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Digest: Salvinorin A and its Analogs in the Literature Please login to post

Rhodium
(Chief Bee)
09-16-04 22:51
No 492481
User Picture Salvinorin A and its Analogs in the Literature
(Rated as: excellent)

Divinorin A, a Psychotropic Terpenoid, and Divinorin B from the Hallucinogenic Mexican Mint Salvia divinorum
Leander J. Valdes, III, William M. Butler, George M. Hatfield, Ara G. Paul, and Masato Koreeda
J. Org. Chem. 49, 4716-4720 (1984) (https://www.rhodium.ws/pdf/salvinorin-a.joc1984.pdf)
____ ___ __ _

High Performance Liquid Chromatographic Quantification of Salvinorin A from Tissues of Salvia divinorum Epling & Játiva-M
John W. Gruber, Daniel J. Siebert, Ara H. Der Marderosian and Rick S. Hock
Phytochemical Analysis 10, 22-25 (1999) (https://www.rhodium.ws/pdf/salvinorin-a.hplc.pdf)

Abstract
A reversed-phase high performance liquid chromatographic method for the determination of salvinorin A, a psychotropic diterpene isolated from the Mexican sage Salvia divinorum, has been developed. Extracts from several plant collections were examined on a C-18 column with UV detection and isocratic elution with acetonitrile: water (45:55). This assay allowed quantification of salvinorin A in extracts of leaves and stems of S. divinorum and has also been applied to the screening of related species for the production of salvinorin A. Levels of salvinorin A in leaves range from 0.89 to 3.70 mg/g dry weight.
____ ___ __ _

The Absolute Stereochemistry of Salvinorins (Added 05-16-04):
Masato Koreeda, Lindsey Brown, and Leander J. Valdés III
Chemistry Letters 2015-2018 (1990) (https://www.rhodium.ws/pdf/salvinorin.stereochemistry.pdf)

Abstract
The absolute stereostructures of the hallucinogenic diterpenes salvinorin A and B have been unambiguously determined by the use of the non-empirical exciton chirality circular dichroism method on their 1α,2α-diol dibenzoate derivative.
____ ___ __ _

Salvia divinorum: an hallucinogenic mint which might become a new recreational drug in Switzerland
C. Giroud, F. Felber, M. Augsburger, B. Horisberger, L. Rivier, P. Mangin
Forensic Science International 112, 143–150 (2000) (https://www.rhodium.ws/pdf/salvinorin-a.forensic.pdf)
DOI:

Abstract
Salvia divinorum Epling & Jativa is an hallucinogenic mint traditionally used for curing and divination by the Mazatec Indians of Oaxaca, Mexico. Young people from Mexican cities were reported to smoke dried leaves of S. divinorum as a marijuana substitute. Recently, two S. divinorum specimens were seized in a large-scale illicit in-door and out-door hemp plantation. Salvinorin A also called divinorin A, a trans-neoclerodane diterpene, was identified in several organic solvent extracts by gas chromatography–mass spectrometry. The botanical identity of the plant was confirmed by comparing it to an authentic herbarium specimen. More plants were then discovered in Swiss horticulturists greenhouses. All these data taken together suggest that many attempts exist in Switzerland to use S. divinorum as a recreational drug. This phenomenon may be enhanced because neither the magic mint, nor its active compound are banned substances listed in the Swiss narcotic law.
____ ___ __ _

Salvinorin A: A potent naturally occurring nonnitrogenous kappa opioid selective agonist
Bryan L. Roth, Karen Baner, Richard Westkaemper, Daniel Siebert, Kenner C. Rice, SeAnna Steinberg, Paul Ernsberger, and Richard B. Rothman
Proceed. Natl. Acad. Sci. 99(18), 11934–11939 (2002) (https://www.rhodium.ws/pdf/salvinorin-a.pnas.pdf)
DOI:10.1073/pnas.182234399

