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Jordan K. Zjawiony - One of the best experts on this subject based on the ideXlab platform.
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The Plant Salvia Divinorum (Lamiaceae)—Chemistry and Pharmacology
Neuropathology of Drug Addictions and Substance Misuse, 2016Co-Authors: Adam W. Keasling, Jordan K. ZjawionyAbstract:Abstract The plant Salvia Divinorum (Epling & Jativa-M.) is a member of the mint family (Lamiaceae) endemic to the Sierra Mazateca region of the Sierra Madre de Oaxaca of southern Mexico. It has a history of known ethnobotanical use by the Mazatec Indians extending several centuries both in medicinal and spiritual practices. Reports of the perceptiotropic effects that accompanied use of this material led to phytochemical investigations which yielded a novel neoclerodane diterpenoid, salvinorin A. This compound was found to possess extremely high affinity and selectivity for the kappa opioid receptors and was determined to bind in a unique manner different from classic opioids. While S. Divinorum and salvinorin A both produce pronounced perceptotropic effects (i.e., mixed hallucinogenic and dissociative effects) they have also been shown to attenuate drug-seeking behavior. Furthermore, salvinorin A has been repeatedly shown to possess an extremely low potential for physiological toxicity. Salvia Divinorum represents a novel source of bioactive molecules some of which have been shown to have utility as antiaddiction therapeutics.
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Vegetative anatomy and micromorphology of Salvia Divinorum (Lamiaceae) from Mexico, combined with chromatographic analysis of salvinorin A
Journal of Natural Medicines, 2014Co-Authors: Anna P. Kowalczuk, Ikhlas A. Khan, Daniel J. Siebert, Vijayasankar Raman, Ahmed M. Galal, Jordan K. ZjawionyAbstract:Salvia Divinorum —a species traditionally cultivated in Oaxaca, Mexico—possesses hallucinogenic properties. It is legally recognized as a controlled substance and prohibited in many countries. The proper identification of the plant, both in fresh and dried forms, is an important issue in crime-prevention campaigns. This paper provides a thorough anatomical description of leaves, petioles, and stems of S. Divinorum . Detailed investigation of foliar trichomes was performed and illustrated. In addition, chromatographic analyses, including TLC and HPLC, were applied to fresh and dried plant material, together with the standard reference salvinorin A. A comprehensive identification method for S. Divinorum based on a thorough anatomical examination is proposed, combined with chemical analysis for proper plant recognition.
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The effect of Salvia Divinorum and Mitragyna speciosa extracts, fraction and major constituents on place aversion and place preference in rats
Journal of ethnopharmacology, 2013Co-Authors: Kenneth J. Sufka, Jordan K. Zjawiony, Melissa J. Loria, Kevin Lewellyn, Zulfiqar Ali, N Abe, Ikhlas A. KhanAbstract:Abstract Ethnopharmacological relevance Consumer use of botanicals has increased despite, in many instances, the paucity of research demonstrating efficacy or identifying liabilities. This research employed the place preference/aversion paradigm to characterize the psychoactive properties of Salvia Divinorum extract (10, 30, 100 mg/kg), salvinorin A (0.1, 0.3, 1.0 mg/kg), Mitragyna speciosa MeOH extract (50, 100, 300 mg/kg), Mitragyna speciosa alkaloid-enriched fraction (12.5, 25, 75 mg/kg) and mitragynine (5, 10, 30 mg/kg) in rats. Material and methods Following apparatus habituation and baseline preference scores, male Sprague-Dawley rats were given eight counter-balanced drug versus vehicle conditioning trials followed by a preference test conducted under drug-free states. S ( + )-amphetamine (1 mg/kg) served as the positive control (in Exp. 2) and haloperidol (0.8, 1.0 mg/kg) served as the negative control in both studies. Results Rats displayed place aversion to both Salvia Divinorum and salvinorin A that exceeded that of haloperidol. Rats showed place preference to mitragynine that was similar to that of S ( + ) - amphetamine. This CPP effect was much less pronounced with the Mitragyna speciosa extract and its fraction. Conclusions These findings suggest that both botanicals possess liabilities, albeit somewhat different, that warrant caution in their use.
