[2-(1H-indol-3-yl)ethyl](methyl)amine

• ChemBase ID: 147193
• Molecular Formular: C11H14N2
• Molecular Mass: 174.24226
• Monoisotopic Mass: 174.11569846
• SMILES: CNCCc1c[nH]c2c1cccc2
• Canonical SMILES: CNCCc1c[nH]c2c1cccc2
• InChI: InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
• InChIKey: NCIKQJBVUNUXLW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(1H-indol-3-yl)ethyl](methyl)amine
• IUPAC Traditional name: methyltryptamine
• Synonyms: 2-(Indol-3-yl)-N-methylethanamine; N-Monomethyltryptamine; Dipterine; N10-Methyltryptamine; 3-(2-Methylaminoethyl)indole; 3-(2-[Methylamino]ethyl)indole; N-ω-Methyltryptamine; Nω-Methyltryptamine Hydrochloride; [2-(1H-Indol-3-yl)ethyl]methylamine Hydrochloride; N-Methyltryptamine Hydrochloride; 2-(1H-Indol-3-yl)-N-methylethanamine Hydrochloride; 3-(2-Methylaminoethyl)indole Hydrochloride; Dipterine Hydrochloride; N-Methyl-1H-indole-3-ethanamine Hydrochloride; N-Monomethyltryptamine Hydrochloride; N10-Methyltryptamine Hydrochloride; Nb-Methyltryptamine Hydrochloride; 3-(2-[甲氨基]乙基)吲哚; 3-(2-甲基氨基乙基)吲哚; N-ω-甲基色胺

Database IDs

• CAS Number: 942-27-8; 61-49-4
• EC Number: 200-507-9
• MDL Number: MFCD00005657
• PubChem SID: 24847209; 162241384
• PubChem CID: 6088

CALCULATED PROPERTIES

• Acid pKa: 17.167824
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -1.3114282
• LogD (pH = 7.4): -0.82565516
• Log P: 1.9190178
• Molar Refractivity: 55.1475 cm^3
• Polarizability: 22.619232 Å^3
• Polar Surface Area: 27.82 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Light Brown to Brown Solid
• Melting Point: >155°C (dec.); 87-89 °C(lit.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C11H14N2

DETAILS

Sigma Aldrich - 115312

Packaging
1 g in glass bottle
100 mg in glass bottle
Application
Reactant for preparation of:
• Manzamine analogues for the control of neuroinflammation and cerebral infections1
• Serotonin 4 receptors (5-HT4) receptor agonists2
• A sulful-containing indole alkaloid, glypetelotine3
• Selective inhibitors of cyclin dependent kinase (CDK4)4
• Antagonist of the human tachykinin NK-2 receptor5
• Inhibitors of the tyrosine-specific protein kinase pp60c-src SH2 Domain6
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 115312.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M331920

N-Methyltryptamine is a N-monomethylated derivative of tryptamine. N-Methyltryptamine, unlike its unmethylated counterpart, does not produce any psychoactive effects. High levels of N-Methyltryptamine have been found in cisternal cerebrospinal fluid of pa

REFERENCES

• Schmid, C. et al.: J. Neurosci., 30, 13513 (2010)
• Uebelhack, R. et al.: Biomed. Biochim. Acta, 42, 1343 (2010)