3-甲氧基酪胺

3-甲氧基酪胺
别名	3-甲氧基-4-羟基苯乙胺
识别
CAS号	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配体	6642
性质
化学式	C9H13NO2
摩尔质量	167.21 g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

3-甲氧基酪胺（3-MT），或称3-甲氧基-4-羟基苯乙胺，是一种人体痕量胺，是神经递质多巴胺的代谢产物。^[1]通过儿茶酚-O-甲基转移酶（COMT）将一个甲基引入多巴胺而形成。3-MT可进一步被单胺氧化酶（MAO）代谢形成高香草酸（HVA），然后随尿液排出人体。

这种物质最初被认为是“生理上无活性”，但现时已发现可以作为人类TAAR1（痕量胺相关受体1）的激动剂。^[1]^[2]

合成

人脑中儿茶酚胺&痕量胺的合成路径^[3]^[4]^[5]

N-甲基酪胺（英语：N-Methyltyramine）

主要合
成路径

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

大脑
CYP2D6

次要
合成
路径

COMT

DBH

人体中的儿茶酚胺及苯乙胺都是起源自氨基酸

参见

参考文献

^ ^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

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