| N-乙酰血清素 (N-Acetylserotonin) | |
|---|---|
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| 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 |
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| InChI |
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| 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-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（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（MT1、MT2和MT3）的激动剂，并且可以被认为是一种神经递质。[3][4][5][6]
最近，NAS已经显示出作为一种有效力的TrkB受体激动剂，而血清素和褪黑激素并没有此种机制。[3]以"TrkB受体"为介导(TrkB-mediated)而产生出强劲的抗抑郁，神经保护(neuroprotection)和神经营养因子等效果。[3]
此外，光线照射抑制NAS的合成、和减少单胺氧化抑制剂的抗抑郁作用。[3]这些数据强烈支持NAS在调节情绪和引起抗抑郁药的治疗效益之作用。
通过目前未知的机制，NAS可能是姿位性低血压的引发因子、且以"单胺氧化抑制剂"(MAOIs)作临床治疗。[7]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]为什么"姿位性低血压"常见与"单胺氧化抑制剂"(MAOIs)一起发生，而不与SSRIs(这两者均增加NAS级别)一起，而这方面并不清楚。
另见
参考文献
- ↑ AXELROD J, WEISSBACH H. Enzymatic O-methylation of N-acetylserotonin to melatonin. Science. 1960-04, 131 (3409): 1312 [2014-01-15]. PMID 13795316. doi:10.1126/science.131.3409.1312.
- ↑ WEISSBACH H, REDFIELD BG, AXELROD J. Biosynthesis of melatonin: enzymic conversion of serotonin to N-acetylserotonin. Biochimica et Biophysica Acta. 1960-09, 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. 2010-02, 107 (8): 3876 [2014-01-15]. PMC 2840510
. PMID 20133677. doi:10.1073/pnas.0912531107.
- ↑ 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. 2000-03, 66 (17): 1581–91 [2014-01-15]. PMID 11261588. doi:10.1016/S0024-3205(00)00478-1.
- ↑ 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. 1999-07, 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. 1999-07, 290 (1): 334–40 [2014-01-15]. PMID 10381796.
- ↑ 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）.