N-乙酰血清素

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N-乙酰血清素
(N-Acetylserotonin)
IUPAC名
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
别名 N-acetyl-5-hydroxytryptamine, N-acetyl-5-HT
识别
CAS号 1210-83-9
PubChem 903
ChemSpider 879
SMILES
InChI
InChIKey MVAWJSIDNICKHF-UHFFFAOYAX
ChEBI 17697
MeSH N-Acetylserotonin N-Acetylserotonin
性质
化学式 C12H14N2O2
摩尔质量 218.252 g/mol g·mol⁻¹
密度 1.268 g/mL
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

N-乙酰血清素英语N-AcetylserotoninNAS,也作normelatonin)是一种天然存在化合物,是从血清素褪黑素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 receptorMT1英语Melatonin receptor 1AMT2英语Melatonin receptor 1BMT3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]

  1. ^ AXELROD J, WEISSBACH H. Enzymatic O-methylation of N-acetylserotonin to melatonin. Science. 1960.April, 131 (3409): 1312. doi:10.1126/science.131.3409.1312. PMID 13795316. 
  2. ^ WEISSBACH H, REDFIELD BG, AXELROD J. Biosynthesis of melatonin: enzymic conversion of serotonin to N-acetylserotonin. Biochimica et Biophysica Acta. 1960.September, 43: 352–3. doi:10.1016/0006-3002(60)90453-4. PMID 13784117. 
  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. 2010.February, 107 (8): 3876. doi:10.1073/pnas.0912531107. PMC 2840510. PMID 20133677. 
  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. 2000.March, 66 (17): 1581–91. doi:10.1016/S0024-3205(00)00478-1. PMID 11261588. 
  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. 1999.July, 127 (5): 1288–94. doi:10.1038/sj.bjp.0702658. PMC 1566130. PMID 10455277. 
  6. ^ Paul P, Lahaye C, Delagrange P, Nicolas JP, Canet E, Boutin JA. Characterization of 2-[125Iiodomelatonin binding sites in Syrian hamster peripheral organs]. The Journal of Pharmacology and Experimental Therapeutics. 1999.July, 290 (1): 334–40. PMID 10381796. 
  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 (Russian). 
  8. ^ 引用错误:无效<ref>标签;未为name属性为pmid10591054的引用提供文字