N-乙酰血清素

N-乙酰血清素
	IUPAC名; N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
英文名	N-Acetylserotonin
别名	NAS
识别
CAS号	1210-83-9
PubChem	903
ChemSpider	879
SMILES	CC(=O)NCCC1=CNC2=C1C=C(C=C2)O;
InChI	1/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15);
InChIKey	MVAWJSIDNICKHF-UHFFFAOYAX
ChEBI	17697
MeSH	N-Acetylserotonin N-Acetylserotonin
性质
化学式	C12H14N2O2
摩尔质量	218.252 g·mol⁻¹
密度	1.268 g/mL
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

N-乙酰血清素（英語：N-Acetylserotonin，NAS，也作normelatonin）是一种天然存在的化合物，是从血清素到褪黑素的内源性合成的反应中间体^[1]^[2]。它由血清素（又称为5-羟色胺）在N-乙酰基转移酶（AANAT）催化下与乙酰辅酶A反应产生，然后N-乙酰血清素再在乙酰血清素O-甲基转移酶（英语：Acetylserotonin O-methyltransferase）（ASMT）催化下被S-腺苷甲硫氨酸甲基化为褪黑素。和褪黑素一样，N-乙酰血清素也是褪黑素受体（英语：melatonin receptor）（MT₁（英语：Melatonin receptor 1A）、MT₂（英语：Melatonin receptor 1B）和MT₃（英语：Melatonin receptor 1C））的激动剂，並且可以被認為是一種神经递质。^[3]^[4]^[5]^[6]

最近，NAS已經顯示出作為一種有效力的TrkB受體激動劑，而血清素和褪黑激素並沒有此種機制。^[3] 以"TrkB受體"為介導(TrkB-mediated)而產生出強勁的抗抑鬱，神經保護(neuroprotection)和神经营养因子等效果。^[3]

此外，光線照射抑制NAS的合成、和減少單胺氧化抑製劑的抗抑鬱作用。^[3] 這些數據強烈支持NAS在調節情緒和引起抗抑鬱藥的治療效益之作用。

通過目前未知的機制，NAS可能是姿位性低血壓的引發因子、且以"單胺氧化抑製劑"(MAOIs)作臨床治療。^[7]^[8] It reduces blood pressure in rodents, and pinealectomy (the pineal gland being a major site of NAS and melatonin synthesis) abolishes the hypotensive effects of clorgyline.^[7]^[8] 為什麼"姿位性低血壓"常見與"單胺氧化抑製劑"(MAOIs)一起發生，而不與SSRIs(這兩者均增加NAS級別)一起，而這方面並不清楚。

另见[编辑]

参考文献[编辑]

^ AXELROD J, WEISSBACH H. Enzymatic O-methylation of N-acetylserotonin to melatonin. Science. April 1960, 131 (3409): 1312 [2014-01-15]. PMID 13795316. doi:10.1126/science.131.3409.1312. （原始内容存档于2019-10-18）.
^ WEISSBACH H, REDFIELD BG, AXELROD J. Biosynthesis of melatonin: enzymic conversion of serotonin to N-acetylserotonin. Biochimica et Biophysica Acta. September 1960, 43: 352–3. PMID 13784117. doi:10.1016/0006-3002(60)90453-4.
^ ^3.0 ^3.1 ^3.2 ^3.3 Jang SW, Liu X, Pradoldej S; et al. N-acetylserotonin activates TrkB receptor in a circadian rhythm. Proceedings of the National Academy of Sciences of the United States of America. February 2010, 107 (8): 3876 [2014-01-15]. PMC 2840510 . PMID 20133677. doi:10.1073/pnas.0912531107. （原始内容存档于2019-10-18）.
^ Zhao H, Poon AM, Pang SF. Pharmacological characterization, molecular subtyping, and autoradiographic localization of putative melatonin receptors in uterine endometrium of estrous rats. Life Sciences. March 2000, 66 (17): 1581–91 [2014-01-15]. PMID 11261588. doi:10.1016/S0024-3205(00)00478-1. （原始内容存档于2019-01-25）.
^ Nonno R, Pannacci M, Lucini V, Angeloni D, Fraschini F, Stankov BM. Ligand efficacy and potency at recombinant human MT2 melatonin receptors: evidence for agonist activity of some mt1-antagonists. British Journal of Pharmacology. July 1999, 127 (5): 1288–94. PMC 1566130 . PMID 10455277. doi:10.1038/sj.bjp.0702658.
^ Paul P, Lahaye C, Delagrange P, Nicolas JP, Canet E, Boutin JA. Characterization of 2-[125I]iodomelatonin binding sites in Syrian hamster peripheral organs. The Journal of Pharmacology and Experimental Therapeutics. July 1999, 290 (1): 334–40 [2014-01-15]. PMID 10381796. （原始内容存档于2019-12-15）.
^ ^7.0 ^7.1 Oxenkrug GF. [N-acetylserotonin and hypotensive effect of MAO-A inhibitors]. Voprosy Meditsinskoi Khimii. 1997, 43 (6): 522–6. PMID 9503569 （俄语）.
^ ^8.0 ^8.1 引证错误：没有为名为pmid10591054的参考文献提供内容