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Salvinorins J from Salvia Divinorum: mutarotation in the neoclerodane system.
Journal of natural products, 2009Co-Authors: L Kutrzeba, Daneel Ferreira, Jordan K. ZjawionyAbstract:A search for biosynthetic precursors of salvinorin A (1) led to the isolation of a new neoclerodane diterpenoid hemiacetal mixture, salvinorins J (2), from the chloroform extract of Salvia Divinorum. A leaf surface extraction method was used on S. Divinorum, affording a chlorophyll-free extract containing predominantly neoclerodane diterpenoids, including the new salvinorins J (2) and 14 known analogues. Salvinorins J (2) represent an example of a neoclerodane hemiacetal (lactol) susceptible to mutarotation with the formation of an equilibrium mixture of C-17 epimers.
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inhibitory effect of salvinorin a from Salvia Divinorum on ileitis induced hypermotility cross talk between κ opioid and cannabinoid cb1 receptors
British Journal of Pharmacology, 2009Co-Authors: Roberta Capasso, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Maria Grazia Cascio, K Huben, P Marini, Barbara Romano, V. Di Marzo, Francesco CapassoAbstract:Background and purpose: Salvinorin A, the active component of the hallucinogenic herb Salvia Divinorum, inhibits intestinal motility through activation of κ-opioid receptors (KORs). However, this compound may have target(s) other than the KORs in the inflamed gut. Because intestinal inflammation upregulates cannabinoid receptors and endogenous cannabinoids, in the present study we investigated the possible involvement of the endogenous cannabinoid system in salvinorin A-induced delay in motility in the inflamed gut.
Michael Heinrich - One of the best experts on this subject based on the ideXlab platform.
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from local to global fifty years of research on Salvia Divinorum
Journal of Ethnopharmacology, 2014Co-Authors: Ivan Casselman, Catherine J Nock, Hans Wohlmuth, Robert P Weatherby, Michael HeinrichAbstract:Abstract Ethnopharmacological relevance In 1962 ethnopharmacologists, Hofmann and Wasson, undertook an expedition to Oaxaca, Mexico. These two researchers were the first scientists to collect a flowering specimen of Salvia Divinorum allowing the identification of this species. While the species' traditional use is confined to a very small region of Mexico, since Hofmann and Wasson's expedition 50 years ago, Salvia Divinorum has become globally recognized for its main active constituent, the diterpene salvinorin A, which has a unique effect on human physiology. Salvinorin A is a kappa-opioid agonist and the first reported psychoactive diterpene. Methods This review concentrates on the investigation of Salvia Divinorum over the last 50 years including ethnobotany, ethnopharmacology, taxonomy, systematics, genetics, chemistry and pharmacodynamic and pharmacokinetic research. For the purpose of this review, online search engines were used to find relevant research. Searches were conducted between October 2011 and September 2013 using the search term “ Salvia Divinorum ”. Papers were excluded if they described synthetic chemical synthesis of salvinorin A or analogues. Results Ethnobotanically there is a comprehensive body of research describing the traditional Mazatec use of the plant, however, the modern ethnobotanical use of this plant is not well documented. There are a limited number of botanical investigations into this plant and there are still several aspects of the botany of Salvia Divinorum which need further investigation. One study has investigated the phylogenetic relationship of Salvia Divinorum to other species in the genus. To date the main focus of chemistry research on Salvia Divinorum has been salvinorin A, the main active compound in Salvia Divinorum , and other related diterpenoids. Finally, the effects of salvinorin A, a KOR agonist, have primarily been investigated using animal models. Conclusions As Salvia Divinorum use increases worldwide, the emerging cultural use patterns will warrant more research. More botanical information is also needed to better understand this species, including germination, pollination vector and a better understanding of the endemic environment of Salvia Divinorum . As well there is a gap in the genetic knowledge of this species and very little is known about its intra-species genetics. The terpenes in Salvia Divinorum are very well documented, however, other classes of constituents in this species warrant further investigation and identification. To date, the majority of the pharmacology research on Salvia Divinorum has focused on the effects of salvinorin A using animal models. Published human studies have not reported any harmful effects when salvinorin A is administered within the dose range of 0.375–21 µg/kg but what are the implications when applied to a larger population? More data on the toxicology and safety of Salvia Divinorum are needed before larger scale clinical trials of the potential therapeutic effects of Salvia Divinorum and salvinorin A are undertaken.
