Tryptamine

Base Information

• Chemical Name: Tryptamine
• CAS No.: 61-54-1
• Molecular Formula: C10H12N2
• Molecular Weight: 160.219
• Hs Code.: 29339990
• European Community (EC) Number: 200-510-5
• UNII: 422ZU9N5TV
• DSSTox Substance ID: DTXSID2075340
• Nikkaji Number: J4.816J
• Wikipedia: Tryptamine
• Wikidata: Q409439
• Pharos Ligand ID: LTQ7FA4H1WYU
• Metabolomics Workbench ID: 37195
• ChEMBL ID: CHEMBL6640
• Mol file: 61-54-1.mol

Synonyms:3-(2-aminoethyl)indole;tryptamine;tryptamine monohydrochloride;tryptamine sulfate

Chemical Property of Tryptamine

Chemical Property:

• Appearance/Colour: White to orange crystalline powder
• Vapor Pressure: 6.14E-06mmHg at 25°C
• Melting Point: 113-116 °C(lit.)
• Refractive Index: 1.668
• Boiling Point: 378.766 °C at 760 mmHg
• PKA: 10.2(at 25℃)
• Flash Point: 187.672 °C
• PSA: 41.81000
• Density: 1.158 g/cm³
• LogP: 2.36940
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: water: soluble1g/L at 20°C
• Water Solubility.: negligible
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 160.100048391
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

≥99% ^*data from raw suppliers

Tryptamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-41-37/38-22
• Safety Statements: 24/25-36/37/39-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCN
• Description: Tryptamine is a monoamine alkaloid that can be synthesized by decarboxylation of the amino acid tryptophan. Notably, tryptamine can be found in fungi, plants, Amphibia, animals, and microbes. Tryptamine has an indole ring structure and a fused double ring that is composed of a benzene ring and a pyrrole ring, linked to an amino group by 2-carbon side chain. The indole ring is the vital nucleus of many complex natural products that have significance in drug discovery as well as some synthetic and non-synthetic drugs that are based on tryptamine skeleton. The chemical’s distinct structure is an approximation to the neurotransmitter serotonin as well-known drugs and hallucinogens. Tryptamine’s significance as psychedelic drugs, neuromodulator, and neurotransmitter is well understood due to its presence in mammalian brain in small amounts. Tryptamine is an indole alkaloid and intermediate in the biosynthesis of serotonin and the phytohormone melatonin in plants. It increases the levels of the terpenoid indole alkaloids ajmalicine, strictosidine, and catharanthine in cultures of C. roseus. Tryptamine is also a product of tryptophan metabolism in mammals. Tryptamine derivatives have been synthetically produced as hallucinogenic drugs of abuse that act on the serotonergic system.
• Uses: Tryptamine is a monoamine alkaloid found in plants. Tryptamine is commonly used in the preparation of biologically active compounds such as neurotransmitters and psychedelics.

Technology Process of Tryptamine

There total 115 articles about Tryptamine 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%

3-(2-nitroethyl)indole (31731-23-4) → tryptamine (61-54-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 24h; under 760.051 Torr;

DOI:10.3390/md11051427

Reference yield: 98.0%

tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate (1042701-07-4) → tryptamine (61-54-1)

Guidance literature:

tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 0 - 25 ℃; Inert atmosphere;

With sodium hydrogencarbonate; In water; pH=> 7; Inert atmosphere; Saturated solution;

DOI:10.1002/anie.200800404

Reference yield: 98.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → tryptamine (61-54-1)

Guidance literature:

With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase; In various solvent(s); at 30 ℃; for 48h;

upstream raw materials:

indole-3-acetonitrile

3-(2-bromoethyl)-1H-indole

3-indolylacetamide

3-[(E)-2-nitroeth-1-enyl]-1H-indole

Downstream raw materials:

15,16,17,18,19,20-hexahydroyohimban-21-one

9H-benzo[c]indolo[3,2,1-ij][1,5]naphthyridin-9-one

N-phthalimidotryptamine

(+/-)-3a-methyl-(3ar,8ac)-1,2,3,4a,8,8a-hexahydro-pyrrolo[2,3-b]indole

Refernces

• 1、 Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta. "N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential". . . Retrieved 2021/08/17.
• 2、 Son, Jung-Ho,Phuan, Puay-Wah,Zhu, Jie S.,Lipman, Elena,Cheung, Amy,Tsui, Ka Yi,Tantillo, Dean J.,Verkman, Alan S.,Haggie, Peter M.,Kurth, Mark J.. "1-BENZYLSPIRO[PIPERIDINE-4,1′-PYRIDO[3,4-b]indole] ‘co-potentiators’ for minimal function CFTR mutants". . . Retrieved 2020/10/26.