7518-21-0

Basic information

• Product Name: 1-METHYLTRYPTAMINE
• Synonyms: 2-(1-METHYL-1H-INDOL-3-YL)ETHANAMINE;2-(1-METHYL-1H-INDOL-3-YL)ETHYLAMINE;1-METHYLTRYPTAMINE;3-(2-AMINOETHYL)-1-METHYLINDOLE;RARECHEM AH BS 0123;1-methyl-1H-indole-3-ethylamine;1-Methyl-1H-indole-3-ethanamine;1-Methyl-3-(2-aminoethyl)-1H-indole
• CAS NO: 7518-21-0
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24
• EINECS: 231-377-1
• Mol File: 7518-21-0.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 330.3 °C at 760 mmHg
• Flash Point: 153.6 °C
• Appearance: /
• Density: 1.09 g/cm³
• BRN: 6874
• CAS DataBase Reference: 1-METHYLTRYPTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLTRYPTAMINE(7518-21-0)
• EPA Substance Registry System: 1-METHYLTRYPTAMINE(7518-21-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 7518-21-0(Hazardous Substances Data)

Usage

General Description

1-Methyltryptamine is a chemical compound classified as a tryptamine derivative, which is structurally related to the neurotransmitter serotonin. It is a psychoactive compound that is known to exhibit hallucinogenic effects in humans. 1-Methyltryptamine acts as a serotonin receptor agonist, binding to and activating the serotonin receptors in the brain, leading to altered perception, mood, and cognitive function. The compound has been studied for its potential therapeutic applications in the treatment of various neurological and neuropsychiatric disorders, as well as for its role in the psychedelic experience. However, the exact mechanism of action and long-term effects of 1-Methyltryptamine are still not fully understood, and further research is needed to determine its safety and efficacy for medical use.

InChI:InChI=1/C11H14N2/c1-13-8-9(6-7-12)10-4-2-3-5-11(10)13/h2-5,8H,6-7,12H2,1H3

Upstream product

• 61-54-1 tryptamine 
• 74-88-4 methyl iodide 
• 104510-16-9 3-(2-amino-ethyl)-1-methyl-indole-2-carboxylic acid 
• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 122-39-4 diphenylamine 
• 2731-00-2 1-methyl-3-[(E)-2-nitrovinyl]-1H-indole 
• 373-68-2 tetramethylammonium fluoride 
• 120-72-9 indole 
• 110-88-3 1,3,5-Trioxan 
• 2731-00-2 N_a-methyl-nitroethyleneindole 
• 5956-86-5 tryptamine-2-carboxylic acid 
• 71672-19-0 9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one 

Downstream Products

• 56999-36-1 N-benzyl-1-methyltryptamine 
• 75671-06-6 6-methyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino<4,5-b>indole 
• 75671-04-4 N-(2-hydroxy-2-phenylethyl)-1-methyltryptamine hydrochloride 
• 75671-05-5 2-{Benzyl-[2-(1-methyl-1H-indol-3-yl)-ethyl]-amino}-1-phenyl-ethanol; hydrochloride 
• 75671-12-4 3,6-dimethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino<4,5-b>indole 
• 881204-49-5 C₁₇H₁₇N₃O₂ 
• 1516902-70-7 5-(4-bromobenzyloxy)-4-oxo-4H-chromene-2-carboxylic acid [2-(1-methyl-1H-indol-3-yl)ethyl]amide 
• 1318072-81-9 4-methyl-N-(2-(1-methyl-1H-indol-3-yl)ethyl)benzenesulfonamide 

Relevant articles and documents

Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines

The development of new one-pot sequential cyclizations involving a Vilsmeier-Haack reaction followed by an organocatalyzed Mannich reaction is reported. This synthetic strategy gives access to functionalized indolizidines and quinolizidines in one operation from readily synthesized precursors. Yields and diastereoselectivities are good to excellent when formamides are used to trigger the key step, bearing either an electron-rich aryl or a pyrrole as the nucleophilic partner in the first cyclization.

Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride

We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.

Tryptamine Synthesis by Iron Porphyrin Catalyzed C?H Functionalization of Indoles with Diazoacetonitrile

The functionalization of C?H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C?H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.