安非拉酮

安非拉酮
临床资料
商品名（英语：Drug nomenclature）	Tenuate、Tepanil、Nobesine和其它
其他名称	二乙胺苯酮、二乙胺苯丙酮、二乙基卡西酮
AHFS/Drugs.com	Monograph
MedlinePlus	a682037
核准状况	美 DailyMed: Diethylpropion;
怀孕分级	澳: B2 ; ;
给药途径	口服
ATC码	A08AA03 (WHO) ;
法律规范状态
法律规范	澳：限医生处方（S4）; 加：Schedule G (CDSA IV); 德：Prescription only (Anlage III for higher doses); 欧：Rx-only; 英：Class C; 美：附表IV;
药物动力学数据
生物半衰期	4-6小时 (代谢物)
排泄途径	尿液 (>75%)
识别信息
	IUPAC命名法 (RS)-2-diethylamino-1-phenylpropan-1-one; ;
CAS号	134-80-5
PubChem CID	7029;
IUPHAR/BPS	7161;
DrugBank	DB00937 ;
ChemSpider	6762 ;
UNII	19V2PL39NG;
KEGG	D07444 ;
ChEBI	CHEBI:4530 ;
ChEMBL	ChEMBL1194666 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID6022929 ;
ECHA InfoCard	100.001.836
化学信息
化学式	C13H19NO
摩尔质量	205.30 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
手性	外消旋体
	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 ;

安非拉酮（英语：Amfepramone）是苯乙胺、苯丙胺和卡西酮类的兴奋剂药物，用作食欲抑制剂。^[7]^[8]它用于肥胖的短期管理，以及饮食和生活方式的改变。^[7]安非拉酮与抗抑郁药和戒烟助剂安非他酮在化学上的关系最密切，安非他酮与纳曲酮组合后也被开发为减肥药。^[9]

药理学

安非拉酮本身对单胺转运蛋白没有任何亲和力，而是作为乙卡西酮的前药发挥作用。^[10]乙卡西酮（包括安非拉酮）是一种非常弱的多巴胺能和血清素能，相比之下，去甲肾上腺素的作用分别强大约10倍和20倍。^[10]因此，乙卡西酮和安非拉酮基本上可以被认为是被称为去甲肾上腺素释放剂的一类药物的成员。

化学

安非拉酮可由苯丙酮通过溴化反应合成，然后与二乙胺反应。^[11]^[12]

社会与文化

名称

另一个医学上使用的名称是二乙胺苯酮（Diethylpropion，BAN和ANN）。化学名称包括：α-甲基-β-酮基-N,N-二乙基苯乙胺、N,N-二乙基-β-酮苯丙胺和N,N-二乙基卡西酮。商品名包括：Anorex、Linea、Nobesine、Prefamone、Regenon、Tepanil和Tenuate。

法律地位

安非拉酮在美国被归类为附表IV受管制物质。在英国，安非拉酮是一种 C 类药物，^[13]作为一种药物，它是一种需要安全保管的附表3管制药物。

自2022年6月起，欧洲药品管理局安全委员会建议撤销安非拉酮的上市许可。^[14]^[5]

在中国，安非拉酮是一类管制精神药品，禁止进境^[15]

1999年5月13日，中国国家药品监督管理局撤销了中国卫生部在1993年唯一批准的生产安非拉酮的单位山东潍坊制药二厂的安非拉酮的批准文号^[16]

娱乐用途

几项安非拉酮研究的作者声称，该物质引起使用者成瘾的可能性相对较低。^[17]^[18]^[3]^[19]

参考资料

^ Tenuate Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始内容存档于4 August 2022）.
^ Nobesine Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始内容存档于4 August 2022）.
^ ^3.0 ^3.1 Tepanil (diethylpropion hydrochloride) tablet, extended release. Dailymed. National Institutes of Health. [4 August 2022]. （原始内容存档于8 May 2021）.
^ https://www.ema.europa.eu/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf 互联网档案馆的存档，存档日期27 August 2021. ^[裸网址]
^ ^5.0 ^5.1 Amfepramone-containing medicinal products. European Medicines Agency (EMA). 12 February 2021 [12 February 2021]. （原始内容存档于7 March 2021）.
^ ^6.0 ^6.1 SPC-DOC_PL 16133-0001 (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011 [18 July 2014]. ^{[永久失效链接]}
^ ^7.0 ^7.1 Brayfield A (编). Diethylpropion Hydrochloride. Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 30 January 2013 [18 July 2014]. （原始内容存档于27 August 2021）.
^ TGA Approved Terminology for Medicines, Section 1 – Chemical Substances (PDF). Therapeutic Goods Administration (Tga) (Therapeutic Goods Administration, Department of Health and Ageing, Australian Government). July 1999: 42 [18 July 2014]. （原始内容存档 (PDF)于11 February 2014）.
^ Arias HR, Santamaría A, Ali SF. Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. New Concepts of Psychostimulant Induced Neurotoxicity. International Review of Neurobiology 88. 2009: 223–55. ISBN 9780123745040. PMID 19897080. doi:10.1016/S0074-7742(09)88009-4.
^ ^10.0 ^10.1 Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Current Topics in Medicinal Chemistry. 2006, 6 (17): 1845–59 [7 September 2020]. PMID 17017961. doi:10.2174/156802606778249766. （原始内容存档于23 October 2020）.
^ US patent 3001910,Schutte J,“Anorexigenic Propiophenones”,发行于1961-09-26,指定于Temmler-Werke
^ Hyde JF, Browning E, Adams R. Synthetic Homologs of d,l-Ephedrine. Journal of the American Chemical Society. 1928, 50 (8): 2287–2292. doi:10.1021/ja01395a032.
^ Class C Drugs. Schedule 2 Controlled Drugs. UK Legislation. [7 February 2012]. （原始内容存档于14 November 2012）.
^ EMA recommends withdrawal of marketing authorisation for amfepramone medicines. European Medicines Agency (EMA). 10 June 2022 [10 June 2022]. （原始内容存档于10 June 2022）.
^ 苏州海关在邮包中查获一类管制精神药品安非拉酮. 中华人民共和国南京海关.
^ 国家药品监督管理局关于撤销安非拉酮批准文号的通知
^ Cohen S. Diethylpropion (tenuate): an infrequently abused anorectic. Psychosomatics. 1977, 18 (1): 28–33. PMID 850721. doi:10.1016/S0033-3182(77)71101-6  .
^ Jasinski DR, Krishnan S. Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. Journal of Psychopharmacology. June 2009, 23 (4): 419–27. PMID 19329547. S2CID 6138292. doi:10.1177/0269881109103113.
^ Caplan J. Habituation to diethylpropion (Tenuate). Canadian Medical Association Journal. May 1963, 88: 943–4. PMC 1921278  . PMID 14018413.

