2009-03-2

Usage

Uses

Used in Pharmaceutical Industry:
N-Methyl-5-methoxy-1H-indole-3-ethanamine is used as a pharmaceutical agent for its agonistic effect on the serotonin 5-HT2A receptor. This property makes it a potential candidate for the development of drugs targeting various neurological and psychiatric disorders, as the 5-HT2A receptor plays a significant role in modulating mood, cognition, and perception.

InChI:InChI=1/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3

Upstream product

• 2426-27-9 2-(5-methoxy-indol-3-yl)-N-methyl-2-oxo-acetamide 
• 96096-65-0 N-[2-(5-methoxy-1H-indol-3-yl)ethyl]benzyloxycarboxamide 
• 61-54-1 tryptamine 
• 66-83-1 5-methoxytryptamine hydrochloride 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 79-22-1 methyl chloroformate 
• 104510-12-5 N-(2-(5-methoxy-1H-indol-3-yl)ethyl)formamide 
• 102016-76-2 N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide 
• 68935-49-9 5-methoxy-3-(2-nitroethyl)-1H-indole 
• 1006-94-6 5-methoxylindole 
• 205384-46-9 1-hydroxy-N-methoxycarbonyl-N-methyltryptamine 
• 205384-45-8 2,3-dihydro-N-methoxycarbonyl-N-methyltryptamine 
• 63637-70-7 methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate 
• 58635-45-3 methyl 2-(1-H-indol-3-yl)ethylcarbamate 

Downstream Products

• 96096-55-8 5-methoxy-N-methyl-N-isopropyltryptamine 
• 1516902-87-6 5-(4-bromobenzyloxy)-2-({[2-(5-methoxy-1H-indole-3-yl)ethyl]methylamino}methyl)-chromen-4-one 
• 1516902-73-0 5-(4-bromobenzyloxy)-4-oxo-4H-chromene-2-carboxylic acid [2-(5-methoxy-1H-indol-3-yl)ethyl]methylamide 

Relevant academic research and scientific papers

Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines

The pyrroloindoline core is found in many natural products. These structures often differ at the C3a position, which may be substituted with an oxygen, nitrogen, or sp3- or sp2-hybridized carbon. Utilizing a trichloroacetimidate leaving group, a diversity-oriented approach to these structures has been developed. The trichloroacetimidate intermediate allows for the rapid incorporation of anilines, alcohols, thiols, and carbon nucleophiles. This method was applied in the synthesis of arundinine and a formal synthesis of psychotriasine.

Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide

Oxidative rearrangement of indoles is an important transformation to yield 2-oxindoles and spirooxindoles, which are present in many pharmaceutical agents and bioactive natural products. Previous oxidation methods show either broad applicability or greenness but rarely achieve both. Reported is the discovery of Fenton chemistry-enabled green catalytic oxidative rearrangement of indoles, which has wide substrate scope (42 examples) and greenness (water as the only stoichiometric byproduct) at the same time. Detailed mechanistic studies revealed that the Fenton chemistry generated hydroxyl radicals that further oxidize bromide to reactive brominating species (RBS: bromine or hypobromous acid). Thisin situgenerated RBS is the real catalyst for the oxidative rearrangement. Importantly, the RBS is generated under neutral conditions, which addresses a long-lasting problem of many haloperoxidase mimics that require a strong acid for the oxidation of bromide with hydrogen peroxide. It is expected that this new catalytic Fenton-halide system will find wide applications in organic synthesis.

Aromatic heterocyclic derivative and application thereof in medicine

The invention provides aromatic heterocyclic derivatives or stereoisomers, tautomers, nitrogen oxides, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, which are used for treating Alzheimer's disease. The invention also discloses pharmaceutical compositions containing the compounds and a method for treating Alzheimer's disease by using the compounds or the pharmaceutical compositions provided by the invention.

Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones

The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.

MELATONIN DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL DYSFUNCTIONS

The present invention relates to compounds of the general formula (1): wherein R1, R2, R3, R4 and R5 are H or a moiety of the formula : -(R6)n-R7; with R6 is a is an alkyl chain and R7 is, a moiety selected in the group consisting of -Cn,H2n2,+I, a cycloalkyl moiety, -N(Cn,H2n,+I)(Cn,H2n,+1), -NH-cycloalkyl, -O(Cn,H2n'+I), -0-cycloalkyl, =O, =S, -NO2, -I, -Br, -Cl, -F, -CF3, -OCF3, -COOH, -S03H, -P03H2, -CN, A3 and A4 are, C, N,O or S;m is from 0 to 2; and to their use for the treatment and/or prevention of diseases and conditions mediated by the imbalance of acetylcholine, and for treating and/or preventing glutamate excitotoxicity.

The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry

Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.

The chemistry of indoles. CVII. A synthesis of 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles and a new finding on pictet-spengler reaction

Serotonins were found to produce 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles by simple heating with amines under an oxygen atmosphere. Serotonins also reacted with various aldehydes to provide 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]

Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine

Simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), and melatonin (2), and the first total synthesis of N-(indol-3-yl)methyl-N-methyl-5-methoxytryptamine (3) from tryptamine (4a) are reported through acid catalyzed nucleophilic substitution reaction of 1-hydroxytryptamines.

Psychotomimetic N-Methyl-N-isopropyltryptamines. Effects of Variation of Aromatic Oxygen Substituents

Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man.In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues.Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile.The 5-methoxy congeger 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena.Other members of the series exhibited diminished effects.