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From local to global—Fifty years of research on Salvia Divinorum
Journal of ethnopharmacology, 2013Co-Authors: Ivan Casselman, Catherine J Nock, Hans Wohlmuth, Robert P Weatherby, Michael HeinrichAbstract:Abstract Ethnopharmacological relevance In 1962 ethnopharmacologists, Hofmann and Wasson, undertook an expedition to Oaxaca, Mexico. These two researchers were the first scientists to collect a flowering specimen of Salvia Divinorum allowing the identification of this species. While the species' traditional use is confined to a very small region of Mexico, since Hofmann and Wasson's expedition 50 years ago, Salvia Divinorum has become globally recognized for its main active constituent, the diterpene salvinorin A, which has a unique effect on human physiology. Salvinorin A is a kappa-opioid agonist and the first reported psychoactive diterpene. Methods This review concentrates on the investigation of Salvia Divinorum over the last 50 years including ethnobotany, ethnopharmacology, taxonomy, systematics, genetics, chemistry and pharmacodynamic and pharmacokinetic research. For the purpose of this review, online search engines were used to find relevant research. Searches were conducted between October 2011 and September 2013 using the search term “ Salvia Divinorum ”. Papers were excluded if they described synthetic chemical synthesis of salvinorin A or analogues. Results Ethnobotanically there is a comprehensive body of research describing the traditional Mazatec use of the plant, however, the modern ethnobotanical use of this plant is not well documented. There are a limited number of botanical investigations into this plant and there are still several aspects of the botany of Salvia Divinorum which need further investigation. One study has investigated the phylogenetic relationship of Salvia Divinorum to other species in the genus. To date the main focus of chemistry research on Salvia Divinorum has been salvinorin A, the main active compound in Salvia Divinorum , and other related diterpenoids. Finally, the effects of salvinorin A, a KOR agonist, have primarily been investigated using animal models. Conclusions As Salvia Divinorum use increases worldwide, the emerging cultural use patterns will warrant more research. More botanical information is also needed to better understand this species, including germination, pollination vector and a better understanding of the endemic environment of Salvia Divinorum . As well there is a gap in the genetic knowledge of this species and very little is known about its intra-species genetics. The terpenes in Salvia Divinorum are very well documented, however, other classes of constituents in this species warrant further investigation and identification. To date, the majority of the pharmacology research on Salvia Divinorum has focused on the effects of salvinorin A using animal models. Published human studies have not reported any harmful effects when salvinorin A is administered within the dose range of 0.375–21 µg/kg but what are the implications when applied to a larger population? More data on the toxicology and safety of Salvia Divinorum are needed before larger scale clinical trials of the potential therapeutic effects of Salvia Divinorum and salvinorin A are undertaken.
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Novel use patterns of Salvia Divinorum: unobtrusive observation using YouTube™.