外部链接

Amfepramone. Drug Information Portal. U.S. National Library of Medicine. [2023-02-23]. （原始内容存档于2022-09-20）.

[1] Tenuate Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始内容存档于4 August 2022）.

[2] Nobesine Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始内容存档于4 August 2022）.

[Tepanil_FDA_label-3] 3.0 ^3.1 Tepanil (diethylpropion hydrochloride) tablet, extended release. Dailymed. National Institutes of Health. [4 August 2022]. （原始内容存档于8 May 2021）.

[4] ttps://www.ema.europa.eu/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf 互联网档案馆的存档，存档日期27 August 2021. ^[裸网址]

[EU_Amfepramone-5] 5.0 ^5.1 Amfepramone-containing medicinal products. European Medicines Agency (EMA). 12 February 2021 [12 February 2021]. （原始内容存档于7 March 2021）.

[MHRA-6] 6.0 ^6.1 SPC-DOC_PL 16133-0001 (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011 [18 July 2014]. ^{[永久失效链接]}

[MD-7] 7.0 ^7.1 Brayfield A (编). Diethylpropion Hydrochloride. Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 30 January 2013 [18 July 2014]. （原始内容存档于27 August 2021）.

[8] TGA Approved Terminology for Medicines, Section 1 – Chemical Substances (PDF). Therapeutic Goods Administration (Tga) (Therapeutic Goods Administration, Department of Health and Ageing, Australian Government). July 1999: 42 [18 July 2014]. （原始内容存档 (PDF)于11 February 2014）.

[9] Arias HR, Santamaría A, Ali SF. Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. New Concepts of Psychostimulant Induced Neurotoxicity. International Review of Neurobiology 88. 2009: 223–55. ISBN 9780123745040. PMID 19897080. doi:10.1016/S0074-7742(09)88009-4.

[pmid17017961-10] 10.0 ^10.1 Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Current Topics in Medicinal Chemistry. 2006, 6 (17): 1845–59 [7 September 2020]. PMID 17017961. doi:10.2174/156802606778249766. （原始内容存档于23 October 2020）.

[11] US patent 3001910,Schutte J,“Anorexigenic Propiophenones”,发行于1961-09-26,指定于Temmler-Werke

[12] Hyde JF, Browning E, Adams R. Synthetic Homologs of d,l-Ephedrine. Journal of the American Chemical Society. 1928, 50 (8): 2287–2292. doi:10.1021/ja01395a032.

[13] Class C Drugs. Schedule 2 Controlled Drugs. UK Legislation. [7 February 2012]. （原始内容存档于14 November 2012）.

[14] EMA recommends withdrawal of marketing authorisation for amfepramone medicines. European Medicines Agency (EMA). 10 June 2022 [10 June 2022]. （原始内容存档于10 June 2022）.

[15] 苏州海关在邮包中查获一类管制精神药品安非拉酮. 中华人民共和国南京海关.

[16] 国家药品监督管理局关于撤销安非拉酮批准文号的通知

[17] Cohen S. Diethylpropion (tenuate): an infrequently abused anorectic. Psychosomatics. 1977, 18 (1): 28–33. PMID 850721. doi:10.1016/S0033-3182(77)71101-6  .

[18] Jasinski DR, Krishnan S. Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. Journal of Psychopharmacology. June 2009, 23 (4): 419–27. PMID 19329547. S2CID 6138292. doi:10.1177/0269881109103113.

[19] Caplan J. Habituation to diethylpropion (Tenuate). Canadian Medical Association Journal. May 1963, 88: 943–4. PMC 1921278  . PMID 14018413.

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