Abstract
Salvia divinorum, whose main active ingredient is the neoclerodane diterpene Salvinorin A, is a hallucinogenic plant in the mint family that has been used in traditional spiritual practices for its psychoactive properties by the Mazatecs of Oaxaca, Mexico. More recently, S. divinorum extracts and Salvinorin A have become more widely used in the U.S. as legal hallucinogens. We discovered that Salvinorin A potently and selectively inhibited ³H-bremazocine binding to cloned kappa opioid receptors. Salvinorin A had no significant activity against a battery of 50 receptors, transporters, and ion channels and showed a distinctive profile compared with the prototypic hallucinogen lysergic acid diethylamide. Functional studies demonstrated that Salvinorin A is a potent kappa opioid agonist at cloned kappa opioid receptors expressed in human embryonic kidney-293 cells and at native kappa opioid receptors expressed in guinea pig brain. Importantly, Salvinorin A had no actions at the 5-HT_2A serotonin receptor, the principal molecular target responsible for the actions of classical hallucinogens. Salvinorin A thus represents, to our knowledge, the first naturally occurring nonnitrogenous opioid-receptor subtype-selective agonist. Because Salvinorin A is a psychotomimetic selective for kappa opioid receptors, kappa opioid-selective antagonists may represent novel psychotherapeutic compounds for diseases manifested by perceptual distortions (e.g., schizophrenia, dementia, and bipolar disorders). Additionally, these results suggest that kappa opioid receptors play a prominent role in the modulation of human perception.
____ ___ __ _

Salvinorin A: the ‘magic mint’ hallucinogen finds a molecular target in the kappa opioid receptor
Douglas J. Sheffler and Bryan L. Roth
Trends in Pharmacological Sciences 24(3), 107-109 (2003) (https://www.rhodium.ws/pdf/salvinorin-a.kor.pdf)
DOI:10.1016/S0165-6147(03)00027-0

Abstract
Salvinorin A, a neoclerodane diterpene, is the most potent naturally occurring hallucinogen known and rivals the synthetic hallucinogen lysergic acid diethylamide in potency. Recently, the molecular target of salvinorin A was identified as the kappa opioid receptor (KOR). Salvinorin A represents the only known non-nitrogenous KOR selective agonist. Based on the selectivity of salvinorin A for the KOR, this receptor represents a potential molecular target for the development of drugs to treat disorders characterized by alterations in perception, including schizophrenia, Alzheimer’s disease and bipolar disorder.
____ ___ __ _

Salvinorins D-F, New Neoclerodane Diterpenoids from Salvia divinorum, and an Improved Method for the Isolation of Salvinorin A
Thomas A. Munro and Mark A. Rizzacasa
J. Nat. Prod. 66, 703-705 (2003) (https://www.rhodium.ws/pdf/salvinorin-d-f.pdf)
DOI:10.1021/np0205699

Abstract
Three new neoclerodane diterpenoids, salvinorins D-F (4-6), have been isolated from the leaves of Salvia divinorum. The structures were elucidated by chemical and spectroscopic methods, particularly 1D- and 2D-NMR. A simplified isolation method using chromatography on activated carbon also gave improved yields of the controlled substance salvinorin A (1) and of salvinorin C (3).
____ ___ __ _

Divinatorins A-C, New Neoclerodane Diterpenoids from the Controlled Sage Salvia divinorum
Andrea K. Bigham, Thomas A. Munro, Mark A. Rizzacasa, and Roy M. Robins-Browne
J. Nat. Prod. 66, 1242-1244 (2003) (https://www.rhodium.ws/pdf/divinatorins-a-c.pdf)
DOI:10.1021/np030313i

Abstract
Three new neoclerodane diterpenoids, divinatorins A-C (7-9), have been isolated from the leaves of Salvia divinorum. The compounds were identified by spectroscopic methods as derivatives of the antibiotic (-)-hardwickiic acid (10), which was also isolated, along with four other known terpenoids. Neither the crude extract nor 7-9 displayed antimicrobial activity.
____ ___ __ _

A facile method for the preparation of deuterium labeled salvinorin A: Synthesis of [2,2,2-2H3]-salvinorin A latest addition (09-17-04):
Kevin Tidgewell, Wayne W. Harding, Mark Schmidt, Kenneth G. Holden, Daryl J. Murry and Thomas E. Prisinzano
Bioorg. Med. Chem. 14(20), 5099-5102 (2004) DOI:10.1016/j.bmcl.2004.07.081
Full text posted in Post 531635 (Lego: "Synthesis of deuterium labeled Salvinorin A", Novel Discourse)

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.

