펜에틸아민

펜에틸아민
체계적 명칭 (IUPAC 명명법)
	2-Phenylethan-1-amine
식별 정보
CAS 등록번호	64-04-0
ATC 코드	none
PubChem	1001
드러그뱅크	DB04325
ChemSpider	13856352
화학적 성질
화학식	C8H11N
분자량	121.18 g/mol
SMILES	eMolecules & PubChem
유의어	PEA; phenylethylamine
물리적 성질
밀도	0.9640 g/cm³
녹는점	-60 °C (-76 °F)
끓는점	195 °C (383 °F)
약동학 정보
생체적합성	?
동등생물의약품	?
약물 대사	Primarily: MAO-B; Other enzymes: MAO-A, SSAOs (AOC2 & AOC3), PNMT, AANAT, FMO3, and others
생물학적 반감기	Exogenous: 5–10 minutes; Endogenous: ~30 seconds;
배출	Renal (kidneys)
처방 주의사항
임부투여안전성	?
법적 상태	AU: Unscheduled; CA: Unscheduled; UK: Unscheduled; US: Unscheduled; UN: Unscheduled;
중독 경향	Psychological: low–moderate; Physical: none
투여 방법	Oral (taken by mouth)

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.

치환된 페네틸아민

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.

같이 보기

도파민

각주

↑ ^가 ^나 〈Chemical and Physical Properties〉. 《Phenethylamine》. 《PubChem Compound》. United States National Library of Medicine – National Center for Biotechnology Information.
↑ ^가 ^나 ^다 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].
↑ ^가 ^나 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
↑ ^가 ^나 ^다 ^라 ^마 〈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 문헌

[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

외부 링크

Phenethylamine MS Spectrum

[Pubchem-1] 가 ^나 〈Chemical and Physical Properties〉. 《Phenethylamine》. 《PubChem Compound》. United States National Library of Medicine – National Center for Biotechnology Information.

[Renaissance-2] 가 ^나 ^다 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].

[Vascular-3] 가 ^나 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

[HMDB_PEA-4] 가 ^나 ^다 ^라 ^마 〈Phenylethylamine〉. 《HMDB Version 3.6》. Human Metabolome Database. 2016년 2월 11일. 2016년 9월 20일에 확인함.

[PEA_MAO-A_and_B_Substrate-Suzuki-5] 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.

[SSAO-6] 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.

[FMO-7] 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).

[FMO3_catecholamines-8] 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].

[Pubchem_exogenous_half-life-9] 〈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.

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