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
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 (WHO)
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
Molecular mass 205.30 g/mol
  • 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 YesY
  • Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N YesY
 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. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke 
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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