N-Acetyltryptamine

HCID 70547CAS 1016-47-3

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Basic information

Standard SMILES: CC(=O)NCCc1c[nH]c2ccccc12
InChIKey: NVUGEQAEQJTCIX-UHFFFAOYSA-N
Molecular formula: C12H14N2O
Average molar mass: 202.25 g/mol
Monoisotopic mass: 202.11061307

Overview

N-acetyltryptamine is a tryptamine compound having an acetyl substituent attached to the side-chain amino function. It is a member of acetamides and a member of indoles. It is functionally related to a tryptamine.

Names & identifiers

Preferred name: N-Acetyltryptamine
IUPAC: N-[2-(1H-indol-3-yl)ethyl]acetamide
English name: N-ACETYLTRYPTAMINE
Molecular formula: C12H14N2O
Molecular weight: 202.25

Names & synonyms

N-Acetyltryptamine1016-47-3N-(2-(1H-indol-3-yl)ethyl)acetamideN-[2-(1H-Indol-3-yl)ethyl]acetamideCHEBI:55515DTXSID30144042RefChem:927046DTXCID0066533AcetotryptamideAcetamide, N-[2-(1H-indol-3-yl)ethyl]-3-(2-N-Acetylaminoethyl)indoleMFCD00209910

Show more names

N-(2-(1H-Indol-3-yl)N10-AcetyltryptamineAcetyltryptamine, N-TRYPTAMINE, N-ACETYL-N-Acetyltryptamine >N-Acetyltryptamine

Nb-acetyltryptamineN-Acetyl-d3-tryptamineLopac-A-73423-(2-Acetamidoethyl)indoleCHEMBL33171N-[2-(1H-Indol-3-yl)-ethyl]-acetamideMLS001250169ISUPSL100255

Database identifiers

CAS: 1016-47-3
PubChem CID: 70547
DTXSID: DTXSID30144042
ChEMBL: CHEMBL33171
ChEBI: CHEBI:55515
Nikkaji: J99.715C

Properties

Computed structural properties

XLogP: 1.8
Topological polar surface area: 44.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 1
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 230

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

LogP1.41

Physicochemical properties

Melting point: 74 to · 74.0 to 78.0 °C
Boiling point: 200 °C/0.2mmHg · 200°C/0.2mmHg(lit.)
Density: 1.164 · 1.164±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: alcohol: soluble
form: powder
pka: 16.48 · 16.48±0.46(Predicted)
color: White to Light yellow to Light orange
λmax: 290 nm · 290nm(MeOH)(lit.)
CAS DataBase Reference: 1016 · 1016-47-3
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 314 · H314
Precautionary statements: 501 · P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
HS Code: 2933.99 · 2933.99.8290

Safety & regulation

Safety data

wgk: 3
hs_code: 2933.99.8290
Signal word: Danger
Symbol(GHS): GHS05
safety_code: 22-24/25
Hazard statements: H314
Precautionary statements: P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405

Chemistry & industry

Applications · 3 items

DescriptionThe Argentinian medicinal plant Prosopsis nigra contains this alkaloid of the simple indole type which has recently been isolated and characterized. It may be a direct precursor in the biosynthesis of the {:l-carboline bases.

DescriptionN-acetyl Tryptamine is a structural analog of melatonin (5-methoxy-N-acetyltryptamine; ) that binds the melatonin MT2 receptor (Ki = 41 nM). It acts as a melatonin receptor antagonist in frog skin and chicken retina and as a partial agonist in rabbit retina. N-acetyl Tryptamine is also a reaction product of assays for serotonin N-acetyltransferase, the penultimate enzyme in the melatonin biosynthetic pathway.

UsesN-acetyl Tryptamine is a structural analog of melatonin (5-methoxy-N-acetyltryptamine; ) that binds the melatonin MT2 receptor (Ki = 41 nM). It acts as a melatonin receptor antagonist in frog skin and chicken retina and as a partial agonist in rabbit retina. N-acetyl Tryptamine is also a reaction product of assays for serotonin N-acetyltransferase, the penultimate enzyme in the melatonin biosynthetic pathway.