Literature DB >> 17919913

Synthesis and pharmacology of 1-deoxy analogs of CP-47,497 and CP-55,940.

John W Huffman1, Alicia L S Thompson, Jenny L Wiley, Billy R Martin.   

Abstract

A series of 1-deoxy analogs of CP-47,497 (8 and 13, n=0-7) and 1-deoxy analogs of CP-55,940 (9, n=0-7) have been synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors have been determined. Although the majority of these compounds exhibit selectivity for the CB(2) receptor, none have greater than modest affinity for either receptor. The interactions of these 1-deoxy nontraditional cannabinoids with the CB(2) receptor are discussed.

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Year:  2007        PMID： 17919913      PMCID： PMC2262798          DOI： 10.1016/j.bmc.2007.09.033

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  48 in total

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Authors:  T P Malan; M M Ibrahim; H Deng; Q Liu; H P Mata; T Vanderah; F Porreca; A Makriyannis
Journal:  Pain       Date:  2001-09       Impact factor: 6.961

Review 2.  Targeting the endocannabinoid system in cancer therapy: a call for further research.

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Journal:  Nat Med       Date:  2002-06       Impact factor: 53.440

3.  Immunomodulation by cannabinoids is absent in mice deficient for the cannabinoid CB(2) receptor.

Authors:  N E Buckley; K L McCoy; E Mezey; T Bonner; A Zimmer; C C Felder; M Glass; A Zimmer
Journal:  Eur J Pharmacol       Date:  2000-05-19       Impact factor: 4.432

4.  1-Methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: new selective ligands for the CB2 receptor.

Authors:  John W Huffman; Simon M Bushell; John R A Miller; Jenny L Wiley; Billy R Martin
Journal:  Bioorg Med Chem       Date:  2002-12       Impact factor: 3.641

Review 5.  The search for selective ligands for the CB2 receptor.

Authors:  J W Huffman
Journal:  Curr Pharm Des       Date:  2000-09       Impact factor: 3.116

6.  HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor.

Authors:  L Hanus; A Breuer; S Tchilibon; S Shiloah; D Goldenberg; M Horowitz; R G Pertwee; R A Ross; R Mechoulam; E Fride
Journal:  Proc Natl Acad Sci U S A       Date:  1999-12-07       Impact factor: 11.205

7.  Antiinflammatory action of endocannabinoid palmitoylethanolamide and the synthetic cannabinoid nabilone in a model of acute inflammation in the rat.

Authors:  Silvia Conti; Barbara Costa; Mariapia Colleoni; Daniela Parolaro; Gabriella Giagnoni
Journal:  Br J Pharmacol       Date:  2002-01       Impact factor: 8.739

8.  Functional role of tryptophan residues in the fourth transmembrane domain of the CB(2) cannabinoid receptor.

Authors:  M H Rhee; I Nevo; M L Bayewitch; O Zagoory; Z Vogel
Journal:  J Neurochem       Date:  2000-12       Impact factor: 5.372

9.  CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain.

Authors:  N Clayton; F H Marshall; C Bountra; C T O'Shaughnessy
Journal:  Pain       Date:  2002-04       Impact factor: 6.961

10.  Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain.

Authors:  Gerard M P Giblin; Celestine T O'Shaughnessy; Alan Naylor; William L Mitchell; Andrew J Eatherton; Brian P Slingsby; D Anthony Rawlings; Paul Goldsmith; Andrew J Brown; Carl P Haslam; Nick M Clayton; Alex W Wilson; Iain P Chessell; Andrew R Wittington; Richard Green
Journal:  J Med Chem       Date:  2007-05-04       Impact factor: 7.446
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  11 in total

1.  Constitutive activity at the cannabinoid CB(1) receptor and behavioral responses.

Authors:  Katherine E Hanlon; Todd W Vanderah
Journal:  Methods Enzymol       Date:  2010       Impact factor: 1.600

2.  CB1 receptor-mediated signaling underlies the hippocampal synaptic, learning, and memory deficits following treatment with JWH-081, a new component of spice/K2 preparations.

Authors:  Balapal S Basavarajappa; Shivakumar Subbanna
Journal:  Hippocampus       Date:  2014-02       Impact factor: 3.899

Review 3.  Distinct pharmacology and metabolism of K2 synthetic cannabinoids compared to Δ(9)-THC: mechanism underlying greater toxicity?

Authors:  William E Fantegrossi; Jeffery H Moran; Anna Radominska-Pandya; Paul L Prather
Journal:  Life Sci       Date:  2013-09-29       Impact factor: 5.037

4.  JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB receptor agonist.

Authors:  Brady K Atwood; John Huffman; Alex Straiker; Ken Mackie
Journal:  Br J Pharmacol       Date:  2010-01-22       Impact factor: 8.739

Review 5.  Pharmacological and Toxicological Effects of Synthetic Cannabinoids and Their Metabolites.

Authors:  Sherrica Tai; William E Fantegrossi
Journal:  Curr Top Behav Neurosci       Date:  2017

6.  Synthesis and pharmacology of 1-methoxy analogs of CP-47,497.

Authors:  John W Huffman; Seon A Hepburn; Patricia H Reggio; Dow P Hurst; Jenny L Wiley; Billy R Martin
Journal:  Bioorg Med Chem       Date:  2010-06-22       Impact factor: 3.641

7.  Evaluation of a homogenous enzyme immunoassay for the detection of synthetic cannabinoids in urine.

Authors:  Allan J Barnes; Sheena Young; Eliani Spinelli; Thomas M Martin; Kevin L Klette; Marilyn A Huestis
Journal:  Forensic Sci Int       Date:  2014-04-24       Impact factor: 2.395

8.  Comparison of the discriminative stimulus and response rate effects of Δ9-tetrahydrocannabinol and synthetic cannabinoids in female and male rats.

Authors:  Jenny L Wiley; Timothy W Lefever; Julie A Marusich; Rebecca M Craft
Journal:  Drug Alcohol Depend       Date:  2017-01-11       Impact factor: 4.492

9.  Development of a high-performance liquid chromatography-tandem mass spectrometry method for the identification and quantification of CP-47,497, CP-47,497-C8 and JWH-250 in mouse brain.

Authors:  Kimberly L Samano; Justin L Poklis; Aron H Lichtman; Alphonse Poklis
Journal:  J Anal Toxicol       Date:  2014-05-09       Impact factor: 3.367

10.  Beyond THC: The New Generation of Cannabinoid Designer Drugs.

Authors:  Liana Fattore; Walter Fratta
Journal:  Front Behav Neurosci       Date:  2011-09-21       Impact factor: 3.558
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