96624-18-9

Usage

Class

Organic compounds

Subclass

Tryptamines

Structure

A derivative of tryptamine with a bromine atom attached to the indole ring

Potential applications

Medicinal chemistry, specifically in the development of pharmaceuticals targeting the serotonin receptor system

Psychoactive effects

Known to have psychoactive effects

Natural sources

Found in plants and fungi

Research status

The specific properties and potential uses are a subject of ongoing research and exploration in the fields of pharmacology and neuroscience.

InChI:InChI=1/C10H11BrN2/c11-8-1-2-9-7(3-4-12)6-13-10(9)5-8/h1-2,5-6,13H,3-4,12H2

Upstream product

• 52415-29-9 6-bromo-1H-indole 
• 120-72-9 indole 
• 78508-22-2 β-dimethylamino-2-nitrostyrene 
• 319493-07-7 3-(2-nitrovinyl)-6-bromo-1H-indole 
• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 
• 496-15-1 1-indoline 
• 60956-26-5 4-bromo-2-nitrotoluene 
• 119-32-4 4-Methyl-3-nitroanilin 
• 5548-10-7 indole-3-glyoxylamide 

Downstream Products

• 1631136-29-2 C₂₈H₂₉BrN₂O 
• 1007893-80-2 (7-bromo-9H-pyrido[3,4-b]indol-1-yl)(3,5-dibromo-4-hydroxyphenyl)methanone 
• 1400791-74-3 N-(2-(5-bromo-1H-indol-3-yl)ethyl)-1-phenylprop-2-en-1-amine 
• 1384331-19-4 C₃₆H₃₄BrN₃O₂ 
• 1384331-21-8 C₃₇H₃₆BrN₃O₃ 
• 1384331-18-3 C₃₅H₃₂BrN₃O₂ 
• 1384331-16-1 C₃₅H₃₀BrN₃O₂ 
• 108061-47-8 7-bromo-1,2,3,4-tetrahydro-β-carboline 
• 1015233-64-3 C₂₅H₂₀BrN₃O₃S 

Relevant academic research and scientific papers

Concerning the preparation of 6-bromotryptamine

Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.

Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C

A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.