Journal of ethnopharmacology, 2011Co-Authors: Ivan Casselman, Michael HeinrichAbstract:Abstract Ethnopharmacological relevance and Aims The traditional use of the Hallucinogenic sage, Salvia Divinorum has been of ethnopharmalogical interest for some time. This plant, endemic to Oaxaca Mexico and traditionally used by the Mazatec, is now utilized worldwide for its psychoactive effects. This use demonstrates a novel use pattern which is distinctly different from Mazatec use. This study offers a new methodology to study emerging global plant use and assesses the users’ experience with it. The aim of this research was to develop a new methodology to collect and analyze archived data on the World Wide Web, specifically videos which depict Salvia Divinorum use. Methods The basis of the methodology for this project was unobtrusive observation which allows the researcher to observe without influencing the event which is being observed. Qualitative, ethnographic data was used in conjunction with quantitative meta data collected by a customized web crawler programed to archive YouTube™ data. Results Using this methodology enabled us to understand reported uses and the users’ experiences as expressed on the World Wide Web. The main result of this research was the documentation of a distinct, novel use pattern of Salvia Divinorum which has developed outside of Oaxaca; a use pattern which differs in a number of ways from traditional, Mazatec use. The majority of the YouTube™ videos analyzed were found to present indications of a positive Salvia Divinorum experience. This result highlighted the contradiction between ethnographic data and what is reported by the media. Finally the representation of Salvia Divinorum on YouTube™ (and by inference the WWW as a whole) is a growing phenomena. Conclusions While anthropological and more specifically medico-anthropological research has, for many years, embraced the dynamics of cultures, until recently, ethnopharmalogical research has generally focused on ‘traditional’ plant use, failing to capture the dynamic elements of plant/human interaction and framing research in the past or as decontextualized largely descriptive reports. Global migration and urban environments formed a basis for looking at the interplay of continuity and change. Such cultural dynamics are exacerbated by the opportunities which the WWW offers.
Thomas E Prisinzano - One of the best experts on this subject based on the ideXlab platform.
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Palladium-Catalyzed Transformations of Salvinorin A, a Neoclerodane Diterpene from Salvia Divinorum
Organic letters, 2013Co-Authors: Andrew Philip Riley, Victor W. Day, Hernán A. Navarro, Thomas E PrisinzanoAbstract:Transformations that selectively modify the furan ring present in a variety of naturals products would be useful in the synthesis of biological probes but remain largely underexplored. The neoclerodane diterpene salvinorin A, isolated from Salvia Divinorum, is an example of a furan-containing natural product. Following selective bromination of salvinorin A, Suzuki–Miyaura and Sonogashira couplings were accomplished in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of the epimerizable centers.
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psychopharmacology of the hallucinogenic sage Salvia Divinorum
Life Sciences, 2005Co-Authors: Thomas E PrisinzanoAbstract:Abstract At present, the Mexican mint Salvia Divinorum is an unregulated hallucinogen. This has resulted in various on-line botanical companies advertising and selling S. Divinorum as a legal alternative to other regulated plant hallucinogens. It is predictable that its misuse will increase rapidly. The active ingredient in S. Divinorum is the neoclerodane diterpene, salvinorin A ( 1a ), which has been shown to be a κ agonist both in vitro and in vivo. This review will cover the current state of research into the psychopharmacology of S. Divinorum .
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Salvinicins A and B, new neoclerodane diterpenes from Salvia Divinorum.
Organic letters, 2005Co-Authors: Wayne W. Harding, Kevin Tidgewell, Matthew Schmidt, Kushal Shah, Christina M. Dersch, John K. Snyder, Damon A. Parrish, Jeffrey R. Deschamps, Richard B. Rothman, Thomas E PrisinzanoAbstract:Two new neoclerodane diterpenes, salvinicins A (4) and B (5), were isolated from the dried leaves of Salvia Divinorum. The structures of these compounds were elucidated by spectroscopic techniques, including 1H and 13C NMR, NOESY, HMQC, and HMBC. The absolute stereochemistry of these compounds was assigned on the basis of single-crystal X-ray crystallographic analysis of salvinicin A (4) and a 3,4-dichlorobenzoate derivative of salvinorin B.
Angelo A Izzo - One of the best experts on this subject based on the ideXlab platform.
