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Record W2253818091 · doi:10.17760/d20002665

Novel cannabidiol and anandamide analogs

2012· dissertation· en· W2253818091 on OpenAlexaboutno aff
Marsha Rebecca D'Souza

Bibliographic record

Venuenot available
Typedissertation
Languageen
FieldMedicine
TopicCannabis and Cannabinoid Research
Canadian institutionsnot available
Fundersnot available
KeywordsCannabidiolChemistryPharmacologyPharmacophoreCannabinoidCannabinoid receptorAnandamideAnxiolyticCatalepsyIn vivoNeuroprotectionStereochemistryReceptorBiochemistryAntagonistDopamineMedicineBiologyNeuroscienceCannabis

Abstract

fetched live from OpenAlex

Part I: Delta-9-tetrahydrocannabinol (THC) and (-)-cannabidiol (CBD) are the major constituents of Cannabis sativa (marijuana). (-)-CBD shares many of delta-9-THC's therapeutic properties without inducing negative psychotropic effects. These include potential medicinal uses for anti-inflammation, neuroprotection, anxiolytic, anti-nausea and anti-cancer that are all of great therapeutic importance. The clinical potential of (-)-CBD has been realized with the recent approval of Sativex® in Canada, a drug consisting of a 1:1 mixture of delta-9-THC and (-)-CBD for relief of neuropathic and cancer-related pain. Nonetheless, the levorotatory (-)-CBD natural product binds with low affinity to the two principal cannabinoid (CB) G protein-coupled receptors, CB1R and CB2R, whereas the synthetic dextrorotatory (+)-CBD enantiomer binds to both with high (nanomolar) affinity. However, little is known regarding (+)-CBD ligand-binding and functional domains at these receptors, and structure-activity relationship (SAR) data around (+)-CBD is sparse. In this dissertation, a number of high-affinity (+)-CBD analogs have been synthesized in order to explore the SAR. The SAR focused on the side-chain, northern-end, and phenolic hydroxyl pharmacophores of the (+)-CBD prototype. In vitro leads were selected based on their high binding affinity, selectivity as CB2R agonists or CB1R partial agonists, drug-like physicochemical properties, and modulation of in vitro pharmacological activity (cAMP, beta-arrestin assays). These leads were profiled in a panel of rodent paradigms for in vivo cannabinergic activity (hypothermia, catalepsy and tail-flick tests). AM9200 was demonstrated to have a longer duration of action as compared to its metabolite, AM9201, whereas (+)-CBD analogs AM9217 and AM9248 were (weak) partial agonists active in vivo. AM9252 and AM 9222 showed potent analgesic and hypothermic effects in mice and rats, suggesting agonist activity at both CB1R and CB2R. AM 9252 was also shown to have analgesic effects comparable to synthetic delta-9-THC analog (AM 4054) in non-human primates. Also, in order to obtain structural information regarding the binding site of (+)-CBD analogs with these membrane-bound proteins, pharmacologically active (+)-CBD analogs designed as covalent probes to wild-type and mutant CB1R and CB2R are being profiled to help characterize their binding site(s).

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.005
Threshold uncertainty score0.018

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0050.002

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.019
GPT teacher head0.321
Teacher spread0.302 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations0
Published2012
Admission routes1
Has abstractyes

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