N-Acetyltryptamine

Base Information

• Chemical Name: N-Acetyltryptamine
• CAS No.: 1016-47-3
• Molecular Formula: C12H14N2O
• Molecular Weight: 202.256
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30144042
• Nikkaji Number: J99.715C
• Wikipedia: N-Acetyltryptamine
• Wikidata: Q27124335
• Metabolomics Workbench ID: 58878
• ChEMBL ID: CHEMBL33171
• Mol file: 1016-47-3.mol

Synonyms:N-acetyltryptamine;N-acetyltryptamine monohydrochloride

Chemical Property of N-Acetyltryptamine

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 1.51E-09mmHg at 25°C
• Melting Point: 74.0 to 78.0 °C
• Refractive Index: 1.619
• Boiling Point: 484.7 °C at 760 mmHg
• PKA: 16.48±0.46(Predicted)
• Flash Point: 246.9 °C
• PSA: 44.89000
• Density: 1.164 g/cm³
• LogP: 2.23740
• Storage Temp.: 2-8°C
• Solubility.: alcohol: soluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 202.110613074
• Heavy Atom Count: 15
• Complexity: 230

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Acetyltryptamine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: other cyclic peptide (other cyclic peptide)
• Canonical SMILES: CC(=O)NCCC1=CNC2=CC=CC=C21
• Description: The 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. N-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.
• Uses: N-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.

Technology Process of N-Acetyltryptamine

There total 55 articles about N-Acetyltryptamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

tryptamine (61-54-1) + acetic anhydride (108-24-7) → N-Acetyltryptamine (1016-47-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1055/s-0034-1380346

Reference yield: 98.0%

tryptamine (61-54-1) + 3-acetyl-1,3-bis(4-nitrophenyl)triazene → N-Acetyltryptamine (1016-47-3)

Guidance literature:

In acetonitrile; at 20 ℃; for 5h;

DOI:10.1016/S0040-4039(01)01358-2

Reference yield: 95.0%

tryptamine (61-54-1) + acetyl chloride (75-36-5) → N-Acetyltryptamine (1016-47-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.5h;

upstream raw materials:

tryptamine

acetic anhydride

methanol

Nb-acetyl-1-hydroxytryptamine

Downstream raw materials:

N-<2-(2-phenylindol-3-yl)ethyl>acetamide

Refernces

• 1、 Huang,Niemann. "-". . p. 101,105. Retrieved 1952.
• 2、 Singh, Harjit,Sarin, Rakesh. "CARBON TRANSFER REACTIONS OF Δ2-OXAZOLINIUM AND THIAZOLINIUM CATIONS". . p. 1449 - 1460. Retrieved 1986.
• 3、 Maugeri, Zaira,Rother, D?rte. "Application of Imine Reductases (IREDs) in Micro-Aqueous Reaction Systems". . p. 2745 - 2750. Retrieved 2016.
• 4、 Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca. "Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis". . p. 4814 - 4819. Retrieved 2018.
• 5、 Costa, ?ngela C. F.,Cavalcanti, Sócrates C. H.,Santana, Alisson S.,Lima, Ana P. S.,Brito, Thaysnara B.,Oliveira, Rafael R. B.,Macêdo, Nathália A.,Cristaldo, Paulo F.,Araújo, Ana Paula A.,Bacci, Leandro. "Insecticidal activity of indole derivatives against Plutella xylostella and selectivity to four non-target organisms". . p. 973 - 982. Retrieved 2019.
• 6、 Eichberg, Michael J.,Dorta, Rosa L.,Lamottke, Kai,Vollhardt, K. Peter C.. "The formal total synthesis of (±)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition". . p. 2479 - 2481. Retrieved 2000.
• 7、 Nachtigall, Fabiane M.,Santos, Leonardo S.,Sathish, Manda. "Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement". . p. 38672 - 38677. Retrieved 2020.
• 8、 Somei, Masanori,Iwaki, Takako,Yamada, Fumio,Tanaka, Yoshio,Shigenobu, Koki,Koike, Katsuo,Suzuki, Nobuo,Hattori, Atsuhiko. "The ideal synthetic method aimed at the leads for an α2-blocker, an inhibitor of blood platelet aggregation, and an anti-osteoporosis agent". . p. 1565 - 1569. Retrieved 2006.
• 9、 Anderson, Ryan L.,Chen, Yu,Gelis, Ioannis,Leahy, James W.,Lewandowski, Eric M.,Mccaskey, Angelica N.,Merkler, David J.,O'flynn, Brian G.,Prins, Karin Claire,Rios-Guzman, Nasha M.,Shepherd, Britney A.,Suarez, Gabriela. "Characterization of arylalkylamine n-acyltransferase from tribolium castaneum: an investigation into a potential next-generation insecticide target". . p. 513 - 523. Retrieved 2020/03/11.