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Revision as of 13:22, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 453515484 of page N-Acetylserotonin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'ChEBI', 'CASNo').  Latest revision as of 10:25, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:Hydroxyarenes using HotCat 
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{{DISPLAYTITLE:''N''-Acetylserotonin}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 453514473
| Watchedfields = changed
⚫ | verifiedrevid = 462257090
| Name = ''N''-Acetylserotonin | Name = ''N''-Acetylserotonin
| ImageFile = N-Acetylserotonin.png | ImageFile = N-Acetylserotonin.png
| ImageSize = | ImageSize =
| ImageFile2 = N-Acetylserotonin-3D-sticks.png | ImageFile2 = N-Acetylserotonin-3D-sticks.png
| IUPACName = ''N''-acetamide | PIN = ''N''-acetamide
| OtherNames = ''N''-acetyl-5-hydroxytryptamine, ''N''-acetyl-5-HT | OtherNames = ''N''-Acetyl-5-hydroxytryptamine<br />''N''-Acetyl-5-HT
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| IUPHAR_ligand = 5451
| CASNo = <!-- blanked - oldvalue: 1210-83-9 -->
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | ChEMBL = 33103
| CASNo = 1210-83-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P4TO3C82WV
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 33103
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17697 | ChEBI = 17697
| PubChem = 903 | PubChem = 903
| SMILES = CC(=O)NCCC1=CNC2=C1C=C(C=C2)O | DrugBank = DB04275
| SMILES = CC(=O)NCCC1=CNC2=C1C=C(C=C2)O
| MeSHName = ''N''-Acetylserotonin | MeSHName = ''N''-Acetylserotonin
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 879 | ChemSpiderID = 879
| 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) | 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 | InChIKey = MVAWJSIDNICKHF-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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) | StdInChI = 1S/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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MVAWJSIDNICKHF-UHFFFAOYSA-N | StdInChIKey = MVAWJSIDNICKHF-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=12 | H=14 | N=2 | O=2
| Formula = C<sub>12</sub>H<sub>14</sub>N<sub>2</sub>O<sub>2</sub>
⚫ | Appearance =
| MolarMass = 218.252 g/mol
| Density = 1.268 g/mL
⚫ | Appearance =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility =
| Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}

'''''N''-Acetylserotonin''' ('''NAS'''), also known as '''normelatonin''', is a ] chemical ] in the ] production of ] from ].<ref name="pmid13795316">{{cite journal |vauthors=AXELROD J, WEISSBACH H | title = Enzymatic O-methylation of N-acetylserotonin to melatonin | journal = Science | volume = 131 | issue = 3409| page = 1312 |date=April 1960 | pmid = 13795316 | doi = 10.1126/science.131.3409.1312| bibcode = 1960Sci...131.1312A | s2cid = 22341451 }}</ref><ref name="pmid13784117">{{cite journal |vauthors=WEISSBACH H, REDFIELD BG, AXELROD J | title = Biosynthesis of melatonin: enzymic conversion of serotonin to N-acetylserotonin | journal = Biochimica et Biophysica Acta | volume = 43 | pages = 352–3 |date=September 1960 | pmid = 13784117 | doi = 10.1016/0006-3002(60)90453-4}}</ref> It also has ] in its own right, including acting as a ], an ] of the ], and having ] effects.

