1026511-90-9

Basic information

• Product Name: 2-(4-broMo-2,5-diMethoxyphenyl)-N-(2-Methoxybenzyl)ethanaMine
• Synonyms: 2-(4-broMo-2,5-diMethoxyphenyl)-N-(2-Methoxybenzyl)ethanaMine;2-(4-broMo-2,5-diMethoxyphenyl)-N-[(2-Methoxyphenyl)Methyl]ethanaMine;25B-NBOMe HCL;4-Bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]benzeneethanamine;25B-NBOME;BenzeneethanaMine, 4-broMo-2,5-diMethoxy-N-[(2-Methoxyphenyl)Methyl]-
• CAS NO: 1026511-90-9
• Molecular Formula: C₁₈H₂₂BrNO₃
• Molecular Weight: 380.27618
• Mol File: 1026511-90-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 463.293 °C at 760 mmHg
• Flash Point: 233.992 °C
• Appearance: /
• Density: 1.283 g/cm³
• PKA: 8.88±0.20(Predicted)
• CAS DataBase Reference: 2-(4-broMo-2,5-diMethoxyphenyl)-N-(2-Methoxybenzyl)ethanaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-broMo-2,5-diMethoxyphenyl)-N-(2-Methoxybenzyl)ethanaMine(1026511-90-9)
• EPA Substance Registry System: 2-(4-broMo-2,5-diMethoxyphenyl)-N-(2-Methoxybenzyl)ethanaMine(1026511-90-9)

Safety Data

• Hazardous Substances Data: 1026511-90-9(Hazardous Substances Data)

Usage

Uses

4-Bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]benzeneethanamine is a derivative of 2,5-Dimethoxy-4-bromophenethylamine (D469650). 4-Bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]benzeneethanamine is a potent partial agonist for the 5HT2A receptor.

Upstream product

• 93-02-7 2,5-dimethoxybenzaldehyde 
• 108536-18-1 β-dimethoxy-2,5 phenyl nitro ethylene 
• 98537-45-2 4-bromo-2,5-dimethoxy-β-nitrostyrene 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 135-02-4 ortho-anisaldehyde 

Relevant articles and documents

Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes

An expeditious method is reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes.

Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists

N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5- dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2C receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with 1b being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with 1b being more than 400-fold selective for the 5-HT2A receptor.