N-Acetylserotonin

Source: Wikipedia, the free encyclopedia.
N-Acetylserotonin
Names
Preferred IUPAC name
N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]acetamide
Other names
N-Acetyl-5-hydroxytryptamine
N-Acetyl-5-HT
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.013.560 Edit this at Wikidata
IUPHAR/BPS
MeSH N-Acetylserotonin N-Acetylserotonin
UNII
  • InChI=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) checkY
    Key: MVAWJSIDNICKHF-UHFFFAOYSA-N checkY
  • 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)
    Key: MVAWJSIDNICKHF-UHFFFAOYAX
  • CC(=O)NCCC1=CNC2=C1C=C(C=C2)O
Properties
C12H14N2O2
Molar mass 218.256 g·mol−1
Density 1.268 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

N-Acetylserotonin (NAS), also known as normelatonin, is a

TrkB, and having antioxidant
effects.

Biological function

Like melatonin, NAS is an

synthesis of melatonin.[3] NAS is known to have anti-depressant, neurotrophic and cognition-enhancing effects [7][8] and has been proposed to be a target for the treatment of aging-associated cognitive decline and depression [8]

TrkB receptor

NAS has been shown to act as a

TrkB receptor agonist, while serotonin and melatonin do not.[3]
Subchronic and chronic administration of NAS to adult mice induces proliferation of neural progenitor cells (NPC)s, blockage of TrkB abolished this effect suggesting that it is TrkB-dependent.[9] NAS was also found to significantly enhance NPC proliferation in sleep-deprived mice.[9] It is thought that the anti-depressant and neurotrophic effects of NAS are in part due to its role as a TrkB agonist.[7]

Antioxidant properties

NAS acts as a potent antioxidant, 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.[10] NAS has been shown to protect against lipid peroxidation in microsomes and mitochondria.[11] NAS has also been reported to lower resting levels of ROS in peripheral blood lymphocytes and to exhibit anti-oxidant effects against t-butylated hydroperoxide- and diamide-induced ROS.[12] NAS has also been observed to inhibit nitric oxide synthase.[13]

Anti-inflammatory effects

NAS has been reported to have

TNF-alpha in differentiated THP-1-derived human monocytes.[14]

Miscellaneous

NAS may play a role in the antidepressant effects of

animal models of depression.[3]
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

clorgyline.[15][16]

Biochemistry

NAS is produced from serotonin by the enzyme aralkylamine N-acetyltransferase (AANAT) and is converted to melatonin by acetylserotonin O-methyltransferase (ASMT).

NAS is able to penetrate the blood–brain barrier, unlike serotonin.[17]

See also

References

  1. S2CID 22341451
    .
  2. PMID 13784117
    .
  3. ^
    PMID 20133677
    .
  4. PMID 11261588
    .
  5. PMID 10455277
    .
  6. PMID 10381796
    .
  7. ^
    PMID 22585341
    .
  8. ^
    PMID 23185714
    .
  9. ^
    PMID 21555574
    .
  10. S2CID 94273958
    .
  11. S2CID 6974587
    .
  12. S2CID 32077728
    .
  13. PMID 7582541
    .
  14. S2CID 592935
    .
  15. ^
    PMID 10591054
    .
  16. ^
    PMID 9503569
    .
  17. ^ "N-Acetyl Serotonin". DrugBank.
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