==Biological function==
Like melatonin, NAS is an ] at the ]s ], ], and ], and may be considered to be a ].<ref name="pmid20133677">{{cite journal |vauthors=Jang SW, Liu X, Pradoldej S, etal | title = N-acetylserotonin activates TrkB receptor in a circadian rhythm | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 107| issue = 8| pages = 3876–81|date=February 2010 | pmid = 20133677 | pmc = 2840510 | doi = 10.1073/pnas.0912531107 | bibcode = 2010PNAS..107.3876J | doi-access = free }}</ref><ref name="pmid11261588">{{cite journal |vauthors=Zhao H, Poon AM, Pang SF | title = Pharmacological characterization, molecular subtyping, and autoradiographic localization of putative melatonin receptors in uterine endometrium of estrous rats | journal = Life Sciences | volume = 66 | issue = 17 | pages = 1581–91 |date=March 2000 | pmid = 11261588 | doi = 10.1016/S0024-3205(00)00478-1}}</ref><ref name="pmid10455277">{{cite journal |vauthors=Nonno R, Pannacci M, Lucini V, Angeloni D, Fraschini F, Stankov BM | title = Ligand efficacy and potency at recombinant human MT2 melatonin receptors: evidence for agonist activity of some mt1-antagonists | journal = ] | volume = 127 | issue = 5 | pages = 1288–94 |date=July 1999 | pmid = 10455277 | pmc = 1566130 | doi = 10.1038/sj.bjp.0702658 }}</ref><ref name="pmid10381796">{{cite journal |vauthors=Paul P, Lahaye C, Delagrange P, Nicolas JP, Canet E, Boutin JA | title = Characterization of 2-iodomelatonin binding sites in Syrian hamster peripheral organs | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 1 | pages = 334–40 |date=July 1999 | pmid = 10381796 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10381796}}</ref> In addition, NAS is distributed in some areas of the ] where serotonin and melatonin are not, suggesting that it may have unique central duties of its own instead of merely functioning as a ] in the ] of melatonin.<ref name="pmid20133677" /> NAS is known to have anti-depressant, neurotrophic and cognition-enhancing effects <ref name="Tosini G. 2012">{{cite journal | author = Tosini G., Ye K. & Iuvone PM | date = 2012 | title = Neuroprotection, neurogenesis, and the sleepy brain | journal = Neuroscientist | volume = 18 | issue = 6 | pages = 645–653 | doi=10.1177/1073858412446634| pmid = 22585341 | pmc = 3422380 }}</ref><ref name="Oxenkrug G. 2012">{{cite journal | author = Oxenkrug G. & Ratner R. | date = 2012 | title = N-acetylserotonin and aging-associated cognitive impairment and depression | journal = Aging Dis | volume = 3 | issue = 4 | pages = 330–338| pmid = 23185714 | pmc = 3501368 }}</ref> and has been proposed to be a target for the treatment of aging-associated cognitive decline and depression <ref name="Oxenkrug G. 2012"/>

===TrkB receptor===
NAS has been shown to act as a ] ] agonist, while serotonin and melatonin do not.<ref name="pmid20133677" /> Subchronic and chronic administration of NAS to adult mice induces proliferation of neural [[Progenitor cell|
progenitor cells]] (NPC)s, blockage of TrkB abolished this effect suggesting that it is TrkB-dependent.<ref name="Sompol">{{cite journal |author1=Sompol P. |author2=Liu X. |author3=Baba K. |author4=Paul KN. |author5=Tosini G. |author6=Iuvone PM. |author7=Ye K. | year = 2011 | title = N-acetylserotonin promotes hippocampal neuroprogenitor cell proliferation in sleep-deprived mice | journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 108 | issue = 21| pages = 8844–9 | doi=10.1073/pnas.1105114108|pmid=21555574 | pmc=3102377|bibcode=2011PNAS..108.8844S |doi-access=free }}</ref> NAS was also found to significantly enhance NPC proliferation in sleep-deprived mice.<ref name="Sompol"/> It is thought that the anti-depressant and neurotrophic effects of NAS are in part due to its role as a TrkB agonist.<ref name="Tosini G. 2012"/>

