Amfepramone

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Amfepramone
Amfepramone.svg
Systematic (IUPAC) name
(RS)-2-diethylamino-1-phenylpropan-1-one
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682037
Pregnancy cat. B
Legal status Schedule IV (US)
Routes Oral
Identifiers
CAS number 134-80-5 YesY
ATC code A08AA03
PubChem CID 7029
DrugBank DB00937
ChemSpider 6762 YesY
UNII 19V2PL39NG YesY
KEGG D07444 N
ChEBI CHEBI:4530 YesY
ChEMBL CHEMBL1194666 N
Synonyms Diethylpropion
Chemical data
Formula C13H19NO 
Mol. mass 205.30 g/mol
 N (what is this?)  (verify)

Amfepramone (INN, other names diethylcathinone and diethylpropion, trade names Anorex, Linea, Nobesine, Prefamone, Regenon, Tepanil, Tenuate), is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes that is used as an appetite suppressant.

Pharmacology[edit]

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[1] 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.[1] As a result, ethcathinone and amfepramone can essentially be considered norepinephrine releasing agents (NRAs).

Abuse[edit]

Amfepramone is believed to have relatively low abuse potential.,[2][3][4][5] but recently there have been reports of teens and adults in the UK abusing this drug, known as "tombstones" to the abusers.

Legality[edit]

Amfepramone is classified as a Schedule IV controlled substance in the United States. In the UK Amfepramone is a class C drug [6] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.

Chemistry[edit]

  1. Propiophenone is brominated to produce α-bromopropiophenone.
  2. This is reacted with diethylamine to yield the product, diethylpropion.[7][8]

See also[edit]

References[edit]

  1. ^ a b Rothman, R. B.; Baumann, M. H. (2006). "Therapeutic Potential of Monoamine Transporter Substrates". Current Topics in Medicinal Chemistry 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961. 
  2. ^ Cohen, S. (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721. 
  3. ^ Jasinski, D. R.; Krishnan, S. (June 2009). "Abuse Liability and Safety of Oral Lisdexamfetamine Dimesylate in Individuals with a History of Stimulant Abuse". Journal of Psychopharmacology 23 (4): 419–427. doi:10.1177/0269881109103113. PMID 19329547. 
  4. ^ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health. 
  5. ^ Caplan, J. (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal 88: 943–944. PMC 1921278. PMID 14018413. 
  6. ^ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation. 
  7. ^ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke 
  8. ^ Hyde, J. F.; Browning, E.; Adams, R. (1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society 50 (8): 2287–2292. doi:10.1021/ja01395a032.  edit