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2-Ethoxymethyl Salvinorin B
Systematic (IUPAC) name
(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(ethoxymethoxy)-2-(3-furanyl)dodecahydro -6a,10b-dimethyl-4,10-dioxo-2H-naphtho-[2,1-c]pyran-7-carboxylic acid methyl ester
Identifiers
CAS number  ?
ATC code none
PubChem 24873526
Chemical data
Formula C 24H32O8  
Mol. mass 448.505 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Legal
Routes  ?

2-Ethoxymethyl Salvinorin B (Symmetry, 2-EtOMe-Sal B) is a semi-synthetic analogue of the natural product Salvinorin A, with a longer duration of action of around 3 hours (compared to less than 30 minutes for Salvinorin A), and increased affinity and efficacy at the κ-opioid receptor. Like the related compound herkinorin, 2-Ethoxymethyl Salvinorin B is made from Salvinorin B, which is most conveniently made from Salvinorin A by deacetylation,[1] as while both Salvinorin A and Salvinorin B are found in the plant Salvia divinorum, Salvinorin A is present in larger quantities.[2]

2-Ethoxymethyl Salvinorin B has a Ki of 0.32nM at the κ opioid receptor, and around 3000x selectivity over the μ and δ opioid receptors, making it one of the most potent and selective kappa agonists yet discovered.[3] In animal studies it fully substituted for Salvinorin A and the synthetic kappa agonist U-69593, and was active at doses as low as 0.005 mg/kg.[4] Human bioassays found the compound to be active at 50μg, but generally unpleasant in effects.[5]

See also

References

  1. ^ 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.  
  2. ^ 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.  
  3. ^ 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. PMID 17981041.  
  4. ^ 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.  
  5. ^ First Look at a New Psychoactive Drug:Symmetry (salvinorin B ethoxymethyl ether). The Entheogen Review. 2008;16(4):136-45.







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