Structure of Cannabinol. III. Synthesis of Cannabinol, 1-Hydroxy-3-n-amyl-6,6,9-trimethyl-6-dibenzopyran<sup>1</sup>

Adams, Roger; Baker, B. R.; Wearn, R. B.

doi:10.1021/ja01865a083

Cited by 100 publications

(47 citation statements)

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“…The isolation of caimabinol and cannabidiol in the 1940s provided the genera! structure of the active principle of cannabis, but neither of these compoimds had much psychotomimetic activity (Adams et al, 1940a(Adams et al, , 1940b. Mechoulam and his colleagues, in the 1960s, first isolated zl'-tetrahydrocannabinol (^'-THC), which was later found to be primarily responsible for the psychoactive properties of the plant ( Fig.…”

Section: Chemistrymentioning

confidence: 99%

Cannabis: pharmacology and toxicology in animals and humans

Adams¹,

Martin²

1996

Addiction

366

174

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Cannabis is one of the most widely used drugs throughout the world. The psychoactive constituent of cannabis, delta 9-tetrahydrocannabinol (delta 9-THC), produces a myriad of pharmacological effects in animals and humans. For many decades, the mechanism of action of cannabinoids, compounds which are structurally similar to delta 9-THC, was unknown. Tremendous progress has been made recently in characterizing cannabinoid receptors both centrally and peripherally and in studying the role of second messenger systems at the cellular level. Furthermore, an endogenous ligand, anandamide, for the cannabinoid receptor has been identified. Anandamide is a fatty-acid derived compound that possesses pharmacological properties similar to delta 9-THC. The production of complex behavioral events by cannabinoids is probably mediated by specific cannabinoid receptors and interactions with other neurochemical systems. Cannabis also has great therapeutic potential and has been used for centuries for medicinal purposes. However, cannabinoid-derived drugs on the market today lack specificity and produce many unpleasant side effects, thus limiting therapeutic usefulness. The advent of highly potent analogs and a specific antagonist may make possible the development of compounds that lack undesirable side effects. The advancements in the field of cannabinoid pharmacology should facilitate our understanding of the physiological role of endogenous cannabinoids.

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Section: Chemistrymentioning

confidence: 99%

Cannabis: pharmacology and toxicology in animals and humans

Adams¹,

Martin²

1996

Addiction

366

174

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“…Several years later, Todd's group and independently Adam's group elucidated the correct structure of the first natural cannabinoid, CBN. [46][47][48] Subsequently, the second Cannabis constituent, cannabidiol (CBD) was isolated, but its structure was only partially elucidated. 49 Synthetic tetrahydrocannabinol (THC) derivatives were prepared that showed Cannabis-like activity in animal tests.…”

Section: C a N N A B I S S A T I V A ( H E M P ) A N D I T S T Y P mentioning

confidence: 99%

“…249 The ability of dimethylheptyl analogues of 2-AG and noladin ether (46)(47)(48)(49)(50) to activate the CB 1 receptor were not improved by replacement of the terminal pentyl chain with the dimethylheptyl one. 250 To improve enzymatic stability of 2-AG, a-methylated analogues (51a, 51b) of this endocannabinoid were synthesized.…”

Section: B Synthetic Endocannabinoid Analoguesmentioning

confidence: 99%

Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids

Hanŭs

2008

Medicinal Research Reviews

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Research on the chemistry and pharmacology of cannabinoids and endocannabinoids has reached enormous proportions, with approximately 15,000 articles on Cannabis sativa L. and cannabinoids and over 2,000 articles on endocannabinoids. The present review deals with the history of the Cannabis sativa L. plant, its uses, constituent compounds and their biogeneses, and similarity to compounds from Radula spp. In addition, details of the pharmacology of natural cannabinoids, as well as synthetic agonists and antagonists are presented. Finally, details regarding the pioneering isolation of the endocannabinoid anandamide, as well as the pharmacology and potential therapeutic uses of endocannabinoid congeners are presented.

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“…The first successful attempt to identify the first of Cannabis-typical compounds (cannabinoids), cannabinol, was achieved by Wood et al [10] [11]. The correct structure of this compound was solved by Todd and co-workers [13] [14] and independently by Adam et al [15]. The correct structure of this compound was solved by Todd and co-workers [13] [14] and independently by Adam et al [15].…”

Section: Cannabinoids In Plant Andmentioning

confidence: 99%