N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine
N-acetyl-5-hydroxytryptamine
CAS: 1210-83-9
Molecular Formula: C12H14N2O2
N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine - Names and Identifiers
| Name | N-acetyl-5-hydroxytryptamine |
| Synonyms | N-Acetyl-5-HT Acetylserotonin N-acetyl-5-hydroxytryptamine N-Acetylserotonin, Normelatonin N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine 3-(2-Acetamidoethyl)-5-hydroxyindoleN-Acetylserotonin N-Acetyl-5-hydroxytryptamine,N-Acetylserotonin, Normelatonin |
| CAS | 1210-83-9 |
| EINECS | 214-916-5 |
| InChI | 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) |
N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine - Physico-chemical Properties
| Molecular Formula | C12H14N2O2 |
| Molar Mass | 218.25 |
| Density | 1.268±0.06 g/cm3(Predicted) |
| Melting Point | 120-122 °C (lit.) |
| Boling Point | 556.8±40.0 °C(Predicted) |
| Flash Point | 290.6°C |
| Solubility | ethanol: 50mg/mL |
| Vapor Presure | 5.25E-13mmHg at 25°C |
| Appearance | White to off-white or slightly pink powder |
| Color | white |
| pKa | 10.09±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.651 |
| MDL | MFCD00005656 |
| In vitro study | N-Acetyl-5-hydroxytryptamine (NAS), a precursor of Melatonin, is acetylated from serotonin by AANAT (arylalkylamine N-acetyltransferase). N-acetylserotonin activates TrkB receptor in a circadian rhythm. N-Acetyl-5-hydroxytryptamine swiftly activates TrkB in a circadian manner and exhibits antidepressant effect in a TrkB-dependent manner. N-Acetyl-5-hydroxytryptamine rapidly activates TrkB, but not TrkA or TrkC, in a neurotrophin- and MT3 receptor-independent manner. |
| In vivo study | To explore whether N-Acetyl-5-hydroxytryptamine, can trigger TrkB activation in vivo, TrkB F616A knockin mice are employed, where it has been shown that TrkB F616A activation can be selectively blocked by 1NMPP1, a derivative of kinase inhibitor PP1, leading to TrkB-null phenotypes. To assess whether N-Acetyl-5-hydroxytryptamine can mimic BDNF, cortical neurons from TrkB F616A knockin mice are prepared. In alignment with a previous report, BDNF- and NAS-mediated TrkB phosphorylation are selectively reduced by 1NMPP1 but not by K252a, whereas serotonin or Melatonin had no effect . These findings suggest that NAS strongly provokes both wild-type TrkB and TrkB F616A tyrosine phosphorylation and activation. |
N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29339900 |
N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine - Reference
| Reference Show more | 1. [IF=5.64] Gangzheng Wang et al."Biosynthetic Pathway and the Potential Role of Melatonin at Different Abiotic Stressors and Developmental Stages in Tolypocladium guangdongense."Front Microbiol. 2021; 12: 746141 |
N-Acetyl-5-hydroxy-1H-indole-3-ethaneamine - Reference Information
| biological activity | N-Acetyl-5-hydroxytryptamine (NAS, N-Acetylserotonin, Normelatonin, O-Demethylmelatonin) is a precursor of melatonin and a selective agonist of effective TrkB receptor. |
| Target | Value |
Last Update：2024-04-09 21:54:55
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