Amfepramone
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| Systematic (IUPAC) name | |
| (RS)-2-diethylamino-1-phenylpropan-1-one | |
| Clinical data | |
| Trade names | Tenuate |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682037 |
| Pregnancy cat. | B |
| Legal status | Schedule IV (US) |
| Routes | Oral |
| Identifiers | |
| CAS number | 134-80-5  |
| ATC code | A08AA03 |
| PubChem | CID 7029 |
| DrugBank | DB00937 |
| ChemSpider | 6762 |
| UNII | 19V2PL39NG |
| KEGG | D07444  |
| ChEBI | CHEBI:4530 |
| ChEMBL | CHEMBL1194666 |
| Synonyms | Diethylpropion |
| Chemical data | |
| Formula | C13H19NO |
| Mol. mass | 205.30 g/mol |
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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.
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[edit] Pharmacology
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 selective norepinephrine releasing agents (NRAs).
[edit] Abuse
Amfepramone is believed to have relatively low abuse potential.[2][3][4][5]
[edit] Legality
Amfepramone is classified as a Schedule IV controlled substance in the United States. In the UK Amfepramone is a class C drug.[6]
[edit] Chemistry
- Propiophenone is brominated to produce α-bromopropiophenone.
- This is reacted with diethylamine to yield the product, diethylpropion.[7][8]
[edit] See also
[edit] References
- ^ 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.
- ^ Cohen, S. (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics 18 (1): 28–33. PMID 850721.
- ^ 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.
- ^ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health.
- ^ Caplan, J. (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal 88: 943–944. PMC 1921278. PMID 14018413.
- ^ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation.
- ^ US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke
- ^ 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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