Amfepramone

Stimulant drug used as an appetite suppressant From Wikipedia, the free encyclopedia

Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant.[8][9] 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.[10]

Trade namesTenuate, Tepanil, Nobesine, others
Other namesDiethylpropion, Diethylcathinone
Quick facts Clinical data, Trade names ...
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
Pharmacokinetic data
Elimination half-life46 hours (metabolites)[7]
ExcretionUrine (>75%)[7]
Identifiers
  • (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 Edit this at Wikidata
Chemical and physical data
FormulaC13H19NO
Molar mass205.301 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C(c1ccccc1)C(N(CC)CC)C
  • 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 checkY
  • Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N checkY
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Pharmacology

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

Chemistry

Amfepramone can be synthesized from propiophenone by bromination, followed by reaction with diethylamine.[12][13]

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[14] 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.[15][6]

Recreational use

The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.[16][17][4][18]

References

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