4-氟麻黃鹼

4-氟麻黃鹼
臨床資料
其他名稱	4-FEP; 4-Fluoro-β-hydroxy-N-methylamphetamine
識別資訊
	IUPAC命名法 (1S,2R)-1-(4-Fluorophenyl)-2-(methylamino)propan-1-ol; ;
CAS號	63009-92-7
PubChem CID	95436263;
ChemSpider	26701426;
UNII	FUH6UKV9U8;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID401024289 ;
化學資訊
化學式	C10H14FNO
摩爾質量	183.23 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	SMILES C[C@H]([C@H](C1=CC=C(C=C1)F)O)NC;
	InChI InChI=1S/C10H14FNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,10,12-13H,1-2H3/t7-,10-/m1/s1; Key:SPEQHEOLWDGWML-GMSGAONNSA-N;

4-氟麻黃鹼（4-FEP）是一種新型精神活性物質，屬於β-羥基苯丙胺衍生物類藥物，為麻黃鹼的化學衍生物之一。^[1]^[2]^[3]

藥理學

與其他苯丙胺衍生物類藥物相似，4-氟麻黃鹼是一種單胺再攝取抑制劑和單胺釋放劑。^[3]^[4]它特別作為去甲腎上腺素釋放劑具有較高選擇性。^[3]^[4]與許多其他苯丙胺類物質不同的是，4-氟麻黃鹼對人類微量胺相關受體 1（hTAAR1）不具有顯著親和力，這一點與大多數卡西酮衍生物相似。^[3]^[4]^[5]

化學

4-氟麻黃鹼，也稱為4-氟-β-羥基-N-甲基苯丙胺（4-fluoro-β-hydroxy-N-methylamphetamine），是一種苯乙胺衍生物、苯丙胺衍生物和β-羥基苯丙胺衍生物。^[6]^[1]它是麻黃鹼的4-氟類似物。^[6]^[1]

4-氟麻黃鹼的化學合成已在文獻中被描述。^[7]此外，它可作為合成4-氟甲基苯丙胺（4-FMA）的前體。^[3]其預測的分配係數（XLogP3）為1.0。^[6]相比之下，麻黃鹼的log P值預測為0.9。^[8]

歷史

4-氟麻黃鹼最早在1991年的科學文獻中被描述。^[7]隨後在2013年被識別為一種「新型精神活性物質」。^[9] 其藥理學特性在2015年被系統研究。^[3]^[4]

其他藥物

4-氟麻黃鹼是4-氟甲卡西酮（4-FMC；氟麻卡酮）代謝過程中形成的一種代謝產物。^[10]^[11]

參考

^ ^1.0 ^1.1 ^1.2 King LA. New phenethylamines in Europe. Drug Test Anal. 2014, 6 (7–8): 808–818. PMID 24574327. doi:10.1002/dta.1570.
^ Corkery JM, Schifano F, Martinotti G. How deaths can help clinicians and policy-makers understand the risks of novel psychoactive substances. Br J Clin Pharmacol. March 2020, 86 (3): 482–498. PMC 7080619 . PMID 31770457. doi:10.1111/bcp.14183.
^ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 ^3.5 Rickli, Anna. Pharmacology of novel psychoactive substances (學位論文). 2016. doi:10.5451/UNIBAS-006616893.
^ ^4.0 ^4.1 ^4.2 ^4.3 Rickli A, Hoener MC, Liechti ME. Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones (PDF). Eur Neuropsychopharmacol. March 2015, 25 (3): 365–376. PMID 25624004. doi:10.1016/j.euroneuro.2014.12.012.
^ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME. In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1. J Pharmacol Exp Ther. April 2016, 357 (1): 134–144. PMID 26791601. doi:10.1124/jpet.115.229765.
^ ^6.0 ^6.1 ^6.2 1-(4-Fluorophenyl)-2-(methylamino)propan-1-ol. PubChem. [12 September 2024].
^ ^7.0 ^7.1 Mullen AJ. The synthesis and pharmacology of ephedrine analogues (學位論文). 1991 [12 September 2024].
^ Ephedrine. PubChem. [12 September 2024].
^ Archer JR, Dargan PI, Chan WL, Hitchings A, Hudson S, Wood DM. 201. Trend analysis of novel psychoactive substances detected in pooled urine samples from street urinals over six months. Clinical Toxicology. 2013, 51 (7).
^ Uralets V, Rana S, Morgan S, Ross W. Testing for designer stimulants: metabolic profiles of 16 synthetic cathinones excreted free in human urine. J Anal Toxicol. June 2014, 38 (5): 233–241. PMID 24668489. doi:10.1093/jat/bku021 .
^ Fan SY, Zang CZ, Shih PH, Ko YC, Hsu YH, Lin MC, Tseng SH, Wang DY. A LC-MS/MS method for determination of 73 synthetic cathinones and related metabolites in urine. Forensic Sci Int. October 2020, 315: 110429. PMID 32784041. doi:10.1016/j.forsciint.2020.110429.

[King2014-1] 1.0 ^1.1 ^1.2 King LA. New phenethylamines in Europe. Drug Test Anal. 2014, 6 (7–8): 808–818. PMID 24574327. doi:10.1002/dta.1570.

[CorkerySchifanoMartinotti2020-2] Corkery JM, Schifano F, Martinotti G. How deaths can help clinicians and policy-makers understand the risks of novel psychoactive substances. Br J Clin Pharmacol. March 2020, 86 (3): 482–498. PMC 7080619 . PMID 31770457. doi:10.1111/bcp.14183.

[Rickli2016-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 ^3.5 Rickli, Anna. Pharmacology of novel psychoactive substances (學位論文). 2016. doi:10.5451/UNIBAS-006616893.

[RickliHoenerLiechti2015-4] 4.0 ^4.1 ^4.2 ^4.3 Rickli A, Hoener MC, Liechti ME. Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones (PDF). Eur Neuropsychopharmacol. March 2015, 25 (3): 365–376. PMID 25624004. doi:10.1016/j.euroneuro.2014.12.012.

[SimmlerBuchyChaboz2016-5] Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME. In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1. J Pharmacol Exp Ther. April 2016, 357 (1): 134–144. PMID 26791601. doi:10.1124/jpet.115.229765.

[PubChem-6] 6.0 ^6.1 ^6.2 1-(4-Fluorophenyl)-2-(methylamino)propan-1-ol. PubChem. [12 September 2024].

[Mullen1991-7] 7.0 ^7.1 Mullen AJ. The synthesis and pharmacology of ephedrine analogues (學位論文). 1991 [12 September 2024].

[PubChem-Ephedrine-8] Ephedrine. PubChem. [12 September 2024].

[ArcherDarganChan2013-9] Archer JR, Dargan PI, Chan WL, Hitchings A, Hudson S, Wood DM. 201. Trend analysis of novel psychoactive substances detected in pooled urine samples from street urinals over six months. Clinical Toxicology. 2013, 51 (7).

[UraletsRanaMorgan2014-10] Uralets V, Rana S, Morgan S, Ross W. Testing for designer stimulants: metabolic profiles of 16 synthetic cathinones excreted free in human urine. J Anal Toxicol. June 2014, 38 (5): 233–241. PMID 24668489. doi:10.1093/jat/bku021 .

[FanZangShih2020-11] Fan SY, Zang CZ, Shih PH, Ko YC, Hsu YH, Lin MC, Tseng SH, Wang DY. A LC-MS/MS method for determination of 73 synthetic cathinones and related metabolites in urine. Forensic Sci Int. October 2020, 315: 110429. PMID 32784041. doi:10.1016/j.forsciint.2020.110429.

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