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The hallucinogenic herb Salvia Divinorum and its active ingredient salvinorin A reduce inflammation‐induced hypermotility in mice
Neurogastroenterology and Motility, 2007Co-Authors: Raffaele Capasso, L Kutrzeba, Francesco Capasso, Giovanni Sarnelli, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Angelo A IzzoAbstract:The hallucinogenic plant Salvia Divinorum has been used for medical treatments of gastrointestinal disorders. Here, we evaluated the effect of a standardized extract from the leaves of Salvia Divinorum (SDE) and of its active ingredient salvinorin A on motility in vivo, both in physiological states and during croton oil-induced intestinal inflammation. SDE (1-100 mg kg(-1)) significantly inhibited motility only in inflamed, but not in control, mice. In control mice, salvinorin A (0.01-10 mg kg(-1)) significantly inhibited motility only at the highest doses tested (3 and 10 mg kg(-1)) and this effect was not counteracted by naloxone or by the kappa-opioid receptor (KOR) antagonist nor-binaltorphimine. Inflammation significantly increased the potency of salvinorin A (but not of the KOR agonist U-50488) in reducing motility. The inhibitory effects of both salvinorin A and U-50488 in inflamed mice were counteracted by naloxone or by nor-binaltorphimine. We conclude that salvinorin A may reduce motility through activation of different targets. In physiological states, salvinorin A, at high doses, inhibited motility through a non-KOR mediated mechanism. Gut inflammation increased the potency of salvinorin A; this effect was mediated by KOR, but it was not shared by U-50488, thus suggesting that salvinorin A may have target(s) other than KOR in the inflamed gut.
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the hallucinogenic herb Salvia Divinorum and its active ingredient salvinorin a reduce inflammation induced hypermotility in mice
Neurogastroenterology and Motility, 2007Co-Authors: Raffaele Capasso, L Kutrzeba, Francesco Capasso, Giovanni Sarnelli, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Angelo A IzzoAbstract:The hallucinogenic plant Salvia Divinorum has been used for medical treatments of gastrointestinal disorders. Here, we evaluated the effect of a standardized extract from the leaves of Salvia Divinorum (SDE) and of its active ingredient salvinorin A on motility in vivo, both in physiological states and during croton oil-induced intestinal inflammation. SDE (1-100 mg kg(-1)) significantly inhibited motility only in inflamed, but not in control, mice. In control mice, salvinorin A (0.01-10 mg kg(-1)) significantly inhibited motility only at the highest doses tested (3 and 10 mg kg(-1)) and this effect was not counteracted by naloxone or by the kappa-opioid receptor (KOR) antagonist nor-binaltorphimine. Inflammation significantly increased the potency of salvinorin A (but not of the KOR agonist U-50488) in reducing motility. The inhibitory effects of both salvinorin A and U-50488 in inflamed mice were counteracted by naloxone or by nor-binaltorphimine. We conclude that salvinorin A may reduce motility through activation of different targets. In physiological states, salvinorin A, at high doses, inhibited motility through a non-KOR mediated mechanism. Gut inflammation increased the potency of salvinorin A; this effect was mediated by KOR, but it was not shared by U-50488, thus suggesting that salvinorin A may have target(s) other than KOR in the inflamed gut.
Francesco Capasso - One of the best experts on this subject based on the ideXlab platform.
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inhibitory effect of salvinorin a from Salvia Divinorum on ileitis induced hypermotility cross talk between κ opioid and cannabinoid cb1 receptors
British Journal of Pharmacology, 2009Co-Authors: Roberta Capasso, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Maria Grazia Cascio, K Huben, P Marini, Barbara Romano, V. Di Marzo, Francesco CapassoAbstract:Background and purpose: Salvinorin A, the active component of the hallucinogenic herb Salvia Divinorum, inhibits intestinal motility through activation of κ-opioid receptors (KORs). However, this compound may have target(s) other than the KORs in the inflamed gut. Because intestinal inflammation upregulates cannabinoid receptors and endogenous cannabinoids, in the present study we investigated the possible involvement of the endogenous cannabinoid system in salvinorin A-induced delay in motility in the inflamed gut.