[pmid13795316-1] AXELROD J, WEISSBACH H. Enzymatic O-methylation of N-acetylserotonin to melatonin. Science. April 1960, 131 (3409): 1312 [2014-01-15]. PMID 13795316. doi:10.1126/science.131.3409.1312. （原始内容存档于2019-10-18）.

[pmid13784117-2] WEISSBACH H, REDFIELD BG, AXELROD J. Biosynthesis of melatonin: enzymic conversion of serotonin to N-acetylserotonin. Biochimica et Biophysica Acta. September 1960, 43: 352–3. PMID 13784117. doi:10.1016/0006-3002(60)90453-4.

[pmid20133677-3] 3.0 ^3.1 ^3.2 ^3.3 Jang SW, Liu X, Pradoldej S; et al. N-acetylserotonin activates TrkB receptor in a circadian rhythm. Proceedings of the National Academy of Sciences of the United States of America. February 2010, 107 (8): 3876 [2014-01-15]. PMC 2840510 . PMID 20133677. doi:10.1073/pnas.0912531107. （原始内容存档于2019-10-18）.

[pmid11261588-4] Zhao H, Poon AM, Pang SF. Pharmacological characterization, molecular subtyping, and autoradiographic localization of putative melatonin receptors in uterine endometrium of estrous rats. Life Sciences. March 2000, 66 (17): 1581–91 [2014-01-15]. PMID 11261588. doi:10.1016/S0024-3205(00)00478-1. （原始内容存档于2019-01-25）.

[pmid10455277-5] Nonno R, Pannacci M, Lucini V, Angeloni D, Fraschini F, Stankov BM. Ligand efficacy and potency at recombinant human MT2 melatonin receptors: evidence for agonist activity of some mt1-antagonists. British Journal of Pharmacology. July 1999, 127 (5): 1288–94. PMC 1566130 . PMID 10455277. doi:10.1038/sj.bjp.0702658.

[pmid10381796-6] Paul P, Lahaye C, Delagrange P, Nicolas JP, Canet E, Boutin JA. Characterization of 2-[125I]iodomelatonin binding sites in Syrian hamster peripheral organs. The Journal of Pharmacology and Experimental Therapeutics. July 1999, 290 (1): 334–40 [2014-01-15]. PMID 10381796. （原始内容存档于2019-12-15）.

[pmid9503569-7] 7.0 ^7.1 Oxenkrug GF. [N-acetylserotonin and hypotensive effect of MAO-A inhibitors]. Voprosy Meditsinskoi Khimii. 1997, 43 (6): 522–6. PMID 9503569 （俄语）.

[pmid10591054-8] 8.0 ^8.1 引证错误：没有为名为pmid10591054的参考文献提供内容

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