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; 對甲基苯丙胺; 對甲基安非他命;
給藥途徑	口服、鼻內、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
識別資訊
	IUPAC命名法 1-(4-methylphenyl)propan-2-amine; ;
CAS號	64-11-9
PubChem CID	199116;
ChemSpider	172349 ;
UNII	9E273KL7HS;
ChEMBL	ChEMBL166183 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID50945351 ;
化學資訊
化學式	C10H15N
摩爾質量	149.24 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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（英語：4-Methylamphetamine，簡稱4-MA），也叫4-甲基安非他命，是苯乙胺和苯丙胺化學類別的興奮劑和降食慾劑。

在體外，它作為一種有效且平衡的血清素、去甲腎上腺素和多巴胺釋放劑，對血清素、去甲腎上腺素和多巴胺轉運蛋白的K_i 親和力值分別為53.4nM、22.2nM和44.1nM。^[1]然而，最近涉及對大鼠進行微透析的體內研究顯示出不同的趨勢。這些研究表明，相對於多巴胺（~5x基線），4-甲基苯丙胺在提高血清素（~18x基線）方面更有效。作者推測這是因為5-HT通過某種機制抑制了多巴胺能釋放。例如，有人提出這可能是5HT_2C受體的激活，因為已知這會抑制多巴胺能釋放。此外還有其他解釋，例如5-HT釋放然後繼續促進GABA釋放，這對多巴胺能神經元有抑制作用。^[2]

4-甲基苯丙胺在1952年作為一種食慾抑制劑進行了研究，甚至被賦予了商品名Aptrol，但開發顯然從未完成。^[3]最近，它被報道為一種新型狡詐家藥物。

在動物研究中，4-甲基苯丙胺被證明在一系列測試的類似藥物（其他藥物為3-甲基苯丙胺、4-氟苯丙胺和3-氟苯丙胺）中自我給藥率最低，這可能是由於相對於多巴胺，釋放血清素的效力最高。^[4]^[5]

2012年至2013年，整個歐洲報告有十幾人因食用受4-甲基苯丙胺污染的苯丙胺而死亡。^[6]

參見

參考資料

^ 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. （原始內容存檔 (PDF)於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. （原始內容存檔 (PDF)於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.

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