間酪胺

間酪胺
	IUPAC名; 3-(2-Aminoethyl)phenol
別名	m-Tyramine; 3-Tyramine;; 3-Hydroxyphenylethylamine
識別
CAS號	588-05-6
PubChem	11492
ChemSpider	11008
SMILES	Oc1cc(ccc1)CCN;
InChI	InChI=1S/C8H11NO/c9-5-4-7-2-1-3-8(10)6-7/h1-3,6,10H,4-5,9H2;
ChEBI	89626
性質
化學式	C8H11NO
摩爾質量	137.18 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

間酪胺（Meta-Tyramine)，或稱3-酪胺，是一種神經調節中的內源性痕量胺。它是苯乙胺的結構類似物，^[1]^[2]^[3]也是對酪胺（即酪胺）的位置異構體。且與對酪胺相似的是，間酪胺也對腎上腺素和多巴胺系統有影響。^[4]^[5]

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間酪胺通過芳香族胺基酸脫羧酶控制的間酪氨酸代謝產生，可通過大腦的CYP2D6酶代謝為多巴胺。^[6]

參見

對酪胺

參考資料

[1]
Biosynthesis of some urinary trace amines in the rat and the human. Research Communications in Chemical Pathology and Pharmacology. November 1981, 34 (2): 295–310. PMID 7335956.
[2]
The in vitro release of endogenous m-tyramine, p-tyramine and dopamine from rat striatum. Neurochemical Research. June 1982, 7 (6): 705–16. PMID 7121718. doi:10.1007/bf00965523.
[3]
The concentration of p- and m-tyramine in the rat mesolimbic system: its regional distribution and effect of monoamine oxidase inhibition. Brain Research. June 1987, 412 (2): 370–4. PMID 3607473. doi:10.1016/0006-8993(87)91145-0.
[4]
The role of catecholamines, 5-hydroxytryptamine and m-tyramine in the behavioural effects of m-tyrosine in the rat. European Journal of Pharmacology. October 1982, 84 (3–4): 139–49. PMID 7173317. doi:10.1016/0014-2999(82)90196-0.
[5]
The effects of administration of meta-tyramine and para-tyramine on dopamine and its metabolites in the rat striatum. Progress in Neuro-psychopharmacology & Biological Psychiatry. 1984, 8 (4–6): 705–9. PMID 6531442. doi:10.1016/0278-5846(84)90042-3.
[6]
The endogenous substrates of brain CYP2D. Eur. J. Pharmacol. February 2014, 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

[pmid7335956-1] [1]
Biosynthesis of some urinary trace amines in the rat and the human. Research Communications in Chemical Pathology and Pharmacology. November 1981, 34 (2): 295–310. PMID 7335956.

[pmid7121718-2] [2]
The in vitro release of endogenous m-tyramine, p-tyramine and dopamine from rat striatum. Neurochemical Research. June 1982, 7 (6): 705–16. PMID 7121718. doi:10.1007/bf00965523.

[pmid3607473-3] [3]
The concentration of p- and m-tyramine in the rat mesolimbic system: its regional distribution and effect of monoamine oxidase inhibition. Brain Research. June 1987, 412 (2): 370–4. PMID 3607473. doi:10.1016/0006-8993(87)91145-0.

[pmid7173317-4] [4]
The role of catecholamines, 5-hydroxytryptamine and m-tyramine in the behavioural effects of m-tyrosine in the rat. European Journal of Pharmacology. October 1982, 84 (3–4): 139–49. PMID 7173317. doi:10.1016/0014-2999(82)90196-0.

[pmid6531442-5] [5]
The effects of administration of meta-tyramine and para-tyramine on dopamine and its metabolites in the rat striatum. Progress in Neuro-psychopharmacology & Biological Psychiatry. 1984, 8 (4–6): 705–9. PMID 6531442. doi:10.1016/0278-5846(84)90042-3.

[CYP2D6_tyramine-dopamine_metabolism-6] [6]
The endogenous substrates of brain CYP2D. Eur. J. Pharmacol. February 2014, 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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