^{The Hive - Clandestine Chemists Without Borders}

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			Digest: Salvinorin A and its Analogs in the Literature		Please login to post


		Rhodium (Chief Bee) 09-16-04 22:51 No 492481				Salvinorin A and its Analogs in the Literature (Rated as: excellent)
						Divinorin A, a Psychotropic Terpenoid, and Divinorin B from the Hallucinogenic Mexican Mint Salvia divinorum Leander J. Valdes, III, William M. Butler, George M. Hatfield, Ara G. Paul, and Masato Koreeda J. Org. Chem. 49, 4716-4720 (1984) (https://www.rhodium.ws/pdf/salvinorin-a.joc1984.pdf) ____ ___ __ _ *High Performance Liquid Chromatographic Quantification of Salvinorin A from Tissues of Salvia divinorum* Epling & Játiva-M** John W. Gruber, Daniel J. Siebert, Ara H. Der Marderosian and Rick S. Hock Phytochemical Analysis 10, 22-25 (1999) (https://www.rhodium.ws/pdf/salvinorin-a.hplc.pdf) Abstract A reversed-phase high performance liquid chromatographic method for the determination of salvinorin A, a psychotropic diterpene isolated from the Mexican sage Salvia divinorum, has been developed. Extracts from several plant collections were examined on a C-18 column with UV detection and isocratic elution with acetonitrile: water (45:55). This assay allowed quantification of salvinorin A in extracts of leaves and stems of S. divinorum and has also been applied to the screening of related species for the production of salvinorin A. Levels of salvinorin A in leaves range from 0.89 to 3.70 mg/g dry weight. ____ ___ __ _ The Absolute Stereochemistry of Salvinorins (Added 05-16-04): Masato Koreeda, Lindsey Brown, and Leander J. Valdés III Chemistry Letters 2015-2018 (1990) (https://www.rhodium.ws/pdf/salvinorin.stereochemistry.pdf) Abstract The absolute stereostructures of the hallucinogenic diterpenes salvinorin A and B have been unambiguously determined by the use of the non-empirical exciton chirality circular dichroism method on their 1α,2α-diol dibenzoate derivative. ____ ___ __ _ Salvia divinorum: an hallucinogenic mint which might become a new recreational drug in Switzerland C. Giroud, F. Felber, M. Augsburger, B. Horisberger, L. Rivier, P. Mangin Forensic Science International 112, 143–150 (2000) (https://www.rhodium.ws/pdf/salvinorin-a.forensic.pdf) DOI: Abstract Salvia divinorum Epling & Jativa is an hallucinogenic mint traditionally used for curing and divination by the Mazatec Indians of Oaxaca, Mexico. Young people from Mexican cities were reported to smoke dried leaves of S. divinorum as a marijuana substitute. Recently, two S. divinorum specimens were seized in a large-scale illicit in-door and out-door hemp plantation. Salvinorin A also called divinorin A, a trans-neoclerodane diterpene, was identified in several organic solvent extracts by gas chromatography–mass spectrometry. The botanical identity of the plant was confirmed by comparing it to an authentic herbarium specimen. More plants were then discovered in Swiss horticulturists greenhouses. All these data taken together suggest that many attempts exist in Switzerland to use S. divinorum as a recreational drug. This phenomenon may be enhanced because neither the magic mint, nor its active compound are banned substances listed in the Swiss narcotic law. ____ ___ __ _ Salvinorin A: A potent naturally occurring nonnitrogenous kappa opioid selective agonist Bryan L. Roth, Karen Baner, Richard Westkaemper, Daniel Siebert, Kenner C. Rice, SeAnna Steinberg, Paul Ernsberger, and Richard B. Rothman Proceed. Natl. Acad. Sci. 99(18), 11934–11939 (2002) (https://www.rhodium.ws/pdf/salvinorin-a.pnas.pdf) DOI:10.1073/pnas.182234399 Abstract Salvia divinorum, whose main active ingredient is the neoclerodane diterpene Salvinorin A, is a hallucinogenic plant in the mint family that has been used in traditional spiritual practices for its psychoactive properties by the Mazatecs of Oaxaca, Mexico. More recently, S. divinorum extracts and Salvinorin A have become more widely used in the U.S. as legal hallucinogens. We