3-甲氧基酪胺

3-甲氧基酪胺
別名	3-甲氧基-4-羥基苯乙胺
識別
CAS號	554-52-9
PubChem	1669
ChemSpider	1606
InChI	1/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3;
InChIKey	DIVQKHQLANKJQO-UHFFFAOYAB
MeSH	3-methoxytyramine
IUPHAR配體	6642
性質
化學式	C9H13NO2
莫耳質量	167.21 g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

3-甲氧基酪胺（3-MT），或稱3-甲氧基-4-羥基苯乙胺，是一種人體痕量胺，是神經遞質多巴胺的代謝產物。^[1]通過兒茶酚-O-甲基轉移酶（COMT）將一個甲基引入多巴胺而形成。3-MT可進一步被單胺氧化酶（MAO）代謝形成高香草酸（HVA），然後隨尿液排出人體。

這種物質最初被認爲是「生理上無活性」，但現時已發現可以作爲人類TAAR1（痕量胺相關受體1）的激動劑。^[1]^[2]

合成

人腦中兒茶酚胺&痕量胺的合成路徑^[3]^[4]^[5]

N-甲基酪胺（英語：N-Methyltyramine）

主要合
成路徑

AAAH（英語：Biopterin-dependent aromatic amino acid hydroxylase）

大腦
CYP2D6

次要
合成
路徑

COMT

DBH

人體中的兒茶酚胺及苯乙胺都是起源自胺基酸

參見

參考文獻

^ ^1.0 ^1.1 The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed. Pharmacother. October 2016, 83: 439–449. PMID 27424325. doi:10.1016/j.biopha.2016.07.002. Khan MZ, Nawaz W (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. PMID 27424325.
^ The dopamine metabolite 3-methoxytyramine is a neuromodulator. PLOS ONE. 2010, 5 (10): e13452. Bibcode:2010PLoSO...513452S. PMC 2956650  . PMID 20976142. doi:10.1371/journal.pone.0013452.
^ Broadley KJ. The vascular effects of trace amines and amphetamines. Pharmacol. Ther. 2010-03, 125 (3): 363–375. PMID 19948186. doi:10.1016/j.pharmthera.2009.11.005.
^ Lindemann L, Hoener MC. A renaissance in trace amines inspired by a novel GPCR family. Trends Pharmacol. Sci. 2005-05, 26 (5): 274–281. PMID 15860375. doi:10.1016/j.tips.2005.03.007.
^ Wang X, Li J, Dong G, Yue J. The endogenous substrates of brain CYP2D. Eur. J. Pharmacol. 2014-02-05, 724: 211–218. PMID 24374199. doi:10.1016/j.ejphar.2013.12.025. The highest level of brain CYP2D activity was found in the substantia nigra ... The in vitro and in vivo studies have shown the contribution of the alternative CYP2D-mediated dopamine synthesis to the concentration of this neurotransmitter although the classic biosynthetic route to dopamine from tyrosine is active. ... Tyramine levels are especially high in the basal ganglia and limbic system, which are thought to be related to individual behavior and emotion (Yu et al., 2003c). ... Rat CYP2D isoforms (2D2/2D4/2D18) are less efficient than human CYP2D6 for the generation of dopamine from p-tyramine. The K_m values of the CYP2D isoforms are as follows: CYP2D6 (87–121 μm) ≈ CYP2D2 ≈ CYP2D18 > CYP2D4 (256 μm) for m-tyramine and CYP2D4 (433 μm) > CYP2D2 ≈ CYP2D6 > CYP2D18 (688 μm) for p-tyramine

[Human_trace_amines_and_hTAARs_October_2016_review-1] 1.0 ^1.1 The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed. Pharmacother. October 2016, 83: 439–449. PMID 27424325. doi:10.1016/j.biopha.2016.07.002. Khan MZ, Nawaz W (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. PMID 27424325.

[pmid20976142-2] The dopamine metabolite 3-methoxytyramine is a neuromodulator. PLOS ONE. 2010, 5 (10): e13452. Bibcode:2010PLoSO...513452S. PMC 2956650  . PMID 20976142. doi:10.1371/journal.pone.0013452.

[Trace_amine_template_1-3] Broadley KJ. The vascular effects of trace amines and amphetamines. Pharmacol. Ther. 2010-03, 125 (3): 363–375. PMID 19948186. doi:10.1016/j.pharmthera.2009.11.005.

[Trace_amine_template_2-4] Lindemann L, Hoener MC. A renaissance in trace amines inspired by a novel GPCR family. Trends Pharmacol. Sci. 2005-05, 26 (5): 274–281. PMID 15860375. doi:10.1016/j.tips.2005.03.007.

[CYP2D6_tyramine-dopamine_metabolism-5] Wang X, Li J, Dong G, Yue J. The endogenous substrates of brain CYP2D. Eur. J. Pharmacol. 2014-02-05, 724: 211–218. PMID 24374199. doi:10.1016/j.ejphar.2013.12.025. The highest level of brain CYP2D activity was found in the substantia nigra ... The in vitro and in vivo studies have shown the contribution of the alternative CYP2D-mediated dopamine synthesis to the concentration of this neurotransmitter although the classic biosynthetic route to dopamine from tyrosine is active. ... Tyramine levels are especially high in the basal ganglia and limbic system, which are thought to be related to individual behavior and emotion (Yu et al., 2003c). ... Rat CYP2D isoforms (2D2/2D4/2D18) are less efficient than human CYP2D6 for the generation of dopamine from p-tyramine. The K_m values of the CYP2D isoforms are as follows: CYP2D6 (87–121 μm) ≈ CYP2D2 ≈ CYP2D18 > CYP2D4 (256 μm) for m-tyramine and CYP2D4 (433 μm) > CYP2D2 ≈ CYP2D6 > CYP2D18 (688 μm) for p-tyramine

[1]

[2]

[3]

[4]

[5]