===Antioxidant properties===
NAS acts as a potent ], NAS effectiveness as an anti-oxidant has been found to be different depending on the experimental model used, it has been described as being between 5 and 20 times more effect than melatonin at protecting against oxidant damage.<ref>{{cite journal | author = Oxenkrug G | year = 2005 | title = Antioxidant effects of N-acetylserotonin: possible mechanisms and clinical implications | journal = Ann. N. Y. Acad. Sci. | volume = 1053 | pages = 334–47 | doi=10.1111/j.1749-6632.2005.tb00042.x| pmid = 16179540 | s2cid = 94273958 }}</ref> NAS has been shown to protect against ] in microsomes and mitochondria.<ref>{{cite journal |author1=Gavazza MB. |author2=Català A. | year = 2004 | title = Protective effect of N-acetyl-serotonin on the nonenzymatic lipid peroxidation in rat testicular microsomes and mitochondria | journal = J. Pineal Res. | volume = 37 | issue = 3| pages = 153–60 | doi=10.1111/j.1600-079x.2004.00150.x|pmid=15357659 |s2cid=6974587 }}</ref> NAS has also been reported to lower resting levels of ] in peripheral blood lymphocytes and to exhibit anti-oxidant effects against t-butylated hydroperoxide- and diamide-induced ROS.<ref>{{cite journal |author1=Wölfler A. |author2=Abuja PM. |author3=Schauenstein K. |author4=Liebmann PM. | year = 1999 | title = N-acetylserotonin is a better extra- and intracellular antioxidant than melatonin | journal = FEBS Lett | volume = 449 | issue = 2–3| pages = 206–10 | doi=10.1016/s0014-5793(99)00435-4|pmid=10338133 |s2cid=32077728 | doi-access= }}</ref> NAS has also been observed to inhibit ].<ref>{{cite journal |author1=Peter Klemm |author2=Markus Hecker |author3=Hannelore Stockhausen |author4=Chin Chen Wu |author5=Christoph Thiemermann | pmid = 7582541 | volume=115 | issue=7 | title=Inhibition by N-acetyl-5-hydroxytryptamine of nitric oxide synthase expression in cultured cells and in the anaesthetized rat. | date=Aug 1995 | journal=Br J Pharmacol | pages=1175–1181 | doi=10.1111/j.1476-5381.1995.tb15021.x | pmc=1908794}}</ref>

===Anti-inflammatory effects===
NAS has been reported to have ] effects. NAS has been shown to inhibit ]-stimulated production of the ] ] in differentiated THP-1-derived human monocytes.<ref>{{cite journal |author1=Perianayagam MC. |author2=Oxenkrug GF. |author3=Jaber BL. | year = 2005 | title = Immune-modulating effects of melatonin, N-acetylserotonin, and N-acetyldopamine | journal = Ann. N. Y. Acad. Sci. | volume = 1053 | pages = 386–93 | doi=10.1111/j.1749-6632.2005.tb00046.x|pmid=16179544 |s2cid=592935 }}</ref>

===Miscellaneous===
NAS may play a role in the antidepressant effects of ]s (SSRIs) and ]s (MAOIs).<ref name="pmid20133677" /> The SSRI ] and the ] ] ] ] AANAT indirectly through ] mechanisms and thereby increase NAS levels after chronic administration, and this correlates with the onset of their antidepressant effects.<ref name="pmid20133677" /><ref name="pmid10591054">{{cite journal | author = Oxenkrug GF | title = Antidepressive and antihypertensive effects of MAO-A inhibition: role of N-acetylserotonin. A review | journal = Neurobiology (Budapest, Hungary) | volume = 7 | issue = 2 | pages = 213–24 | year = 1999 | pmid = 10591054 }}</ref> Furthermore, light exposure inhibits the synthesis of NAS and reduces the antidepressant effects of MAOIs.<ref name="pmid20133677" /> In addition, AANAT ] display significantly greater immobility times versus control mice in ]s of ].<ref name="pmid20133677" /> These data support a potential role for NAS in mood regulation and in antidepressant-induced therapeutic benefits.

Through a currently unidentified mechanism, NAS may be the cause of the ] seen with clinical treatment of MAOIs.<ref name="pmid10591054" /><ref name="pmid9503569">{{cite journal | author = Oxenkrug GF | title = | language = ru | journal = Voprosy Meditsinskoi Khimii | volume = 43 | issue = 6 | pages = 522–6 | year = 1997 | pmid = 9503569 }}</ref> It reduces ] in rodents, and ] (the ] being a major site of NAS and melatonin synthesis) abolishes the ] effects of ].<ref name="pmid10591054" /><ref name="pmid9503569" />

==Biochemistry==
NAS is produced from serotonin by the ] ] (AANAT) and is converted to melatonin by ] (ASMT).

NAS is able to penetrate the ], unlike serotonin.<ref>{{cite web| url = http://www.drugbank.ca/drugs/DB04275 | title = N-Acetyl Serotonin |publisher = DrugBank}}</ref>

==See also==
* ]
* ]
==References==
{{Reflist|32em}}

{{Neurotransmitters}}
{{Neurotransmitter metabolism intermediates}}
{{Antioxidants}}
{{Growth factor receptor modulators}}
{{Melatonin receptor modulators}}
{{Tryptamines}}

{{DEFAULTSORT:Acetylserotonin, N-}}

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