펜에틸아민

펜에틸아민(Phenethylamine,PEA) 또는 페네틸아민은 실온에서 무색 액체인 방향성 아민족 물질이다. 페네틸아민 또는 더 적절하게는 치환된 페네틸아민(Substituted phenethylamines)은 페네틸아민을 백본(backbone)으로 포함하는 페네틸아민 유도체 그룹이다. 다시 말해서, 이 화학 부류는 페네틸아민 코어(core) 구조에서 하나 이상의 수소 원자를 치환기로 대체하여 형성된 유도체 화합물을 포함한다. 치환된 페네틸아민 부류에는 모든 치환된 암페타민 및 치환된 메틸렌디옥시펜에틸아민(MDxx,methylenedioxyphenethylamines 또는 Substituted methylenedioxy- phenethylamines)이 포함되며, 특히 공감, 각성, 환각, 식욕 부진, 기관지 확장, 충혈 완화 및 또는 항우울에 관여하여 작용하는 많은 메커니즘에서의 생화학 반응을 포함한다. 주요한 치환된 페네틸아민들로는 도파민(3,4-dihydroxyphenethylamine), 에피네프린(β,3,4-trihydroxy-N-methylphenethylamine), 노르에피네프린(β,3,4-trihydroxyphenethylamine), N,N-디메틸페네필아민(N,N-Dimethylphenethylamine 또는 N,N-DMPEA), 메스암페타민(methamphetamine, methylamphetamine, desoxyephedrine), MDMA(3,4-Methylenedioxymethamphetamine)등 다수가 있다. 도파민 〈Chemical and Physical Properties〉. 《Phenethylamine》. 《PubChem Compound》. United States National Library of Medicine – National Center for Biotechnology Information.  Lindemann L, Hoener MC (2005). “A renaissance in trace amines inspired by a novel GPCR family”. 《Trends Pharmacol. Sci.》 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID 15860375. The pharmacology of TAs might also contribute to a molecular understanding of the well-recognized antidepressant effect of physical exercise [51]. In addition to the various beneficial effects for brain function mainly attributed to an upregulation of peptide growth factors [52,53], exercise induces a rapidly enhanced excretion of the main β-PEA metabolite β-phenylacetic acid (b-PAA) by on average 77%, compared with resting control subjects [54], which mirrors increased β-PEA synthesis in view of its limited endogenous pool half-life of ~30 s [18,55].  Broadley KJ (March 2010). “The vascular effects of trace amines and amphetamines”. 《Pharmacol. Ther.》 125 (3): 363–375. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186. Trace amines are metabolized in the mammalian body via monoamine oxidase  〈Phenylethylamine〉. 《HMDB Version 3.6》. Human Metabolome Database. 2016년 2월 11일. 2016년 9월 20일에 확인함.  Suzuki O, Katsumata Y, Oya M (1981). “Oxidation of beta-phenylethylamine by both types of monoamine oxidase: examination of enzymes in brain and liver mitochondria of eight species”. 《J. Neurochem.》 36 (3): 1298–301. doi:10.1111/j.1471-4159.1981.tb01734.x. PMID 7205271.  Kaitaniemi, S; Elovaara, H; Grön, K; Kidron, H; Liukkonen, J; Salminen, T; Salmi, M; Jalkanen, S; Elima, K (2009). “The unique substrate specificity of human AOC2, a semicarbazide-sensitive amine oxidase”. 《Cell. Mol. Life Sci.》 66 (16): 2743–57. doi:10.1007/s00018-009-0076-5. PMID 19588076. The preferred in vitro substrates of AOC2 were found to be 2-phenylethylamine, tryptamine and p-tyramine instead of methylamine and benzylamine, the favored substrates of AOC3.  Krueger SK, Williams DE; Williams (June 2005). “Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism”. 《Pharmacol. Ther.》 106 (3): 357–387. doi:10.1016/j.pharmthera.2005.01.001. PMC 1828602. PMID 15922018. The biogenic amines, phenethylamine and tyramine, are N-oxygenated by FMO to produce the N-hydroxy metabolite, followed by a rapid second oxygenation to produce the trans-oximes (Lin & Cashman, 1997a, 1997b). This stereoselective N-oxygenation to the trans-oxime is also seen in the FMO-dependent N-oxygenation of amphetamine (Cashman et al., 1999) ... Interestingly, FMO2, which very efficiently N-oxygenates N-dodecylamine, is a poor catalyst of phenethylamine N-oxygenation. The most efficient human FMO in phenethylamine N-oxygenation is FMO3, the major FMO present in adult human liver; the Km is between 90 and 200 μM (Lin & Cashman, 1997b).  Robinson-Cohen C, Newitt R, Shen DD, Rettie AE, Kestenbaum BR, Himmelfarb J, Yeung CK (August 2016). “Association of FMO3 Variants and Trimethylamine N-Oxide Concentration, Disease Progression, and Mortality in CKD Patients”. 《PLoS ONE》 11 (8): e0161074. doi:10.1371/journal.pone.0161074. PMC 4981377. PMID 27513517. TMAO is generated from trimethylamine (TMA) via metabolism by hepatic flavin-containing monooxygenase isoform 3 (FMO3). ... FMO3 catalyzes the oxidation of catecholamine or catecholamine-releasing vasopressors, including tyramine, phenylethylamine, adrenaline, and noradrenaline [32, 33].  〈Pharmacology and Biochemistry〉. 《Phenethylamine》. 《PubChem Compound》. United States National Library of Medicine – National Center for Biotechnology Information. Plasma Pharmacokinetics of PEA Could Be Described By 1st-Order Kinetics With Estimated T/2 of Approx 5-10 Min.  [참고] (페네틸아민 유도체의 구조적 특성에 관한 이론적 연구 Theoretical Study on Structural Properties of Phenthylamine Derivatives ,국제문화기술진흥원 , The Journal of the Convergence on Culture Technology (JCCT) KCI 등재 Vol.6 No.4 (2020.11) pp.761-766 이철재 URL) https://www.earticle.net/Article/A386414 Phenethylamine MS Spectrum