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| Other names | 2-O-Ethoxymethylsalvinorin B; 2-EMSB; Symmetry |
| Drug class | κ-Opioid receptor agonist; Hallucinogen |
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| Formula | C24H32O8 |
| Molar mass | 448.512 g·mol−1 |
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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, the psychoactive chemical in Salvia Divinorum, with a longer duration of action of around 3 hours (compared to less than 30 minutes for salvinorin A), and increased affinity and intrinsic activity at the κ-opioid receptor.[1] Like the related compound herkinorin, 2-EMSB is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation,[2] as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum, salvinorin A is present in larger quantities.[3]
2-EMSB has an affinity (Ki) of 0.32 nM 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.[4] 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 0.005 mg/kg.[5] Human bioassays found the compound to be active at 50 μg smoked.[6][1]
It has been sold online as an analytical standard.[1]
See also
[edit]- κ-Opioid receptor agonist
- Salvinorin B
- 2-Methoxymethyl salvinorin B (2-MMSB)
- Herkinorin
- RB-64 (22-thiocyanatosalvinorin A)
- Salvinorin A
References
[edit]- 1 2 3 "2-О-Этоксиметилсальвинорин B (Salvinorin B ethoxymethyl ether)". АИПСИН (in Russian). Retrieved 1 January 2026.
- ↑ Lee DY, Karnati VV, He M, Liu-Chen LY, Kondaveti L, Ma Z, et al. (August 2005). "Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues". Bioorganic & Medicinal Chemistry Letters. 15 (16): 3744–3747. 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. 20 (2): 131–136. doi:10.1002/rcm.2288. PMID 16331747.
- ↑ Munro TA, Duncan KK, Xu W, Wang Y, Liu-Chen LY, Carlezon WA, et al. (February 2008). "Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers". Bioorganic & Medicinal Chemistry. 16 (3): 1279–1286. doi:10.1016/j.bmc.2007.10.067. PMC 2568987. PMID 17981041.
- ↑ Baker LE, Panos JJ, Killinger BA, Peet MM, Bell LM, Haliw LA, et al. (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): 203–211. doi:10.1007/s00213-008-1458-3. PMID 19153716.
- ↑ Mercury D, Feelodd D (2008). "First Look at a New Psychoactive Drug: Symmetry (Salvinorin B Ethoxymethyl Ether)". The Entheogen Review. 16 (4): 136–145. ISSN 1066-1913.