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115312

Sigma-Aldrich

N-ω-Methyltryptamine

99%

Synonym(s):

2-(Indol-3-yl)-N-methylethanamine, 3-(2-Methylaminoethyl)indole, 3-(2-[Methylamino]ethyl)indole, N-Monomethyltryptamine, Dipterine, N10-Methyltryptamine

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About This Item

Empirical Formula (Hill Notation):
C11H14N2
CAS Number:
61-49-4
Molecular Weight:
174.24
EC Number:
200-507-9
MDL number:
MFCD00005657
UNSPSC Code:
12352100
PubChem Substance ID:
24847209
NACRES:
NA.22

Assay

99%

form

solid

mp

87-89 °C (lit.)

SMILES string

CNCCc1c[nH]c2ccccc12

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

InChI key

NCIKQJBVUNUXLW-UHFFFAOYSA-N

Application

N-ω-Methyltryptamine was used in the preparation of N-acetyl-α−methyltryptamine.
N-ω-methyltryptamine was used in the biosynthesis of dolichantoside using U. tomentosa protein extracts.
Reactant for preparation of:
  • Manzamine analogues for the control of neuroinflammation and cerebral infections
  • Serotonin 4 receptors (5-HT4) receptor agonists
  • A sulful-containing indole alkaloid, glypetelotine
  • Selective inhibitors of cyclin dependent kinase (CDK4)
  • Antagonist of the human tachykinin NK-2 receptor
  • Inhibitors of the tyrosine-specific protein kinase pp60c-src SH2 Domain

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R W Walker et al.
Journal of chromatography, 289, 223-229 (1984-04-27)
A capillary column gas-liquid chromatography selected ion monitoring-based method was developed for the measurement of [13C,15N]N-methyltryptamine ( NMT ) in human urine. The method was employed to establish the extent of conversion of [13C,15N]tryptamine to the correspondingly labeled NMT in
Luigi Servillo et al.
Journal of agricultural and food chemistry, 60(37), 9512-9518 (2012-09-11)
The occurrence of N-methylated tryptamine derivatives in bergamot plant (Citrus bergamia Risso et Poit) is reported for the first time. Interestingly, the most abundant of these substances is N,N,N-trimethyltryptamine, which has not been previously identified in any citrus plant. The
Strictosidine-related enzymes involved in the alkaloid biosynthesis of Uncaria tomentosa root cultures grown under oxidative stress.
Vera-Reyes I, Huerta-Heredia AA, Ponce-Noyola T, et al.
Biotechnology Progress, doi:10-doi:10 (2013)
T J Williams et al.
European journal of pharmacology, 245(3), 197-201 (1993-05-15)
The binding of [3H]5-hydroxytryptamine (5-HT) to rat enteric membranes was inhibited by the inclusion of 5-HT 2-methyl-5-HT, 5-hydroxytryptophan, N,N,N-triethyltryptamine and 2-Br-N,N-diethyltryptamine in the incubation buffer. In contrast, tryptamine, 5-methoxytryptamine and 2-methyl-N,N-diethyltryptamine enhanced binding. Ascorbate and dithiothreitol facilitated and reduced binding
T Takahashi et al.
The International journal of applied radiation and isotopes, 36(12), 965-969 (1985-12-01)
Five indolealkylamines (N,N-dimethyltryptamine, N-methyltryptamine, bufotenine, O-methylbufotenine, N,N,N-trimethyltryptamine iodide) were labeled with 11C by use of 11CH3I. The labeled compounds were synthesized with a radiochemical yield of 2-50% (based on trapped 11CH3I) in 20-35 min with radiochemical purities of more than
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