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| Clinical data | |
|---|---|
| Trade names | Tenuate, Tepanil, Nobesine, others |
| Other names | Diethylpropion, Diethylcathinone |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682037 |
| License data | |
| Pregnancy category |
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| Routes of administration |
By mouth |
| ATC code | |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Elimination half-life | 4-6 hours (metabolites) |
| Excretion | Urine (>75%) |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.001.836 |
| Chemical and physical data | |
| Formula | C13H19NO |
| Molar mass | 205.301 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic 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. 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 10x and 20x stronger on norepinephrine in comparison, respectively. 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.
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.
External links
- "Amfepramone". Drug Information Portal. U.S. National Library of Medicine.