92545-30-7Relevant articles and documents
Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists
Lee, David Y.W.,Deng, Gang,Ma, Zhongze,Xu, Wei,Yang, Lu,Liu, Jing,Dai, Ronghua,Liu-Chen, Lee-Yuan
, p. 4689 - 4692 (2015)
The synthesis of a new series of C-2-alkyl-2-methoxymethyl-salvinorin ethers and their binding affinities at κ-, μ-, and δ-opioid receptors are presented. We have developed a synthesis that enables installation of alkyl-substituents at C-2 while maintaining the integrity of the C-2 methoxymethyl ether and retaining κ-opioid receptor binding activity. Among these new compounds, 2-methyl-2-methoxymethyl-salvinorin ether (9a) is a potent full agonist at the κ receptor and shows comparable potency in Ki and EC50 with salvinorin A and U50488H. These C2-alkylated analogs have been identified as full κ agonists.
A facile method for the preparation of deuterium labeled salvinorin A: Synthesis of [2,2,2-2H3]-salvinorin a
Tidgewell, Kevin,Harding, Wayne W.,Schmidt, Mark,Holden, Kenneth G.,Murry, Daryl J.,E. Prisinzano, Thomas
, p. 5099 - 5102 (2004)
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.
Salvinorin immunoassay
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Page/Page column 8, (2016/02/03)
The present invention provides an immunoassay method for detecting or determining the amount of salvinorin A, salvinorin B and/or analogues thereof in an in vitro sample, an antibody for salvinorin A, salvinorin B and/or analogues thereof and a kit for detecting the presence of or determining the amount of salvinorin A, salvinorin B and its analogues thereof in a sample.
Development of an enzyme immunoassay using a monoclonal antibody against the psychoactive diterpenoid salvinorin A
Paudel, Madan Kumar,Shirota, Osamu,Sasaki-Tabata, Kaori,Tanaka, Hiroyuki,Sekita, Setsuko,Morimoto, Satoshi
, p. 1654 - 1660 (2013/10/22)
Salvinorin A (1), the main active constituent in Salvia divinorum, is a highly selective kappa-opioid receptor agonist with hallucinogenic effects, which is regulated in several countries. In the present study, a monoclonal antibody (mAb) against 1 was prepared, and an indirect competitive enzyme-linked immunosorbent assay (icELISA) system was developed for the detection of salvinorins. To raise mAbs against 1, salvinorin B (2) hemisuccinate was synthesized and used to prepare the immunogen 2-bovine serum albumin conjugate. This technique was used to prepare a hybridoma cell line, 3D5, which secreted a mAb that recognized 1. The mAb was shown to have specificity for 1 and other salvinorins in cross-reactivity tests. The intra-assay calibration range by icELISA using the mAb against 1 was 0.0195-0.625 μg/mL. After validating the icELISA using intra- and interassays, a recovery experiment and analysis of several plants in the family Lamiaceae, including S. divinorum, confirmed that the analytical method based on ELISA is not only simple but also precise, accurate, sensitive, and sufficiently reliable. The results indicate that icELISA is a useful tool in the identification of S. divinorum.
Asymmetric synthesis of salvinorin A, a potent κ opioid receptor agonist
Scheerer, Jonathan R.,Lawrence, Jonathan F.,Wang, Grace C.,Evans, David A.
, p. 8968 - 8969 (2008/02/12)
The stereoselective synthesis of salvinorin A is described. A macrocyclic bis-Michael reaction cascade provides the requisite tricyclic skeleton as a single diastereomer. Copyright
Opioid receptor ligands and methods for their preparation
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Page/Page column 11; Figure 2, (2008/06/13)
The invention provides novel compounds of formula I: that are opioid receptor ligands. The invention also provides pharmaceutical compositions comprising such compounds as well as methods for treating diseases associated with opioid receptor function by a
AGENTS WITH SELECTIVE K-OPIOID RECEPTOR AFFINITY
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Page/Page column 16-17, (2008/06/13)
Compounds and compositions that are salvinorin A and salvinorin B derivatives that demonstrate selectivity and/or potency for the k-opioid receptor (KOR), allowing for their use as medicines, as well as chemical probes (both radiolabeled and cold) for fields utilizing the techniques of radiolabeled binding assays.
Bioisosteric modification of salvinorin A, a potent and selective kappa-opioid receptor agonist
Stewart, D. Jeremy,Fahmy, Hesham,Roth, Bryan L.,Yan, Feng,Zjawiony, Jordan K.
, p. 269 - 275 (2007/10/03)
Salvinorin A ((2S,4aR,6aR,7R,9S,10aS, 10bR)-2H-naphtho[2,1-c]pyran-7- carboxylic acid, 9-(acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10- dioxo methyl ester, 1, CAS 83729-01-5) has been shown to bind with high affinity and selectivity to the kappa-opioid receptor (KOR) as an agonist. Bioisosteres of 1 were developed and biologically evaluated in binding and functional assays. The C-2 thioacetate isoster produced comparable activity to 1, but nitrogen substitution had a diminishing effect. Intermediates, which lack a β-carbonyl at C-2, displayed moderate affinity. The derivatives were tested against all opioid subtypes and were selective towards KOR. ECV · Editio Cantor Verlag, Aulendort.
Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues
Lee, David Y.W.,Karnati, Vishnu V.R.,He, Minsheng,Liu-Chen, Lee-Yuan,Kondaveti, Leelakrishna,Ma, Zhongze,Wang, Yulin,Chen, Yong,Beguin, Cecile,Carlezon Jr., William A.,Cohen, Bruce
, p. 3744 - 3747 (2007/10/03)
Salvinorin A is the most potent naturally occurring opioid agonist yet discovered with high selectivity and affinity for κ-opioid receptor. To explore its structure and activity relationships, a series of salvinorin A derivatives modified at the C(2) position were prepared and studied. These salvinorin A derivatives were screened for binding and functional activities at the human κ-opioid receptor. Compound 4, containing a methoxymethyl group at the 2-position, was a full κ-agonist with an EC50 value at 0.6 nM, which is about 7 times more potent than salvinorin A.
Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)
Beguin, Cecile,Richards, Michele R.,Wang, Yulin,Chen, Yong,Liu-Chen, Lee-Yuan,Ma, Zhongze,Lee, David Y. W.,Carlezon Jr., William A.,Cohen, Bruce M.
, p. 2761 - 2765 (2007/10/03)
Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate 9 was a potent κ-agonist (EC50 = 6.2 nM) and should be more stable than salvinorin A toward metabolic transformations. Compound 10, containing an N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed.
