61367-68-8

Basic information

• Product Name: 4-bromo-3,5-dimethoxyphenylacetonitrile
• Synonyms: 4-bromo-3,5-dimethoxyphenylacetonitrile
• CAS NO: 61367-68-8
• Molecular Weight: 256.099
• Mol File: 61367-68-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-bromo-3,5-dimethoxyphenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-3,5-dimethoxyphenylacetonitrile(61367-68-8)
• EPA Substance Registry System: 4-bromo-3,5-dimethoxyphenylacetonitrile(61367-68-8)

Safety Data

• Hazardous Substances Data: 61367-68-8(Hazardous Substances Data)

Upstream product

• 61367-63-3 4-bromo-3,5-dimethoxybenzyl chloride 
• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 26050-64-6 methyl 4-bromo-3,5-dimethoxybenzoate 
• 61367-62-2 (4-bromo-3,5-dimethoxyphenyl)methanol 

Downstream Products

• 1550060-43-9 4-bromo-3,5-dimethoxyphenyl acetic acid 
• 1550061-20-5 methyl 2-(4-bromo-3,5-dimethoxyphenyl)acetate 
• 1550060-63-3 3-bromo-2,4-dimethoxy-6-(2-methoxy-2-oxoethyl)benzoic acid 
• 1550060-75-7 3-bromo-6-(carboxymethyl)-2,4-dimethoxybenzoic acid (4-bromo-3,5-dimethoxyhomophthalic acid) 
• 1550060-81-5 7-bromo-6,8-dimethoxy-3-(4-methoxyphenethyl)isocoumarin 
• 1550060-88-2 (E)-7-bromo-6,8-dimethoxy-3-(4-methoxystyryl)isocoumarin 
• 1550060-94-0 (E)-7-(3,7-dimethylocta-2,6-dien-1-yl)-6,8-dimethoxy-3-(4-methoxyphenethyl)-1H-isochromen-1-one 
• 1550060-99-5 7-((E)-3,7-dimethylocta-2,6-dien-1-yl)-6,8-dimethoxy-3-((E)-4-methoxystyryl)-1H-isochromen-1-one 
• 130518-14-8 (E)-7-(3,7-dimethylocta-2,6-dien-1-yl)-6,8-dihydroxy-3-(4-hydroxyphenethyl) isocoumarin 
• 130518-15-9 7-((E)-3,7-dimethylocta-2,6-dien-1-yl)-6,8-dihydroxy-3-((E)-4-hydroxystyryl)-1H-isochomen-1-one 

Relevant articles and documents

Chain substituted cannabilactones with selectivity for the CB2 cannabinoid receptor

In earlier work, we reported a novel class of CB2 selective ligands namely cannabilactones. These compounds carry a dimethylheptyl substituent at C3, which is typical for synthetic cannabinoids. In the current study with the focus on the pharmacophoric side chain at C3 we explored the effect of replacing the C1′-gem-dimethyl group with the bulkier cyclopentyl ring, and, we also probed the chain's length and terminal carbon substitution with bromo or cyano groups. One of the analogs synthesized namely 6-[1-(1,9-dihydroxy-6-oxo-6H-benzo[c]chromen-3-yl) cyclopentyl] hexanenitrile (AM4346) has very high affinity (Ki = 4.9 nM) for the mouse CB2 receptor (mCB2) and 131-fold selectivity for that target over the rat CB1 (rCB1). The species difference in the affinities of AM4346 between the mouse (m) and the human (h) CB2 receptors is reduced when compared to our first-generation cannabilactones. In the cyclase assay, our lead compound was found to be a highly potent and efficacious hCB2 receptor agonist (EC50 = 3.7 ± 1.5 nM, E(max) = 89%). We have also extended our structure-activity relationship (SAR) studies to include biphenyl synthetic intermediates that mimic the structure of the phytocannabinoid cannabinodiol.

Lipophilicity and serotonin agonist activity in a series of 4 substituted mescaline analogues

Replacement of the 4 methoxy of mescaline with higher alkyl homologues or with bromine led to increased activity at serotonin receptors in a sheep umbilical artery preparation. This activity appears correlated with lipophilicity, as measured by 1 octanol water partition coefficients, but drops off when the 4 substituent is about five atoms in length. It is suggested that 3,4,5 trisubstitution may give compounds which are as active as those with the 2,4 5 substitution pattern.