Salvinorin B metoksimetil etar

Salvinorin B metoksimetil etar
(IUPAC) ime
	(2S,4aR,6aR,7R,9S,10aS,10bR)- 9-(methoxymethoxy)- 2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho-[2,1-c]pyran-7-carboxylic acid methyl ester
Klinički podaci
Identifikatori
ATC kod	nije dodeljen
PubChem	11407876
ChemSpider	23323947
ChEMBL	CHEMBL258098
Hemijski podaci
Formula	C23H30O8
Mol. masa	434 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C23H30O8/c1-22-7-5-14-21(26)31-17(13-6-8-29-11-13)10-23(14,2)19(22)18(24)16(30-12-27-3)9-15(22)20(25)28-4/h6,8,11,14-17,19H,5,7,9-10,12H2,1-4H3/t14-,15-,16-,17-,19-,22-,23-/m0/s1 ; Key: KFVUSZPWUZBAPF-AGQYDFLVSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Legalan

Salvinorin B metoksimetil etar (2-Metoksimetil salvinorin B) je semi-sintetički analog prirodnog proizvoda salvinorina A. Ovo jedinjenje koristi se u naučnim istraživanjima.^[5]^[6] On ima duže trajanje od oko 2–3 sata, u poređenju sa manje od 30 minuta salvinorina A,^[7] i povišeni afinitet i efikasnost za κ-opioidni receptor. Poput srodnog jedinjenja herkinorina, 2-metoksimetil salvinorin B se pravi od salvinorina B, koji nastaje deacetilacijom salvinorina A.^[8] Dok su oba jedinjenja, salvinorin A i salvinorin B, nađena u biljci Salvia divinorum, salvinorin A je prisutan u većim količinama.^[9]

Salvinorin B metoksimetil etar ima Ki od 0.60 nM na κ opioidnom receptoru,^[10] i oko 5x je potentniji od salvinorina A u životinjskim studijama, mada je još uvek upola manje potentatan nego jači homolog 2-etoksimetil salvinorin B.^[11]

Vidi još uredi

Literatura uredi

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Inan S, Lee DY, Liu-Chen LY, Cowan A (March 2009). „Comparison of the diuretic effects of chemically diverse kappa opioid agonists in rats: nalfurafine, U50,488H, and salvinorin A”. Naunyn-Schmiedeberg's Archives of Pharmacology 379 (3): 263–70. DOI:10.1007/s00210-008-0358-8. PMID 18925386.
↑ McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, Mohabbat Y, Moyer RA, Bohn LM, Coscia CJ (December 2008). „Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways”. Journal of Neurochemistry 107 (6): 1753–65. DOI:10.1111/j.1471-4159.2008.05745.x. PMC 2606093. PMID 19014370.
↑ Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, Cowan A, Liu-Chen LY (March 2008). „2-Methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A”. The Journal of Pharmacology and Experimental Therapeutics 324 (3): 1073–83. DOI:10.1124/jpet.107.132142. PMC 2519046. PMID 18089845.
↑ Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B (August 2005). „Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues”. Bioorganic & Medicinal Chemistry Letters 15 (16): 3744–7. DOI:10.1016/j.bmcl.2005.05.048. PMID 15993589.
↑ Medana C, Massolino C, Pazzi M, Baiocchi C (2006). „Determination of salvinorins and divinatorins in Salvia divinorum leaves by liquid chromatography/multistage mass spectrometry”. Rapid Communications in Mass Spectrometry : RCM 20 (2): 131–6. DOI:10.1002/rcm.2288. PMID 16331747.
↑ Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, Cohen BM, Béguin C (February 2008). „Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers”. Bioorganic & Medicinal Chemistry 16 (3): 1279–86. DOI:10.1016/j.bmc.2007.10.067. PMC 2568987. PMID 17981041.
↑ Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL (April 2009). „Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats”. Psychopharmacology 203 (2): 203–11. DOI:10.1007/s00213-008-1458-3. PMID 19153716.

Spoljašnje veze uredi

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	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid18925386-5] Inan S, Lee DY, Liu-Chen LY, Cowan A (March 2009). „Comparison of the diuretic effects of chemically diverse kappa opioid agonists in rats: nalfurafine, U50,488H, and salvinorin A”. Naunyn-Schmiedeberg's Archives of Pharmacology 379 (3): 263–70. DOI:10.1007/s00210-008-0358-8. PMID 18925386.

[pmid19014370-6] McLennan GP, Kiss A, Miyatake M, Belcheva MM, Chambers KT, Pozek JJ, Mohabbat Y, Moyer RA, Bohn LM, Coscia CJ (December 2008). „Kappa opioids promote the proliferation of astrocytes via Gbetagamma and beta-arrestin 2-dependent MAPK-mediated pathways”. Journal of Neurochemistry 107 (6): 1753–65. DOI:10.1111/j.1471-4159.2008.05745.x. PMC 2606093. PMID 19014370.

[pmid18089845-7] Wang Y, Chen Y, Xu W, Lee DY, Ma Z, Rawls SM, Cowan A, Liu-Chen LY (March 2008). „2-Methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A”. The Journal of Pharmacology and Experimental Therapeutics 324 (3): 1073–83. DOI:10.1124/jpet.107.132142. PMC 2519046. PMID 18089845.

[pmid15993589-8] Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B (August 2005). „Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues”. Bioorganic & Medicinal Chemistry Letters 15 (16): 3744–7. DOI:10.1016/j.bmcl.2005.05.048. PMID 15993589.

[pmid16331747-9] Medana C, Massolino C, Pazzi M, Baiocchi C (2006). „Determination of salvinorins and divinatorins in Salvia divinorum leaves by liquid chromatography/multistage mass spectrometry”. Rapid Communications in Mass Spectrometry : RCM 20 (2): 131–6. DOI:10.1002/rcm.2288. PMID 16331747.

[pmid17981041-10] Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, Cohen BM, Béguin C (February 2008). „Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers”. Bioorganic & Medicinal Chemistry 16 (3): 1279–86. DOI:10.1016/j.bmc.2007.10.067. PMC 2568987. PMID 17981041.

[pmid19153716-11] Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, Walker SL (April 2009). „Comparison of the discriminative stimulus effects of salvinorin A and its derivatives to U69,593 and U50,488 in rats”. Psychopharmacology 203 (2): 203–11. DOI:10.1007/s00213-008-1458-3. PMID 19153716.

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