Evidence map›Paper›PMID 27367336›Full record

ArticleJournal of medicinal chemistry2016

Novel C-Ring-Hydroxy-Substituted Controlled Deactivation Cannabinergic Analogues.

Shashank Kulkarni, Spyros P Nikas, Rishi Sharma, Shan Jiang, Carol A Paronis, Michael Z Leonard, Bin Zhang, Chandrashekhar Honrao, Srikrishnan Mallipeddi, Jimit Girish Raghav and 4 more

Abstract read
In one paragraph

Article in Journal of medicinal chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

10 citing papers in PubMed.

  1. Article
  2. Review
  3. Review
  4. Article
  5. Synthesis of Functionalized Cannabilactones.Molecules (Basel, Switzerland) · 2020
    Article
  6. Article
  7. Article
  8. Article
  9. Preclinical Studies of Cannabinoid Reward, Treatments for Cannabis Use Disorder, and Addiction-Related Effects of Cannabinoid Exposure.Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology · 2018
    Review
  10. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

14 authors.

Shashank KulkarniCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Spyros P NikasCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Rishi SharmaCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Shan JiangCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Carol A ParonisCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Michael Z LeonardMcLean Hospital, and Harvard Medical School, Belmont, Massachusetts 02478, United States.
Bin ZhangCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Chandrashekhar HonraoCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Srikrishnan MallipeddiCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Jimit Girish RaghavCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Othman BenchamaCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Torbjörn U C JärbeCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.
Jack BergmanMcLean Hospital, and Harvard Medical School, Belmont, Massachusetts 02478, United States.
Alexandros MakriyannisCenter for Drug Discovery, Department of Chemistry and Chemical Biology, and Department of Pharmaceutical Sciences, Northeastern University , Boston, Massachusetts 02115, United States.

Funding

Project 3 - In vivo pharmacology of cannabinoid receptor probesP01DA009158 · NIDA · UNIVERSITY OF CONNECTICUT STORRS · PI Alexandros Makriyannis · 1994 to 2026
$26.0M
CANNABINOID LIGANDS AND DRUGSR01DA007215 · NIDA · UNIVERSITY OF CONNECTICUT STORRS · PI MAKRIYANNIS, ALEXANDROS · 1993 to 2012
$3.6M
Exogenous/endogenous cannabinoids--A comparisonR01DA009064 · NIDA · TEMPLE UNIVERSITY · PI MAKRIYANNIS, ALEXANDROS · 1995 to 2016
$3.2M
Novel Medications for Cannabis DependenceR01DA026795 · NIDA · NORTHEASTERN UNIVERSITY · PI MAKRIYANNIS, ALEXANDROS · 2009 to 2013
$2.8M
MOLECULAR BASIS OF CANNABINOID ACTIVITYR01DA003801 · NIDA · UNIVERSITY OF CONNECTICUT STORRS · PI MAKRIYANNIS, ALEXANDROS · 1985 to 2017
$2.5M
NIDA NIH HHS P01 DA009158NIDA NIH HHS R01 DA003801NIDA NIH HHS R01 DA007215NIDA NIH HHS R01 DA009064NIDA NIH HHS R01 DA026795
6 · The paper itself

Abstract

In pursuit of safer controlled-deactivation cannabinoids with high potency and short duration of action, we report the design, synthesis, and pharmacological evaluation of novel C9- and C11-hydroxy-substituted hexahydrocannabinol (HHC) and tetrahydrocannabinol (THC) analogues in which a seven atom long side chain, with or without 1'-substituents, carries a metabolically labile 2',3'-ester group. Importantly, in vivo studies validated our controlled deactivation approach in rodents and non-human primates. The lead molecule identified here, namely, butyl-2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-3-yl]-2-methylpropanoate (AM7499), was found to exhibit remarkably high in vitro and in vivo potency with shorter duration of action than the currently existing classical cannabinoid agonists.

Indexed as

AnimalsCannabinoid Receptor AgonistsCannabinolDose-Response Relationship, DrugFemaleHEK293 CellsHumansMaleMiceMolecular StructureRatsRats, Sprague-DawleyReceptors, CannabinoidSaimiriStructure-Activity RelationshipCannabinoid Receptor AgonistsCannabinolReceptors, Cannabinoid

Identifiers

PMID27367336
PMCPMC5532543

What OpenQuestion holds

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.