A Procedure for the Conversion of Cannabidiol into 12β-Substituted Tetrahydrocannabinols (THC's): Synthesis of 12β-Hydroxy-Δ<sup>β</sup>THC<sup>1</sup>

Jorapur, Vaman S.; Duffley, R. P.; Razdan, Raj K.

doi:10.1080/00397918408063751

Cited by 13 publications

(6 citation statements)

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“…Further SAR studies in our laboratory showed [53] that high activity and potency was retained in the (equatorial) 12b-hydroxy-Á 8 -THC. With this background Tius and Makriyannis' groups [12,54,55] developed hybrid cannabinoids, which incorporate the structural features of Á 9 -THC and the nonclassical cannabinoid CP 55,940.…”

Section: Modifications At C-6 Positionmentioning

confidence: 96%

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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Section: Modifications At C-6 Positionmentioning

confidence: 96%

Structure–Activity Relationships of Classical Cannabinoids

Razdan

2009

The Cannabinoid Receptors

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“…Analytical characterizations of and synthetic methodologies for all five metabolites hydroxylated at the pentyl side chain were described in the early 1970s. 57 , 57a , 106 , 107 The syntheses of the epimeric 6α- and 6β-OH-CBD 108 as well as the syntheses of the 7-OH-CBD 74 , 108–110 and the nonhuman metabolite species 10-OH-CBD 109 , 111 have been reported. The rabbit metabolite 8,9-diOH-CBD was obtained by incubating 8,9-epoxy-CBD 112 with guinea pig hepatic microsomes.…”

Section: Synthesis Of Cbd Metabolitesmentioning

confidence: 99%

Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy

Ujváry¹,

Hanŭs

2016

Cannabis and Cannabinoid Research

230

204

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Cannabidiol (CBD), the main nonpsychoactive constituent of Cannabis sativa, has shown a wide range of therapeutically promising pharmacological effects either as a sole drug or in combination with other drugs in adjunctive therapy. However, the targets involved in the therapeutic effects of CBD appear to be elusive. Furthermore, scarce information is available on the biological activity of its human metabolites which, when formed in pharmacologically relevant concentration, might contribute to or even account for the observed therapeutic effects. The present overview summarizes our current knowledge on the pharmacokinetics and metabolic fate of CBD in humans, reviews studies on the biological activity of CBD metabolites either in vitro or in vivo, and discusses relevant drug–drug interactions. To facilitate further research in the area, the reported syntheses of CBD metabolites are also catalogued.

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“…6 Despite the wide variety of substituents in different pharmacophores on the classical THC structure, halogen substitution has received little attention. A small number of halogenated cannabinoids have been synthesized including 10-bromo-cannabidiol diacetate, 7 3-bromo-tetrahydrocannabiorcol, 8 11-bromo-∆ 8 -THC acetate, 9 and a few fluoro-, bromo-, and iodo-substituted cannabinoids. [10][11][12][13][14][15] With the exception of iodinated derivatives, which were developed for radioimmunological assays, these halogenated analogs were obtained as synthetic intermediates and did not undergo biological testing.…”

Section: Introductionmentioning

confidence: 99%

The role of halogen substitution in classical cannabinoids: A CB1 pharmacophore model

Nikas

Grzybowska

Papahatjis

et al. 2004

AAPS J

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The presence of halogens within the classical cannabinoid structure leads to large variations in the compounds' potencies and affinities for the CB1 receptors. To explore the structure activity relationships within this class of analogs we have used a series of halogen-substituted (-)-∆ 8 -tetrahydrocannabinol analogs and compared their affinities for the CB1 cannabinoid receptor. Our results indicate that halogen substitution at the end-carbon of the side chain leads to an enhancement in affinity with the bulkier halogens (Br, I) producing the largest effects. Conversely, 2-iodo substitution on the phenolic ring leads to a 2-fold reduction in affinity while iodo-substitution in the C1'-position of the side chain lowers the compound's affinity for CB1 by more than 8-fold. The pharmacophoric requirements resulting from halogen-substitution are explored using computer modeling methods.

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A Procedure for the Conversion of Cannabidiol into 12β-Substituted Tetrahydrocannabinols (THC's): Synthesis of 12β-Hydroxy-Δ^βTHC¹

Cited by 13 publications

References 4 publications

Structure–Activity Relationships of Classical Cannabinoids

Structure–Activity Relationships of Classical Cannabinoids

Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy

The role of halogen substitution in classical cannabinoids: A CB1 pharmacophore model

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A Procedure for the Conversion of Cannabidiol into 12β-Substituted Tetrahydrocannabinols (THC's): Synthesis of 12β-Hydroxy-ΔβTHC1

Cited by 13 publications

References 4 publications

Structure–Activity Relationships of Classical Cannabinoids

Structure–Activity Relationships of Classical Cannabinoids

Human Metabolites of Cannabidiol: A Review on Their Formation, Biological Activity, and Relevance in Therapy

The role of halogen substitution in classical cannabinoids: A CB1 pharmacophore model

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Product

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A Procedure for the Conversion of Cannabidiol into 12β-Substituted Tetrahydrocannabinols (THC's): Synthesis of 12β-Hydroxy-Δ^βTHC¹