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Inhibitory effect of salvinorin A, from Salvia Divinorum, on ileitis‐induced hypermotility: cross‐talk between κ‐opioid and cannabinoid CB1 receptors
British journal of pharmacology, 2008Co-Authors: Roberta Capasso, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Maria Grazia Cascio, K Huben, P Marini, Barbara Romano, V. Di Marzo, Francesco CapassoAbstract:Background and purpose: Salvinorin A, the active component of the hallucinogenic herb Salvia Divinorum, inhibits intestinal motility through activation of κ-opioid receptors (KORs). However, this compound may have target(s) other than the KORs in the inflamed gut. Because intestinal inflammation upregulates cannabinoid receptors and endogenous cannabinoids, in the present study we investigated the possible involvement of the endogenous cannabinoid system in salvinorin A-induced delay in motility in the inflamed gut.
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The hallucinogenic herb Salvia Divinorum and its active ingredient salvinorin A reduce inflammation‐induced hypermotility in mice
Neurogastroenterology and Motility, 2007Co-Authors: Raffaele Capasso, L Kutrzeba, Francesco Capasso, Giovanni Sarnelli, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Angelo A IzzoAbstract:The hallucinogenic plant Salvia Divinorum has been used for medical treatments of gastrointestinal disorders. Here, we evaluated the effect of a standardized extract from the leaves of Salvia Divinorum (SDE) and of its active ingredient salvinorin A on motility in vivo, both in physiological states and during croton oil-induced intestinal inflammation. SDE (1-100 mg kg(-1)) significantly inhibited motility only in inflamed, but not in control, mice. In control mice, salvinorin A (0.01-10 mg kg(-1)) significantly inhibited motility only at the highest doses tested (3 and 10 mg kg(-1)) and this effect was not counteracted by naloxone or by the kappa-opioid receptor (KOR) antagonist nor-binaltorphimine. Inflammation significantly increased the potency of salvinorin A (but not of the KOR agonist U-50488) in reducing motility. The inhibitory effects of both salvinorin A and U-50488 in inflamed mice were counteracted by naloxone or by nor-binaltorphimine. We conclude that salvinorin A may reduce motility through activation of different targets. In physiological states, salvinorin A, at high doses, inhibited motility through a non-KOR mediated mechanism. Gut inflammation increased the potency of salvinorin A; this effect was mediated by KOR, but it was not shared by U-50488, thus suggesting that salvinorin A may have target(s) other than KOR in the inflamed gut.
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the hallucinogenic herb Salvia Divinorum and its active ingredient salvinorin a reduce inflammation induced hypermotility in mice
Neurogastroenterology and Motility, 2007Co-Authors: Raffaele Capasso, L Kutrzeba, Francesco Capasso, Giovanni Sarnelli, Gabriella Aviello, Francesca Borrelli, Jordan K. Zjawiony, Angelo A IzzoAbstract:The hallucinogenic plant Salvia Divinorum has been used for medical treatments of gastrointestinal disorders. Here, we evaluated the effect of a standardized extract from the leaves of Salvia Divinorum (SDE) and of its active ingredient salvinorin A on motility in vivo, both in physiological states and during croton oil-induced intestinal inflammation. SDE (1-100 mg kg(-1)) significantly inhibited motility only in inflamed, but not in control, mice. In control mice, salvinorin A (0.01-10 mg kg(-1)) significantly inhibited motility only at the highest doses tested (3 and 10 mg kg(-1)) and this effect was not counteracted by naloxone or by the kappa-opioid receptor (KOR) antagonist nor-binaltorphimine. Inflammation significantly increased the potency of salvinorin A (but not of the KOR agonist U-50488) in reducing motility. The inhibitory effects of both salvinorin A and U-50488 in inflamed mice were counteracted by naloxone or by nor-binaltorphimine. We conclude that salvinorin A may reduce motility through activation of different targets. In physiological states, salvinorin A, at high doses, inhibited motility through a non-KOR mediated mechanism. Gut inflammation increased the potency of salvinorin A; this effect was mediated by KOR, but it was not shared by U-50488, thus suggesting that salvinorin A may have target(s) other than KOR in the inflamed gut.
