Amfepramone

Amfepramone
Systematic (IUPAC) name
(RS)-2-diethylamino-1-phenylpropan-1-one
Clinical data
Trade names Tenuate
AHFS/Drugs.com monograph
MedlinePlus a682037
Pregnancy
category
  • US: B (No risk in non-human studies)
Legal status
Routes of
administration		 Oral
Pharmacokinetic data
Biological half-life 4-6 hours (metabolites)[1]
Excretion Urine (>75%)[1]
Identifiers
CAS Number 134-80-5 YesY
ATC code A08AA03
PubChem CID 7029
IUPHAR/BPS 7161
DrugBank DB00937 YesY
ChemSpider 6762 YesY
UNII 19V2PL39NG YesY
KEGG D07444 N
ChEBI CHEBI:4530 YesY
ChEMBL CHEMBL1194666 N
Synonyms Diethylpropion
Chemical data
Formula C13H19NO
Molar mass 205.30 g/mol
Chirality 1 : 1 mixture (racemate)
 NYesY (what is this?)  (verify)

Amfepramone (INN)[note 1] is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant.[2][3] It is used in the short-term management of obesity, along with dietary and lifestyle changes.[2] Amfepramone is most closely chemically related 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.[4]

Pharmacology

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[5] 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.[5] As a result, ethcathinone and amfepramone can essentially be considered a member of the class of drugs known as norepinephrine releasing agents (NRAs).

Abuse

Amfepramone is believed to have relatively low abuse potential.[6][7][8][9] but recently there have been reports of teens and adults in the UK abusing this drug, known as "tombstones" to the abusers.

Legality

Amfepramone is classified as a Schedule IV controlled substance in the United States. It is also a Schedule IV controlled substance in Canada. In the UK Amfepramone is a class C drug [10] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.

Chemistry

  1. Propiophenone is brominated to produce α-bromopropiophenone.
  2. This is reacted with diethylamine to yield the product, diethylpropion.[11][12]

See also

Notes

  1. ↑ Another medically-utilized name is diethylpropion (BAN and 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.

References

  1. 1 2 "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
  2. 1 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: 42.
  4. ↑ Arias, HR; Santamaría, A; Ali, SF (2009). "Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion.". International Review of Neurobiology 88: 223–55. doi:10.1016/S0074-7742(09)88009-4. PMID 19897080.
  5. 1 2 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.
  6. ↑ Cohen, S (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.
  7. ↑ 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.
  8. ↑ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health.
  9. ↑ Caplan, J (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal 88: 943–944. PMC 1921278. PMID 14018413.
  10. ↑ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation.
  11. ↑ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke
  12. ↑ 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.
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