2-Methyltryptamine

Base Information

• Chemical Name: 2-Methyltryptamine
• CAS No.: 2731-06-8
• Molecular Formula: C11H14N2
• Molecular Weight: 174.246
• Hs Code.: 2933990090
• European Community (EC) Number: 220-347-3
• DSSTox Substance ID: DTXSID30181755
• Nikkaji Number: J46.767G
• Wikidata: Q63392397
• ChEMBL ID: CHEMBL2358910
• Mol file: 2731-06-8.mol

Synonyms:2731-06-8;2-Methyltryptamine;2-(2-methyl-1H-indol-3-yl)ethanamine;2-methylindole-3-ethylamine;2-(2-Methyl-1H-indol-3-yl)-ethylamine;1H-Indole-3-ethanamine, 2-methyl-;3-(2-Aminoethyl)-2-methylindole;2-(2-methyl-1H-indol-3-yl)ethan-1-amine;2-methyl tryptamine;MFCD00130185;1h-indole-2-methyl-3-ethanamine;2-Methyl-1H-indole-3-ethylamine;2-METHYL-1H-INDOLE-3-ETHANAMINE;2-Methyltryptamin;F66;Cambridge id 5112300;TimTec1_002997;Oprea1_321802;Oprea1_726612;MLS000122004;SCHEMBL1424220;CHEMBL2358910;DTXSID30181755;ART-CHEM-BB B006949;HMS1542I05;HMS2388D13;BCP25815;EINECS 220-347-3;FD7377;STK072030;AKOS000308360;AB03694;AM84864;DS-3051;FS-1950;NCGC00245043-01;SMR000119444;SY027668;2-(2-methyl-1H-indol-3-yl)-1-ethanamine;BB 0216355;CS-0008756;EU-0053050;FT-0648066;M2055;EN300-65968;A923879;W-204216;BRD-K57059123-001-01-3;Q63392397;Z336079656

Chemical Property of 2-Methyltryptamine

Chemical Property:

• Appearance/Colour: Brown solid
• Vapor Pressure: 3.69E-05mmHg at 25°C
• Melting Point: 106.0 to 110.0 °C
• Refractive Index: 1.65
• Boiling Point: 353 °C at 760 mmHg
• PKA: 17.78±0.30(Predicted)
• Flash Point: 194.4 °C
• PSA: 41.81000
• Density: 1.126 g/cm³
• LogP: 2.67780
• Storage Temp.: 0-10°C
• XLogP3: 1.8
• 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:

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

2-Methyltryptamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N1)CCN
• Uses: Key starting material in the synthesis of the histone deacetylase inhibitor LBH589.

Technology Process of 2-Methyltryptamine

There total 27 articles about 2-Methyltryptamine 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: 89.0%

5-chloro-pentanal (20074-80-0) + phenylhydrazine (100-63-0) → 2-methyltryptamine (2731-06-8)

Guidance literature:

In ethanol; at 80 ℃; for 18h;

DOI:10.1016/j.chembiol.2021.04.004

Reference yield: 82.0%

5-chloro-2-pentanone (5891-21-4) + phenylhydrazine (100-63-0) → 2-methyltryptamine (2731-06-8)

Guidance literature:

In ethanol; at 80 ℃; for 4h;

DOI:10.1021/ol501409a

Reference yield: 78.0%

N-[2-(2-methyl-1H-indol-3-yl)ethyl]acetamide (39760-01-5) → 2-methyltryptamine (2731-06-8)

Guidance literature:

With ammonium bromide; ethylenediamine; at 100 ℃; for 7h; Microwave irradiation;

DOI:10.1021/acs.joc.5b00195

upstream raw materials:

2-(2-methyl-1H-indol-3-yl)acetonitrile

2-Methyl-3-(2-nitroethyl)-1H-indole

indole

N-Acetyltryptamine

Downstream raw materials:

(E)-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylic acid methyl ester

(E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride

3-chloro-2-fluoro-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide

2-fluoro-4-hydroxy-N-(2-(2-methyl-1H-indol-3-yl)ethyl)benzamide

Refernces

• 1、 Chen, Shanwen,Zhang, Peiming,Chen, Huali,Zhang, Pu,Yu, Yu,Gan, Zongjie. "An improved and efficient synthesis of panobinostat". . p. 471 - 473. Retrieved 2018.
• 2、 Li, Xiaoyang,Jiang, Yuqi,Peterson, Yuri K.,Xu, Tongqiang,Himes, Richard A.,Luo, Xin,Yin, Guilin,Inks, Elizabeth S.,Dolloff, Nathan,Halene, Stephanie,Chan, Sherine S. L.,Chou, C. James. "Design of Hydrazide-Bearing HDACIs Based on Panobinostat and Their p53 and FLT3-ITD Dependency in Antileukemia Activity". . p. 5501 - 5525. Retrieved 2020/06/10.
• 3、 Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel. "5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations". supporting information. p. 9496 - 9500. Retrieved 2019/06/27.