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Amfepramone

Clinical data
Trade names	Tenuate
Other names	Diethylpropion
AHFS/Drugs.com	Monograph
MedlinePlus	a682037
Pregnancy category	B
Routes of administration	Oral
ATC code	A08AA03 (WHO)
Legal status
Legal status	US: Schedule IV
Identifiers
IUPAC name (RS)-2-diethylamino-1-phenylpropan-1-one
CAS Number	134-80-5
PubChem CID	7029
DrugBank	DB00937
ChemSpider	6762
UNII	19V2PL39NG
KEGG	D07444
ChEBI	CHEBI:4530
ChEMBL	ChEMBL1194666
CompTox Dashboard (EPA)	DTXSID6022929
ECHA InfoCard	100.001.836
Chemical and physical data
Formula	C13H19NO
Molar mass	205.30 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(c1ccccc1)C(N(CC)CC)C
InChI 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 Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N
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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.

Pharmacology

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

Abuse

Amfepramone is believed to have relatively low abuse potential.

Legality

Amfepramone is classified as a Schedule IV controlled substance in the United States. In the UK Amfepramone is a class C drug.

Chemistry

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

Reference: U.S. patent 3,001,910 Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01395a032, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/ja01395a032 instead.

See also

• Substituted cathinone

References

1. ^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–59. doi:10.2174/156802606778249766. PMID 17017961.
2. Cohen S (1977). "Diethylpropion (tenuate): an infrequently abused anorectic". Psychosomatics. 18 (1): 28–33. PMID 850721.
3. Jasinski DR, Krishnan S (2009). "Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse". Journal of Psychopharmacology. 23 (4): 419–27. doi:10.1177/0269881109103113. PMID 19329547. {{cite journal}}: Unknown parameter |month= ignored (help)
4. http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1611
5. CAPLAN J (1963). "Habituation to diethylpropion (Tenuate)". Canadian Medical Association Journal. 88: 943–4. PMC 1921278. PMID 14018413. {{cite journal}}: Unknown parameter |month= ignored (help)
6. http://www.statutelaw.gov.uk/content.aspx?LegType=All+Legislation&title=The+Misuse+of+Drugs+Act+1971&searchEnacted=0&extentMatchOnly=0&confersPower=0&blanketAmendment=0&sortAlpha=0&TYPE=QS&PageNumber=1&NavFrom=0&parentActiveTextDocId=1367412&ActiveTextDocId=1367471&filesize=1699

• Anorectics
• Cathinones
• Stimulants