CAS_number | 90-84-6 | |||
| PubChem | 7029 | |||
| IUPHAR_ligand | 7161 | |||
| DrugBank_Ref | ||||
| DrugBank | DB00937 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 6762 | |||
| UNII_Ref | ||||
| UNII | Q94YYU22B8 | |||
| KEGG_Ref | ||||
| KEGG | D07444 | |||
| ChEBI_Ref | ||||
| ChEBI | 4530 | |||
| ChEMBL_Ref | ||||
| 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_Ref | ||||
| 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_Ref | ||||
| StdInChIKey | XXEPPPIWZFICOJ-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life = 4–6 hours (metabolites)
Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant. It is used in the short-term management of obesity, along with dietary and lifestyle changes. 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.
Pharmacology
Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone. 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.
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 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.
Recreational use
The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.
References
References
- Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
- (25 April 2012). "Tenuate Product information".
- (25 April 2012). "Nobesine Product information".
- "Amfepramone. List of nationally authorized medicinal products".
- (12 February 2021). "Amfepramone-containing medicinal products".
- (18 November 2011). ["SPC-DOC_PL 16133-0001"](http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1396847771265.pdf }}{{dead link). Essential Nutrition Ltd.
- (July 1999). "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances". [[Therapeutic Goods Administration]], Department of Health and Ageing, Australian Government.
- (30 January 2013). "Diethylpropion Hydrochloride". Pharmaceutical Press.
- (2009). "New Concepts of Psychostimulant Induced Neurotoxicity".
- (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry.
- "Anorexigenic Propiophenones".
- (1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society.
- "Class C Drugs". UK Legislation.
- (10 June 2022). "EMA recommends withdrawal of marketing authorisation for amfepramone medicines".
- (1977). "Diethylpropion (tenuate): an infrequently abused anorectic". Psychosomatics.
- (June 2009). "Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse". Journal of Psychopharmacology.
- "Tepanil (diethylpropion hydrochloride) tablet, extended release". National Institutes of Health.
- (May 1963). "Habituation to diethylpropion (Tenuate)". Canadian Medical Association Journal.
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