4-氟派醋甲酯

4-氟派醋甲酯
識別資訊
	IUPAC命名法 Methyl 2-(4-fluorophenyl)-2-(piperidin-2-yl)acetate; ;
CAS號	1354631-33-6
PubChem CID	70876096;
ChemSpider	26350585 ;
UNII	TN2LV2C0X9;
化學資訊
化學式	C14H18FNO2
摩爾質量	251.30 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
熔點	222.0 °C（431.6 °F）
	SMILES FC1=CC=C(C=C1)C(C(=O)OC)C2CCCCN2;
	InChI InChI=1S/C14H18FNO2/c1-18-14(17)13(12-4-2-3-9-16-12)10-5-7-11(15)8-6-10/h5-8,12-13,16H,2-4,9H2,1H3; Key:XISBAJBPDVRSPG-UHFFFAOYSA-N;

4-氟派醋甲酯 （4-Fluoromethylphenidate），又稱4-FMPH和4F-MPH，是一種能改善使用者的專注力的藥物，與哌醋甲酯相比，是一種效力更強的多巴胺再攝取抑制劑。^[2]^[3]並且由於其藥品帶來的緩和性使得其成癮性與服藥後焦慮更低。

成癮性

4-氟甲基苯甲酸甲酯與其他(±)-threo-甲基苯甲酸甲酯(TMP)類似物一起被進一步研究，以評估其作為抗可卡因藥物的潛力。4F-MPH被報告為具有0.26 (0.18–0.36) mg/kg的ED₅₀，在作為可卡因替代品方面的相對效力為3.33。這是基於其對多巴胺轉運蛋白的結合強度與其作為多巴胺再攝取抑制劑的活性。理論上，這將阻止一些可卡因的效果，而不會像可卡因那樣上癮。^[4] 這被誤解為多巴胺與去甲腎上腺素選擇性比率。

另一項研究發現，在甲基苯甲酸甲酯的threo-異構體中，帶有電子吸引取代基的間位和對位化合物傾向於具有更高的結合效力。含有氟、氯、溴和甲基基團的化合物被報告比甲基苯甲酸甲酯以及密切相關的化合物4F-EPH更有效。4F-MPH被報告具有以下數值：[³H]WIN 35428結合為35.0 ± 3.0 (2) 和 [³H]多巴胺為142 ± 2.0 (2)。

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參考文獻

^ The Drug Enforcement Administration's Special Testing and Research Laboratory Monograph (PDF). February 2017 [2023-10-01]. （原始內容存檔 (PDF)於2022-06-18）.
^ Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR. Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites. Bioorganic & Medicinal Chemistry Letters. April 2004, 14 (7): 1799–802. PMID 15026075. doi:10.1016/j.bmcl.2003.12.097.
^ Misra M, Shi Q, Ye X, Gruszecka-Kowalik E, Bu W, Liu Z, et al. Quantitative structure-activity relationship studies of threo-methylphenidate analogs. Bioorganic & Medicinal Chemistry. October 2010, 18 (20): 7221–38. PMID 20846865. doi:10.1016/j.bmc.2010.08.034.
^ Schweri MM, Deutsch HM, Massey AT, Holtzman SG. Biochemical and behavioral characterization of novel methylphenidate analogs. The Journal of Pharmacology and Experimental Therapeutics. May 2002, 301 (2): 527–35. PMID 11961053. doi:10.1124/jpet.301.2.527.
^ Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM. Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs. Journal of Medicinal Chemistry. March 1996, 39 (6): 1201–9. PMID 8632426. doi:10.1021/jm950697c.

[1] The Drug Enforcement Administration's Special Testing and Research Laboratory Monograph (PDF). February 2017 [2023-10-01]. （原始內容存檔 (PDF)於2022-06-18）.

[2] Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR. Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites. Bioorganic & Medicinal Chemistry Letters. April 2004, 14 (7): 1799–802. PMID 15026075. doi:10.1016/j.bmcl.2003.12.097.

[3] Misra M, Shi Q, Ye X, Gruszecka-Kowalik E, Bu W, Liu Z, et al. Quantitative structure-activity relationship studies of threo-methylphenidate analogs. Bioorganic & Medicinal Chemistry. October 2010, 18 (20): 7221–38. PMID 20846865. doi:10.1016/j.bmc.2010.08.034.

[4] Schweri MM, Deutsch HM, Massey AT, Holtzman SG. Biochemical and behavioral characterization of novel methylphenidate analogs. The Journal of Pharmacology and Experimental Therapeutics. May 2002, 301 (2): 527–35. PMID 11961053. doi:10.1124/jpet.301.2.527.

[5] Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM. Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs. Journal of Medicinal Chemistry. March 1996, 39 (6): 1201–9. PMID 8632426. doi:10.1021/jm950697c.

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