A facile method for the preparation of deuterium labeled salvinorin A: Synthesis of [2,2,2- 2H 3]-salvinorin a

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

doi:10.1016/j.bmcl.2004.07.081

A facile method for the preparation of deuterium labeled salvinorin A: Synthesis of [2,2,2- ²H ₃]-salvinorin a

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

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

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.

Original language	English
Pages (from-to)	5099-5102
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	20
DOIs	https://doi.org/10.1016/j.bmcl.2004.07.081
State	Published - Oct 18 2004

Bibliographical note

Funding Information:
The authors thank the College of Pharmacy and the Biological Sciences Funding Program of the University of Iowa for financial support.

Funding

The authors thank the College of Pharmacy and the Biological Sciences Funding Program of the University of Iowa for financial support.

Funders	Funder number
Iowa Environmental Mesonet at Iowa State University

Keywords

Deuterium
Hallucinogen
Salvia divinorum
Salvinorin A

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2004.07.081

Cite this

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title = "A facile method for the preparation of deuterium labeled salvinorin A: Synthesis of [2,2,2- 2H 3]-salvinorin a",

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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author = "Kevin Tidgewell and Harding, \{Wayne W.\} and Mark Schmidt and Holden, \{Kenneth G.\} and Murry, \{Daryl J.\} and \{E. Prisinzano\}, Thomas",

note = "Funding Information: The authors thank the College of Pharmacy and the Biological Sciences Funding Program of the University of Iowa for financial support. ",

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T2 - Synthesis of [2,2,2- 2H 3]-salvinorin a

AU - Tidgewell, Kevin

AU - Harding, Wayne W.

AU - Schmidt, Mark

AU - Holden, Kenneth G.

AU - Murry, Daryl J.

AU - E. Prisinzano, Thomas

N1 - Funding Information: The authors thank the College of Pharmacy and the Biological Sciences Funding Program of the University of Iowa for financial support.

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N2 - 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.

AB - 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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KW - Hallucinogen

KW - Salvia divinorum

KW - Salvinorin A

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