9-Nor-9-hydroxyhexahydrocannabinols. Synthesis, some behavioral and analgesic properties, and comparison with the tetrahydrocannabinols

Wilson, Raymond S.; May, Everette L.; Martin, Billy R.; Dewey, William L.

doi:10.1021/jm00231a017

Cited by 61 publications

(36 citation statements)

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“…Little attention has been paid to the pharmacological effects of HHCs, although some HHC derivatives were reported to have THC-like pharmacological effects [15][16][17]. In the present study, pharmacological effects of 9α-OH-HHC and 8-OH-iso-HHC have been assessed in mice by catalepsy, hypothermia, pentobarbital-induced sleep prolongation, and antinociception as indices, and have been compared with those of CBD or ∆ 9 -THC.…”

Section: Resultsmentioning

confidence: 99%

Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice

et al. 2007

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sleeping time by 1.8 to 8.0 times as compared with the control solution with 1% Tween 80-saline. The ED 50 values (mg/kg, i.v.) of 9α-OH-HHC and 8-OH-iso-HHC for the antinociceptive effect were 14.1 and 39.4, respectively. The present study demonstrated that CBD can be converted to ∆ 9 -THC and its related cannabinoids, 9α-OH-HHC and 8-OH-iso-HHC, in artifi cial gastric juice, and that these HHCs show ∆ 9 -THC-like effects in mice, although their pharmacological effects were less potent than those of ∆ 9 -THC.

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Section: Resultsmentioning

confidence: 99%

Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice

et al. 2007

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“…Since cannabinoids are generally very lipid-soluble, solubilizing agents for pharmacological studies are used, but these agents, which have pharmacological effects of their own, can be avoided by making available cannabinoids which are water-soluble. By the formation of various esters of phenols, which hydrolyze at different rates, a series of water-soluble cannabinoids [37,38] SAR studies [41][42][43] show that the presence of a hydroxyl group at C-11 is not a prerequisite for activity since the 9-nor compound retains activity. However, the metabolite of Á 9 -/Á 8 -THC, (i.e., 11-hydroxymethyl-THC) is approximately three times more active than the parent compound.…”

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confidence: 99%

Structure–Activity Relationships of Classical Cannabinoids

Razdan

2009

The Cannabinoid Receptors

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In this chapter an overview of the more recent developments in the structure-activity relationships (SARs) of classical cannabinoids is discussed, especially the profound pharmacological effects produced by various chemical entities in the side chain at C-3, the hydroxyl at C-1, C-11, and hydroxyalkyl chains at C-6. Also cardiovascular studies point to the presence of a novel cannabinoid subtype receptor and the antagonist activity of cannabidiol has opened up new areas for research. Ligands, which had either a unique pharmacological profile, were potent agonists, partial agonists/antagonists, or were CB2 selective, were identified, generating leads with the potential to be drugs in the treatment of various diseases.

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“…At the time, i.e., during the mid-to late 1970s, it was hoped that it would be possible to separate the analgesic from other cannabinoid induced effects. A study by Wilson et al (1976) had suggested the potential for such a separation. However, this did not materialize and eventually Pfizer retreated from this early cannabinoid medication research program.…”

Section: “Spice” Compounds and Discriminationmentioning

confidence: 99%

“Herbal incense”: Designer drug blends as cannabimimetics and their assessment by drug discrimination and other in vivo bioassays

Järbe

Gifford

2014

Life Sciences

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Recently, synthetic cannabinoids originally designed for testing in the laboratory only have found use recreationally in designer herbal blends, originally called “Spice”. The myriad of compounds found are for the most part potent full agonists of the cannabinoid receptor 1, producing effects similar to tetrahydrocannabinol (THC) and marijuana. Drug discrimination of these compounds offers a specific behavioral test that can help determine whether these new synthetic compounds share a similar “subjective high”with the effects of marijuana/THC. By utilization of drug discrimination and other behavioral techniques, a better understanding of these new “designer” cannabinoids may be reached to assist in treating both the acute and chronic effects of these drugs. The paper provides a brief exposé of modern cannabinoid research as a backdrop to the recreational use of designer herbal blend cannabimimetics.

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9-Nor-9-hydroxyhexahydrocannabinols. Synthesis, some behavioral and analgesic properties, and comparison with the tetrahydrocannabinols

Cited by 61 publications

References 0 publications

Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice

Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice

Structure–Activity Relationships of Classical Cannabinoids

“Herbal incense”: Designer drug blends as cannabimimetics and their assessment by drug discrimination and other in vivo bioassays

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