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Amfepramone

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Amfepramone
Amfepramone.svg
Clinical data
Trade names Tenuate, Tepanil, Nobesine, others
Other names Diethylpropion, Diethylcathinone
AHFS/Drugs.com Monograph
MedlinePlus a682037
License data
Pregnancy
category
  • AU: B2
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 4-6 hours (metabolites)
Excretion Urine (>75%)
Identifiers
  • (RS)-2-diethylamino-1-phenylpropan-1-one
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
  • 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
 ☒NcheckY (what is this?)  (verify)

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.

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