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Amfepramone

Stimulant drug used as an appetite suppressant


Stimulant drug used as an appetite suppressant

FieldValue
Verifiedfieldschanged
verifiedrevid456687601
imageAmfepramone.svg
image_classskin-invert-image
width220
chiralityRacemic mixture
tradenameTenuate, Tepanil, Nobesine, others
Drugs.com
MedlinePlusa682037
DailyMedIDDiethylpropion
pregnancy_AUB2
routes_of_administrationBy mouth
ATC_prefixA08
ATC_suffixAA03
legal_AUS4
legal_BRB2
legal_BR_comment
legal_CASchedule G (CDSA IV)
legal_CA_comment
legal_DEPrescription only (Anlage III for higher doses)
legal_NZ
legal_UKClass C
legal_USSchedule IV
legal_US_comment
legal_EURx-only
legal_EU_comment
legal_UN
legal_status
elimination_half-life4–6 hours (metabolites)
excretionUrine (75%)
CAS_number_Ref
CAS_number90-84-6
PubChem7029
IUPHAR_ligand7161
DrugBank_Ref
DrugBankDB00937
ChemSpiderID_Ref
ChemSpiderID6762
UNII_Ref
UNIIQ94YYU22B8
KEGG_Ref
KEGGD07444
ChEBI_Ref
ChEBI4530
ChEMBL_Ref
ChEMBL1194666
synonymsDiethylpropion, Diethylcathinone
IUPAC_name(RS)-2-diethylamino-1-phenylpropan-1-one
C13H=19N=1O=1
SMILESO=C(c1ccccc1)C(N(CC)CC)C
StdInChI_Ref
StdInChI1S/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
StdInChIKeyXXEPPPIWZFICOJ-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.

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

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (25 April 2012). "Tenuate Product information".
  3. (25 April 2012). "Nobesine Product information".
  4. "Amfepramone. List of nationally authorized medicinal products".
  5. (12 February 2021). "Amfepramone-containing medicinal products".
  6. (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.
  7. (July 1999). "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances". [[Therapeutic Goods Administration]], Department of Health and Ageing, Australian Government.
  8. (30 January 2013). "Diethylpropion Hydrochloride". Pharmaceutical Press.
  9. (2009). "New Concepts of Psychostimulant Induced Neurotoxicity".
  10. (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry.
  11. "Anorexigenic Propiophenones".
  12. (1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society.
  13. "Class C Drugs". UK Legislation.
  14. (10 June 2022). "EMA recommends withdrawal of marketing authorisation for amfepramone medicines".
  15. (1977). "Diethylpropion (tenuate): an infrequently abused anorectic". Psychosomatics.
  16. (June 2009). "Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse". Journal of Psychopharmacology.
  17. "Tepanil (diethylpropion hydrochloride) tablet, extended release". National Institutes of Health.
  18. (May 1963). "Habituation to diethylpropion (Tenuate)". Canadian Medical Association Journal.
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