22663-41-8

Basic information

• Product Name: (6aR)-3-(1,1-Dimethylpentyl)-6aβ,7,10,10aα-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
• Synonyms: (-)-1',1'-Dimethyl-Δ8-tetrahydrocannabinol;(6aR)-3-(1,1-Dimethylpentyl)-6aβ,7,10,10aα-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
• CAS NO: 22663-41-8
• Molecular Formula: C23H34O2
• Molecular Weight: 342.51486
• Mol File: 22663-41-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6aR)-3-(1,1-Dimethylpentyl)-6aβ,7,10,10aα-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (6aR)-3-(1,1-Dimethylpentyl)-6aβ,7,10,10aα-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol(22663-41-8)
• EPA Substance Registry System: (6aR)-3-(1,1-Dimethylpentyl)-6aβ,7,10,10aα-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol(22663-41-8)

Safety Data

• Hazardous Substances Data: 22663-41-8(Hazardous Substances Data)

Upstream product

• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 22930-09-2 2-(3,5-dihydroxyphenyl)-2-methylhexane 
• 861892-40-2 (4R)-1-methyl-4-(2-(1-propylene))-2-cyclohexene-2-ol 
• 22972-63-0 α,α-dimethyl-3,5-dimethoxyphenylacetonitrile 
• 120078-30-0 2-(3,5-dimethoxyphenyl)-2-methylpropanal 
• 22930-08-1 1,3-dimethoxy-5-(2-methylhexan-2-yl)benzene 

Downstream Products

• 105823-04-9 JWH 057 

Relevant articles and documents

1-Bromo-3-(1′,1′-dimethylalkyl)-1-deoxy-Δ8- tetrahydrocannabinols: New selective ligands for the cannabinoid CB2 receptor

Δ8-Tetrahydrocannabinol (26), 3-(1′,1′- dimethylbutyl)- (12), 3-(1′,1′-dimethylpentyl)- (13), 3-(1′,1′-dimethylhexyl)- (14) and 3-(1′,1′- dimethylheptyl)-Δ8-tetrahydrocannabinol (15) have been converted into the corresponding 1-bromo-1-deoxy-Δ8- tetrahydrocannabinols (25, 8-11). This was accomplished using a protocol developed in our laboratory in which the trifluoromethanesulfonate of a phenol undergoes palladium mediated coupling with pinacolborane. Reaction of this dioxaborolane with aqueous-methanolic copper(II) bromide provides the aryl bromide. The affinities of these bromo cannabinoids for the cannabinoid CB 1 and CB2 receptors were determined. All of these compounds showed selectivity for the CB2 receptor and one of them, 1-bromo-1-deoxy-3-(1′,1′-dimethylhexyl)-Δ8- tetrahydrocannabinol (10), exhibits 52-fold selectivity for this receptor with good (28 nM) affinity.

Structure-activity relationships for 1′,1′-dimethylalkyl-Δ8-tetrahydrocannabinols

A series of 1′,1′-dimethylalkyl-Δ8-tetrahydrocannabinol analogues with C-3 side chains of 2-12 carbon atoms has been synthesized and their in vitro and in vivo pharmacology has been evaluated. The lowest member of the series, 1′,1′-dimethylethyl-Δ8-THC (8, n=0) has good affinity for the CB1 receptor, but is inactive in vivo. The dimethylpropyl (8, n=1) through dimethyldecyl (8, n=8) all have high affinity for the CB1 receptor and are full agonists in vivo. 1′,1′-Dimethylundecyl-Δ8-THC (8, n=9) has significant affinity for the receptor (Ki=25.8±5.8 nM), but has reduced potency in vivo. The dodecyl analogue (8, n=10) has little affinity for the CB1 receptor and is inactive in vivo. A quantitative structure-activity relationship study of the side chain region of these compounds is consistent with the concept that for optimum affinity and potency the side chain must be of a length which will permit its terminus to loop back in proximity to the phenolic ring of the cannabinoid.