Literature DB >> 15380207

A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A.

Kevin Tidgewell1, Wayne W Harding, Mark Schmidt, Kenneth G Holden, Daryl J Murry, Thomas E Prisinzano.   

Abstract

Salvinorin A is a novel hallucinogen isolated from the widely available leaves of Salvia divinorum. Based on its mechanism of action, salvinorin A has shown potential as a stimulant abuse therapeutic. However, there are no methods for the detection of salvinorin A or its metabolites in biological fluids. In order to begin developing salvinorin A as a potential therapeutic, an understanding of its metabolism is needed. Here, a straightforward synthesis of a deuterium labeled analog of salvinorin A and its utility as an internal standard for the detection of salvinorin A and its metabolites in biological fluids by LC-MS is described.

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Year:  2004        PMID: 15380207     DOI: 10.1016/j.bmcl.2004.07.081

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  30 in total

1.  Autoxidation of salvinorin A under basic conditions.

Authors:  Thomas A Munro; Glenn W Goetchius; Bryan L Roth; Timothy A Vortherms; Mark A Rizzacasa
Journal:  J Org Chem       Date:  2005-11-25       Impact factor: 4.354

2.  Salvinorin A and derivatives: protection from metabolism does not prolong short-term, whole-brain residence.

Authors:  Jacob M Hooker; Thomas A Munro; Cécile Béguin; David Alexoff; Colleen Shea; Youwen Xu; Bruce M Cohen
Journal:  Neuropharmacology       Date:  2009-07-08       Impact factor: 5.250

3.  Potential Drug Abuse Therapeutics Derived from the Hallucinogenic Natural Product Salvinorin A.

Authors:  Katherine M Prevatt-Smith; Kimberly M Lovell; Denise S Simpson; Victor W Day; Justin T Douglas; Peter Bosch; Christina M Dersch; Richard B Rothman; Bronwyn Kivell; Thomas E Prisinzano
Journal:  Medchemcomm       Date:  2011-12       Impact factor: 3.597

Review 4.  Neoclerodanes as atypical opioid receptor ligands.

Authors:  Thomas E Prisinzano
Journal:  J Med Chem       Date:  2013-04-18       Impact factor: 7.446

5.  Impact of Pharmacological Manipulation of the κ-Opioid Receptor System on Self-grooming and Anhedonic-like Behaviors in Male Mice.

Authors:  Eduardo R Butelman; Bryan D McElroy; Thomas E Prisinzano; Mary Jeanne Kreek
Journal:  J Pharmacol Exp Ther       Date:  2019-04-11       Impact factor: 4.030

6.  LC-MS/MS quantification of salvinorin A from biological fluids.

Authors:  Michael J Caspers; Todd D Williams; Kimberly M Lovell; Anthony Lozama; Eduardo R Butelman; Mary Jeanne Kreek; Matthew Johnson; Roland Griffiths; Katherine Maclean; Thomas E Prisinzano
Journal:  Anal Methods       Date:  2013-12-21       Impact factor: 2.896

Review 7.  Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A.

Authors:  Christopher W Cunningham; Richard B Rothman; Thomas E Prisinzano
Journal:  Pharmacol Rev       Date:  2011-03-28       Impact factor: 25.468

8.  Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers.

Authors:  Thomas A Munro; Katharine K Duncan; Wei Xu; Yulin Wang; Lee-Yuan Liu-Chen; William A Carlezon; Bruce M Cohen; Cécile Béguin
Journal:  Bioorg Med Chem       Date:  2007-10-24       Impact factor: 3.641

9.  Herkinorin analogues with differential beta-arrestin-2 interactions.

Authors:  Kevin Tidgewell; Chad E Groer; Wayne W Harding; Anthony Lozama; Matthew Schmidt; Alfred Marquam; Jessica Hiemstra; John S Partilla; Christina M Dersch; Richard B Rothman; Laura M Bohn; Thomas E Prisinzano
Journal:  J Med Chem       Date:  2008-04-02       Impact factor: 7.446

10.  Synthetic studies of neoclerodane diterpenes from Salvia divinorum: role of the furan in affinity for opioid receptors.

Authors:  Denise S Simpson; Kimberly M Lovell; Anthony Lozama; Nina Han; Victor W Day; Christina M Dersch; Richard B Rothman; Thomas E Prisinzano
Journal:  Org Biomol Chem       Date:  2009-07-14       Impact factor: 3.876

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