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Salvinorin B ethoxymethyl ether

FieldValue
verifiedrevid414178678
image2-EtOMeSalB.png
image_classskin-invert-image
width250px
legal_statusLegal/Uncontrolled
classκ-Opioid receptor agonist; Hallucinogen
ATC_prefixNone
PubChem24873526
ChemSpiderID_Ref
ChemSpiderID23323659
ChEMBL_Ref
ChEMBL272939
synonyms2-*O*-Ethoxymethylsalvinorin B; 2-EMSB; Symmetry
IUPAC_name(2*S*,4a*R*,6a*R*,7*R*,9*S*,10a*S*,10b*R*)-9-(ethoxymethoxy)-2-(3-furanyl)dodecahydro -6a,10b-dimethyl-4,10-dioxo-2*H*-naphtho-[2,1-c]pyran-7-carboxylic acid methyl ester
C24H=32O=8
SMILESCCOCO[C@H]1C[C@H]([C@@]2(CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]2C1=O)C)C4=COC=C4)C)C(=O)OC
StdInChI_Ref
StdInChI1S/C24H32O8/c1-5-29-13-31-17-10-16(21(26)28-4)23(2)8-6-15-22(27)32-18(14-7-9-30-12-14)11-24(15,3)20(23)19(17)25/h7,9,12,15-18,20H,5-6,8,10-11,13H2,1-4H3/t15-,16-,17-,18-,20-,23-,24-/m0/s1
StdInChIKey_Ref
StdInChIKeyICVTXAUKIHJDGV-WFOQEEKOSA-N

Salvinorin B ethoxymethyl ether, also known as 2-O-ethoxymethylsalvinorin B (2-EMSB) or as symmetry, is a semi-synthetic analogue of the natural product salvinorin A, with a longer duration of action of around 3hours (compared to less than 30minutes for salvinorin A), and increased affinity and intrinsic activity at the κ-opioid receptor. Like the related compound herkinorin, 2-EMSB is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation, as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.

2-EMSB has an affinity (Ki) of 0.32nM at the κ-opioid receptor, and around 3,000 times selectivity over the μ- and δ-opioid receptors, making it one of the most potent and selective κ-opioid receptor agonists yet discovered. In animal studies it fully substituted for salvinorin A and the synthetic κ-opioid receptor agonist U-69593, and was active at doses as low as 0.005mg/kg. Human bioassays found the compound to be active at 50 μg smoked.

It has been sold online as an analytical standard.

References

References

  1. "2-О-Этоксиметилсальвинорин B (Salvinorin B ethoxymethyl ether)".
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. [http://www.erowid.org/chemicals/salvinorin_b_ethoxymethyl_ether/salvinorin_b_ethoxymethyl_ether_article1.shtml First Look at a New Psychoactive Drug:Symmetry (salvinorin B ethoxymethyl ether). ''The Entheogen Review''. 2008;16(4):136-45.]
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designer-drugs ethers ethoxy-compounds furans hallucinogenic-kappa-opioid-receptor-agonists lactones methyl-esters naphthopyrans semisynthetic-opioids
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