180989-35-9

Basic information

• Product Name: 1-(3,5-dimethoxyphenyl)-1-heptyne
• Synonyms: 1-(3,5-dimethoxyphenyl)-1-heptyne
• CAS NO: 180989-35-9
• Molecular Weight: 232.323
• Mol File: 180989-35-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(3,5-dimethoxyphenyl)-1-heptyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-dimethoxyphenyl)-1-heptyne(180989-35-9)
• EPA Substance Registry System: 1-(3,5-dimethoxyphenyl)-1-heptyne(180989-35-9)

Safety Data

• Hazardous Substances Data: 180989-35-9(Hazardous Substances Data)

Upstream product

• 110-53-2 1-Bromopentane 
• 171290-52-1 1-Ethynyl-3,5-dimethoxy-benzene 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 500-99-2 3,5-dimethoxyphenol 
• 628-71-7 1-Heptyne 
• 60319-09-7 3,5-dimethoxyphenyl trifluoromethanesulfonate 

Downstream Products

• 180989-30-4 (1R,4R,5R)-4-(4-Hept-1-ynyl-2,6-dihydroxy-phenyl)-6,6-dimethyl-bicyclo[3.1.1]heptan-2-one 
• 180989-36-0 1-(3,5-dihydroxyphenyl)-1-heptyne 

Relevant articles and documents

Development of agonists, partial agonists and antagonists in the Δ8- tetrahydrocannabinol series

Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Δ8-THC analogs with either a rigid acetylenic linkage or a cis- double bond in different positions in the side chain. Various alkyne and cis- ene-Δ8-THC

Pharmacophoric requirements for cannabinoid side chains: Multiple bond and C1'-substituted Δ8-tetrahydrocannabinols

Accumulated evidence indicates that within the cannabinoid structure the aliphatic side chain plays a pivotal role in determining cannabimimetic activity. We describe the synthesis and affinities for the CB1 and CB2 receptors of a series of novel Δ8

Unsaturated side chain β-11-hydroxyhexahydrocannabinol analogs

The cannabinoid side chain is a key pharmacophore in the interaction of cannabinoids with their receptors (CB1 and CB2). To study the stereochemical requirements of the side chain, we synthesized a series of cannabinoids in which rotation around the C1'-C2' bond is blocked. The key steps in the synthesis were the cuprate addition of a substituted resorcinol to (+)- apoverbenone, the TMSOTf-mediated formation of the dihydropyran ring, and the stereospecific introduction of the β-11-hydroxymethyl group. All the analogs tested showed nanomolar affinity for the receptors, the cis-hept-1-ene side chain having the highest affinity for CB1 (K(i) = 0.89 nM) and showing the widest separation between CB1 and CB2 affinities. The parent n-heptyl-β-11- hydroxyhexahydrocannabinol was the least potent binding to CB1 (K(i) = 8.9 nM) and had the lowest selectivity between CB1 and CB2.