discovered that Salvinorin A potently and selectively inhibited ³H-bremazocine binding to cloned kappa opioid receptors. Salvinorin A had no significant activity against a battery of 50 receptors, transporters, and ion channels and showed a distinctive profile compared with the prototypic hallucinogen lysergic acid diethylamide. Functional studies demonstrated that Salvinorin A is a potent kappa opioid agonist at cloned kappa opioid receptors expressed in human embryonic kidney-293 cells and at native kappa opioid receptors expressed in guinea pig brain. Importantly, Salvinorin A had no actions at the 5-HT_2A serotonin receptor, the principal molecular target responsible for the actions of classical hallucinogens. Salvinorin A thus represents, to our knowledge, the first naturally occurring nonnitrogenous opioid-receptor subtype-selective agonist. Because Salvinorin A is a psychotomimetic selective for kappa opioid receptors, kappa opioid-selective antagonists may represent novel psychotherapeutic compounds for diseases manifested by perceptual distortions (e.g., schizophrenia, dementia, and bipolar disorders). Additionally, these results suggest that kappa opioid receptors play a prominent role in the modulation of human perception. ____ ___ __ _ Salvinorin A: the ‘magic mint’ hallucinogen finds a molecular target in the kappa opioid receptor Douglas J. Sheffler and Bryan L. Roth Trends in Pharmacological Sciences 24(3), 107-109 (2003) (https://www.rhodium.ws/pdf/salvinorin-a.kor.pdf) DOI:10.1016/S0165-6147(03)00027-0 Abstract Salvinorin A, a neoclerodane diterpene, is the most potent naturally occurring hallucinogen known and rivals the synthetic hallucinogen lysergic acid diethylamide in potency. Recently, the molecular target of salvinorin A was identified as the kappa opioid receptor (KOR). Salvinorin A represents the only known non-nitrogenous KOR selective agonist. Based on the selectivity of salvinorin A for the KOR, this receptor represents a potential molecular target for the development of drugs to treat disorders characterized by alterations in perception, including schizophrenia, Alzheimer’s disease and bipolar disorder. ____ ___ __ _ *Salvinorins D-F, New Neoclerodane Diterpenoids from Salvia divinorum, and an Improved Method for the Isolation of Salvinorin A* Thomas A. Munro and Mark A. Rizzacasa J. Nat. Prod. 66, 703-705 (2003) (https://www.rhodium.ws/pdf/salvinorin-d-f.pdf) DOI:10.1021/np0205699 Abstract Three new neoclerodane diterpenoids, salvinorins D-F (4-6), have been isolated from the leaves of Salvia divinorum. The structures were elucidated by chemical and spectroscopic methods, particularly 1D- and 2D-NMR. A simplified isolation method using chromatography on activated carbon also gave improved yields of the controlled substance salvinorin A (1) and of salvinorin C (3). ____ ___ __ _ Divinatorins A-C, New Neoclerodane Diterpenoids from the Controlled Sage Salvia divinorum Andrea K. Bigham, Thomas A. Munro, Mark A. Rizzacasa, and Roy M. Robins-Browne J. Nat. Prod. 66, 1242-1244 (2003) (https://www.rhodium.ws/pdf/divinatorins-a-c.pdf) DOI:10.1021/np030313i Abstract Three new neoclerodane diterpenoids, divinatorins A-C (7-9), have been isolated from the leaves of Salvia divinorum. The compounds were identified by spectroscopic methods as derivatives of the antibiotic (-)-hardwickiic acid (10), which was also isolated, along with four other known terpenoids. Neither the crude extract nor 7-9 displayed antimicrobial activity. ____ ___ __ _ A facile method for the preparation of deuterium labeled salvinorin A: Synthesis of [2,2,2-2H3]-salvinorin A (09-17-04): Kevin Tidgewell, Wayne W. Harding, Mark Schmidt, Kenneth G. Holden, Daryl J. Murry and Thomas E. Prisinzano Bioorg. Med. Chem. 14(20), 5099-5102 (2004) DOI:10.1016/j.bmcl.2004.07.081 Full text posted in Post 531635 (Lego: "Synthesis of deuterium labeled Salvinorin A", Novel Discourse) 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. ^{The Hive - Clandestine Chemists Without Borders}