Amfepramone

	WikiDoc Resources for Amfepramone
Articles
Most recent articles on Amfepramone Most cited articles on Amfepramone Review articles on Amfepramone Articles on Amfepramone in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Amfepramone Images of Amfepramone Photos of Amfepramone Podcasts & MP3s on Amfepramone Videos on Amfepramone
Evidence Based Medicine
Cochrane Collaboration on Amfepramone Bandolier on Amfepramone TRIP on Amfepramone
Clinical Trials
Ongoing Trials on Amfepramone at Clinical Trials.gov Trial results on Amfepramone Clinical Trials on Amfepramone at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Amfepramone NICE Guidance on Amfepramone NHS PRODIGY Guidance FDA on Amfepramone CDC on Amfepramone
Books
Books on Amfepramone
News
Amfepramone in the news Be alerted to news on Amfepramone News trends on Amfepramone
Commentary
Blogs on Amfepramone
Definitions
Definitions of Amfepramone
Patient Resources / Community
Patient resources on Amfepramone Discussion groups on Amfepramone Patient Handouts on Amfepramone Directions to Hospitals Treating Amfepramone Risk calculators and risk factors for Amfepramone
Healthcare Provider Resources
Symptoms of Amfepramone Causes & Risk Factors for Amfepramone Diagnostic studies for Amfepramone Treatment of Amfepramone
Continuing Medical Education (CME)
CME Programs on Amfepramone
International
Amfepramone en Espanol Amfepramone en Francais
Business
Amfepramone in the Marketplace Patents on Amfepramone
Experimental / Informatics
List of terms related to Amfepramone

Amfepramone
Clinical data
Trade names	Tenuate
Synonyms	Diethylpropion
AHFS/Drugs.com	Monograph
MedlinePlus	a682037
Pregnancy; category	US: B (No risk in non-human studies) ; ;
Routes of; administration	Oral
ATC code	A08AA03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ; UK: Class C ; US: Schedule IV ;
Pharmacokinetic data
Elimination half-life	4-6 hours (metabolites)
Excretion	Urine (>75%)
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 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C13H19NO
Molar mass	205.30 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 ;
(what is this?) (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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. It's not US FDA approved.

Chemistry

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

Notes

↑ 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

↑ ^1.0 ^1.1 "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
↑ ^2.0 ^2.1 Brayfield, A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.
↑ Template:Cite document
↑ 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.
↑ ^5.0 ^5.1 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.
↑ Cohen, S (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.
↑ 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.
↑ "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
↑ Template:Cite doi

Template:Anorectics Template:Catecholaminergics Template:Phenethylamines

[2] 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.

[MHRA-1] 1.0 ^1.1 "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.

[MD-3] 2.0 ^2.1 Brayfield, A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.

[4] Template:Cite document

[5] 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.

[pmid17017961-6] 5.0 ^5.1 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.

[7] Cohen, S (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.

[8] 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.

[9] "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health.

[10] Caplan, J (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal. 88: 943–944. PMC 1921278. PMID 14018413.

[11] "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation.

[12] US patent 3001910, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke

[13] Template:Cite doi

[1]

[note 1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]