関: amfepramone

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/08/16 17:03:13」(JST)

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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.^[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).

Abuse

Amfepramone is believed to have relatively low abuse potential.^[2]^[3]^[4]^[5]

Legality

Amfepramone is classified as a Schedule IV controlled substance in the United States. In the UK Amfepramone is a class C drug.^[6]

Chemistry

Propiophenone is brominated to produce α-bromopropiophenone.
This is reacted with diethylamine to yield the product, diethylpropion.^[7]^[8]

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. http://www.bentham-direct.org/pages/content.php?CTMC/2006/00000006/00000017/0004R.SGM.
^ Cohen, S. (1977). "Diethylpropion (Tenuate): An Infrequently Abused Anorectic". Psychosomatics 18 (1): 28–33. PMID 850721. http://psy.psychiatryonline.org/cgi/pmidlookup?view=long&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. http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1611.
^ Caplan, J. (May 1963). "Habituation to Diethylpropion (Tenuate)". Canadian Medical Association Journal 88: 943–944. PMC 1921278. PMID 14018413. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1921278.
^ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation. http://www.legislation.gov.uk/ukpga/1971/38/schedule/2.
^ 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. edit

UpToDate Contents

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1. 成人における肥満：薬物療法 obesity in adults drug therapy
2. 肺動脈性肺高血圧症（グループ1）の疫学と発症機序 the epidemiology and pathogenesis of pulmonary arterial hypertension group 1
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English Journal

Six-month efficacy and safety of amfepramone in obese Mexican patients: a double-blinded, randomized, controlled trial.

Soto-Molina H, Pizarro-Castellanos M, Rosado-Pérez J, Rizzoli-Córdoba A, Lara-Padilla E, del Valle-Laisequilla CF, Reyes-García JG.
International journal of clinical pharmacology and therapeutics.Int J Clin Pharmacol Ther.2015 Jul;53(7):541-9. doi: 10.5414/CP202135.
Amfepramone, also known as diethylpropion, is an anorectic drug used for the short-term treatment of obesity; however, its efficacy and safety during periods greater than 3 months has been scarcely studied. To evaluate the 6-month efficacy and safety of amfepramone treatment in obese adult Mexican p
PMID 26073353

D1 and D2 antagonists reverse the effects of appetite suppressants on weight loss, food intake, locomotion, and rebalance spiking inhibition in the rat NAc shell.

Kalyanasundar B1, Perez CI1, Luna A2, Solorio J1, Moreno MG1, Elias D3, Simon SA4, Gutierrez R5.
Journal of neurophysiology.J Neurophysiol.2015 Jul;114(1):585-607. doi: 10.1152/jn.00012.2015. Epub 2015 May 13.
Obesity is a worldwide health problem that has reached epidemic proportions. To ameliorate this problem, one approach is the use of appetite suppressants. These compounds are frequently amphetamine congeners such as diethylpropion (DEP), phentermine (PHEN), and bupropion (BUP), whose effects are med
PMID 25972577

Mechanisms involved in the vasorelaxant effects produced by the acute application of amfepramone in vitro to rat aortic rings.

López-Canales JS1, Lozano-Cuenca J2, Muãoz-Islas E2, Aguilar-Carrasco JC2, López-Canales OA1, López-Mayorga RM1, Castillo-Henkel EF1, Valencia-Hernández I1, Castillo-Henkel C1.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas médicas e biológicas / Sociedade Brasileira de Biofísica ... [et al.].Braz J Med Biol Res.2015 Jun;48(6):537-44. doi: 10.1590/1414-431X20144261. Epub 2015 Mar 27.
Amfepramone (diethylpropion) is an appetite-suppressant drug used for the treatment of overweight and obesity. It has been suggested that the systemic and central activity of amfepramone produces cardiovascular effects such as transient ischemic attacks and primary pulmonary hypertension. However, i
PMID 25831200

Japanese Journal

中枢性モノアミン制御系

日本薬理学雑誌 118(5), 303-308, 2001-11-01
NAID 10007943729

肥胖症の新しい治療剤Diethylpropion

産婦人科治療 2(5), ????, 1961-05
NAID 40017827029

「ジエチルプロピオン」

Amfepramone
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
	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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