Amfepramone

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Amfepramone
Amfepramone.svg
Systematic (IUPAC) name
(RS)-2-diethylamino-1-phenylpropan-1-one
Clinical data
Trade names Tenuate
AHFS/Drugs.com monograph
MedlinePlus a682037
Pregnancy cat. B (US)
Legal status Prescription Only (S4) (AU) POM (UK) Schedule IV (US)
Routes Oral
Pharmacokinetic data
Half-life 4-6 hours (metabolites)[1]
Excretion Urine (>75%)[1]
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), or diethylpropion (BAN and AAN) also known by the chemical name diethylcathinone and the 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.[2][3]

Pharmacology[edit]

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[4] 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.[4] 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.[5][6][7][8] 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 [9] 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.[10][11]

See also[edit]

References[edit]

  1. ^ a b "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014. 
  2. ^ Brayfield, A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014. 
  3. ^ TGA Approved Terminology for Medicines, Section 1 – Chemical Substances (PDF). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999. p. 42. 
  4. ^ a b Rothman, RB; Baumann, MH (2006). "Therapeutic Potential of Monoamine Transporter Substrates". Current Topics in Medicinal Chemistry 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961. 
  5. ^ Cohen, S (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721. 
  6. ^ Jasinski, DR; 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. 
  7. ^ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health. 
  8. ^ Caplan, J (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal 88: 943–944. PMC 1921278. PMID 14018413. 
  9. ^ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation. 
  10. ^ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke 
  11. ^ 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