4-甲基苯丙胺

4-甲基苯丙胺
臨床資料
其他名稱	4-甲基安非他命; 对甲基苯丙胺; 对甲基安非他命;
给药途径	口服、鼻内、注射
ATC碼	未分配;
法律規範狀態
法律規範	加：Schedule I; 德：Anlage II; 英：Class A; 美：Schedule II (isomer of Methamphetamine);
藥物動力學數據
生物半衰期	6-12 hours
排泄途徑	Urine
识别信息
	IUPAC命名法 1-(4-methylphenyl)propan-2-amine; ;
CAS号	64-11-9
PubChem CID	199116;
ChemSpider	172349 ;
UNII	9E273KL7HS;
ChEMBL	ChEMBL166183 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID50945351 ;
化学信息
化学式	C10H15N
摩尔质量	149.24 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES NC(Cc1ccc(cc1)C)C;
	InChI InChI=1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 ; Key:ZDHZDWSHLNBTEB-UHFFFAOYSA-N ;

4-甲基苯丙胺（英语：4-Methylamphetamine，简称4-MA），也叫4-甲基安非他命，是苯乙胺和苯丙胺化学类别的兴奋剂和降食欲剂。

在体外，它作为一种有效且平衡的血清素、去甲肾上腺素和多巴胺释放剂，对血清素、去甲肾上腺素和多巴胺转运蛋白的K_i 亲和力值分别为53.4nM、22.2nM和44.1nM。^[1]然而，最近涉及对大鼠进行微透析的体内研究显示出不同的趋势。这些研究表明，相对于多巴胺（~5x基线），4-甲基苯丙胺在提高血清素（~18x基线）方面更有效。作者推测这是因为5-HT通过某种机制抑制了多巴胺能释放。例如，有人提出这可能是5HT_2C受体的激活，因为已知这会抑制多巴胺能释放。此外还有其他解释，例如5-HT释放然后继续促进GABA释放，这对多巴胺能神经元有抑制作用。^[2]

4-甲基苯丙胺在1952年作为一种食欲抑制剂进行了研究，甚至被赋予了商品名Aptrol，但开发显然从未完成。^[3]最近，它被报道为一种新型狡诈家药物。

在动物研究中，4-甲基苯丙胺被证明在一系列测试的类似药物（其他药物为3-甲基苯丙胺、4-氟苯丙胺和3-氟苯丙胺）中自我给药率最低，这可能是由于相对于多巴胺，释放血清素的效力最高。^[4]^[5]

2012年至2013年，整个欧洲报告有十几人因食用受4-甲基苯丙胺污染的苯丙胺而死亡。^[6]

参见

参考资料

^ Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL. Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. The Journal of Pharmacology and Experimental Therapeutics. May 2005, 313 (2): 848–54. PMID 15677348. S2CID 12135483. doi:10.1124/jpet.104.080101.
^ Di Giovanni G, Esposito E, Di Matteo V. Role of serotonin in central dopamine dysfunction (PDF). CNS Neuroscience & Therapeutics. June 2010, 16 (3): 179–94 [2023-02-22]. PMC 6493878 . PMID 20557570. doi:10.1111/j.1755-5949.2010.00135.x. （原始内容存档 (PDF)于2023-06-01）.
^ Gelvin EP, McGAVACK TH. 2-Amino-1-(p-methylphenyl)-propane (aptrol) as an anorexigenic agent in weight reduction. New York State Journal of Medicine. January 1952, 52 (2): 223–6. PMID 14890975.
^ Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL. Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. The Journal of Pharmacology and Experimental Therapeutics. May 2005, 313 (2): 848–54. PMID 15677348. S2CID 12135483. doi:10.1124/jpet.104.080101.
^ Baumann MH, Clark RD, Woolverton WL, Wee S, Blough BE, Rothman RB. In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat. The Journal of Pharmacology and Experimental Therapeutics. April 2011, 337 (1): 218–25. PMC 3063744 . PMID 21228061. doi:10.1124/jpet.110.176271.
^ Blanckaert P, van Amsterdam J, Brunt T, van den Berg J, Van Durme F, Maudens K, van Bussel J. 4-Methyl-amphetamine: a health threat for recreational amphetamine users. Journal of Psychopharmacology. September 2013, 27 (9): 817–22. PMID 23784740. S2CID 35436194. doi:10.1177/0269881113487950.

[pmid15677348-1] Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL. Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. The Journal of Pharmacology and Experimental Therapeutics. May 2005, 313 (2): 848–54. PMID 15677348. S2CID 12135483. doi:10.1124/jpet.104.080101.

[2] Di Giovanni G, Esposito E, Di Matteo V. Role of serotonin in central dopamine dysfunction (PDF). CNS Neuroscience & Therapeutics. June 2010, 16 (3): 179–94 [2023-02-22]. PMC 6493878 . PMID 20557570. doi:10.1111/j.1755-5949.2010.00135.x. （原始内容存档 (PDF)于2023-06-01）.

[pmid14890975-3] Gelvin EP, McGAVACK TH. 2-Amino-1-(p-methylphenyl)-propane (aptrol) as an anorexigenic agent in weight reduction. New York State Journal of Medicine. January 1952, 52 (2): 223–6. PMID 14890975.

[4] Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL. Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. The Journal of Pharmacology and Experimental Therapeutics. May 2005, 313 (2): 848–54. PMID 15677348. S2CID 12135483. doi:10.1124/jpet.104.080101.

[5] Baumann MH, Clark RD, Woolverton WL, Wee S, Blough BE, Rothman RB. In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat. The Journal of Pharmacology and Experimental Therapeutics. April 2011, 337 (1): 218–25. PMC 3063744 . PMID 21228061. doi:10.1124/jpet.110.176271.

[6] Blanckaert P, van Amsterdam J, Brunt T, van den Berg J, Van Durme F, Maudens K, van Bussel J. 4-Methyl-amphetamine: a health threat for recreational amphetamine users. Journal of Psychopharmacology. September 2013, 27 (9): 817–22. PMID 23784740. S2CID 35436194. doi:10.1177/0269881113487950.

[1]

[2]

[3]

[4]

[5]

[6]