1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)-

Base Information

• Chemical Name: 1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)-
• CAS No.: 7795-51-9
• Molecular Formula: C11H14N2
• Molecular Weight: 174.246
• UNII: 5J1FVI77RM
• Nikkaji Number: J1.029.771K
• Wikidata: Q27262352
• ChEMBL ID: CHEMBL2093087
• Mol file: 7795-51-9.mol

Synonyms:Indopan, (S)-;Indopan, (+)-;7795-51-9;1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)-;UNII-5J1FVI77RM;5J1FVI77RM;(2S)-3-(2-Aminopropyl)-1H-indole;S-(+)-alpha-Methyltryptamine;alpha-Methyltryptamine (S)-form [MI];CHEMBL2093087;(+)-indopan;(2S)-1-(1H-indol-3-yl)propan-2-amine;(S)-alpha-Methyltryptamine;SCHEMBL5739268;TQP0678;QSQQQURBVYWZKJ-QMMMGPOBSA-N;CS-M3203;BDBM50227466;PDSP1_000041;PDSP2_000040;S-(+)-.ALPHA.-METHYLTRYPTAMINE;(S)-1-(1H-indol-3-yl)propan-2-amine;(S)-2-(1H-Indol-3-yl)-1-methylethylamine;.ALPHA.-METHYLTRYPTAMINE (S)-FORM [MI];Q27262352;1H-INDOLE-3-ETHANAMINE, .ALPHA.-METHYL-, (.ALPHA.S)-

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Chemical Property of 1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)-

Chemical Property:

• Melting Point: 125-126°
• Boiling Point: 344.5±17.0 °C(Predicted)
• PKA: 17.22±0.30(Predicted)
• PSA: 41.81000
• Density: 1.122±0.06 g/cm3(Predicted)
• LogP: 2.75790
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.115698455
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CNC2=CC=CC=C21)N
• Isomeric SMILES: C[C@@H](CC1=CNC2=CC=CC=C21)N

Technology Process of 1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)-

There total 12 articles about 1H-Indole-3-ethanamine, alpha-methyl-, (alphaS)- 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: 88.0%

1-(1H-indol-3-yl)propan-2-amine (299-26-3,304-54-1) + ethyl 2-methoxyacetate (3938-96-3) → (R)-N-[1-(1H-indol-3-yl)propan-2-yl]-2-methoxyacetamide (1292798-84-5) + (+)-alpha-Methyltryptamine (7795-51-9,304-54-1)

Guidance literature:

With lipase B from Candida antarctica; In tetrahydrofuran; at 30 ℃; for 3.5h; optical yield given as %ee; Inert atmosphere; Enzymatic reaction;

DOI:10.1039/c0ob00800a

Reference yield: 87.0%

(S)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine (113997-60-7) → (+)-alpha-Methyltryptamine (7795-51-9,304-54-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 24h; under 2585.7 Torr;

DOI:10.1021/jm00402a026

Reference yield: 87.0%

(S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane (113997-59-4) → (+)-alpha-Methyltryptamine (7795-51-9,304-54-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 24h; under 2585.7 Torr;

DOI:10.1021/jm00402a026

upstream raw materials:

1-(1H-indol-3-yl)propan-2-amine

2,2,2-trifluoroethylbutyrate

(S)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine

(S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane

Downstream raw materials:

(1R,3S)-5'-chloro-3-methyl-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-indol]-2'(1'H)-one

Refernces

• 1、 Fischereder, Eva-Maria,Pressnitz, Desiree,Kroutil, Wolfgang. "Stereoselective Cascade to C3-Methylated Strictosidine Derivatives Employing Transaminases and Strictosidine Synthases". . p. 23 - 30. Retrieved 2016/01/12.
• 2、 Yeung, Bryan K. S.,Zou, Bin,Rottmann, Matthias,Lakshminarayana, Suresh B.,Ang, Shi Hua,Leong, Seh Yong,Tan, Jocelyn,Wong, Josephine,Keller-Maerki, Sonja,Fischli, Christoph,Goh, Anne,Schmitt, Esther K.,Krastel, Philipp,Francotte, Eric,Kuhen, Kelli,Plouffe, David,Henson, Kerstin,Wagner, Trixie,Winzeler, Elizabeth A.,Petersen, Frank,Brun, Reto,Dartois, Veronique,Diagana, Thierry T.,Keller, Thomas H.. "Spirotetrahydro β-carbolines (spiroindolones): A new class of potent and orally efficacious compounds for the treatment of malaria". experimental part. p. 5155 - 5164. Retrieved 2010/09/05.