Salvinorin A | CAS#83729-01-5 | κ opioid selective receptor agonist

MedKoo Cat#: 330174 | Name: Salvinorin A

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Salvinorin A is a potent, non-nitrogenous κ opioid selective receptor agonist. Salvinorin A is isolated from Salvia divinorum. Salvinorin A preserves cerebral pial artery autoregulation after forebrain ischemia via the PI3K/AKT/cGMP pathway. Salvinorin A ameliorates cerebral vasospasm through activation of endothelial nitric oxide synthase in a rat model of subarachnoid hemorrhage.

Chemical Structure

Salvinorin A

CAS#83729-01-5

Theoretical Analysis

MedKoo Cat#: 330174

Name: Salvinorin A

CAS#: 83729-01-5

Chemical Formula: C23H28O8

Exact Mass: 432.1784

Molecular Weight: 432.47

Elemental Analysis: C, 63.88; H, 6.53; O, 29.60

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 400.00	2 weeks
5mg	USD 1,050.00	2 Weeks

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Related CAS #

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Synonym

Salvinorin A; Salvinorin-A;

IUPAC/Chemical Name

methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetoxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxododecahydro-2H-benzo[f]isochromene-7-carboxylate

InChi Key

OBSYBRPAKCASQB-AGQYDFLVSA-N

InChi Code

InChI=1S/C23H28O8/c1-12(24)30-16-9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(22)18(16)25/h6,8,11,14-17,19H,5,7,9-10H2,1-4H3/t14-,15-,16-,17-,19-,22-,23-/m0/s1

SMILES Code

O=C([C@H](C[C@H](OC(C)=O)C([C@@]12[H])=O)[C@]1(C)CC[C@@]([C@]2(C)C[C@@H](C3=COC=C3)O4)([H])C4=O)OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and acetonitrile

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Salvinorin A is a non-nitrogenous κ-opioid selective agonist that displays high affinity at both native (Ki = 4.3 nM) and cloned (Ki = 16 nM) κ-opioid receptors. Salvinorin A exhibits allosteric modulation of μ-opioid receptor binding.

In vitro activity:

Salvinorin A showed promising in vitro activity against allergic rhinitis. Salvinorin A inhibited histamine and β-hexosaminidase release, as well as the production of inflammatory cytokines (such as interleukin-4 and tumor necrosis factor-α) in rat basophilic leukemia cells. Salvinorin A dampened granule release and F-actin organization in these cells. Reference: FEBS Open Bio. 2021 Aug;11(8):2166-2173. https://pubmed.ncbi.nlm.nih.gov/34092045/

In vivo activity:

Salvinorin A may be a potential treatment for ischemic stroke. Intranasal Salvinorin A administration after ischemic stroke in adult male mice with transient Middle Cerebral Artery Occlusion reduced brain inflammation, shifted microglia/macrophages to a less inflammatory state, and reduced immune cell infiltration into the brain. Salvinorin A also protected the blood-brain barrier, reduced long-term brain damage, and improved neurological function in mice. Reference: J Neuroimmune Pharmacol. 2022 Jun;17(1-2):350-366. https://pubmed.ncbi.nlm.nih.gov/34596819/

	Solvent	mg/mL	mM
Solubility
	Acetonitrile	1.0	2.31
	DMF	1.0	2.31
	DMSO	2.0	4.62

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 432.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Shou Q, Tan T, Xu F. Salvinorin A inhibits ovalbumin-stimulated allergic rhinitis and RBL-2H3 cells degranulation. FEBS Open Bio. 2021 Aug;11(8):2166-2173. doi: 10.1002/2211-5463.13219. Epub 2021 Jun 25. PMID: 34092045; PMCID: PMC8329952. 2. Martinho A, Silva SM, Gallardo E. Cytotoxic Effects of Salvinorin A, A Major Constituent of Salvia divinorum. Med Chem. 2016;12(5):432-40. doi: 10.2174/1573406411666151005105617. PMID: 26434801. 3. Misilimu D, Li W, Chen D, Wei P, Huang Y, Li S, Grothusen J, Gao Y. Intranasal Salvinorin A Improves Long-term Neurological Function via Immunomodulation in a Mouse Ischemic Stroke Model. J Neuroimmune Pharmacol. 2022 Jun;17(1-2):350-366. doi: 10.1007/s11481-021-10025-4. Epub 2021 Oct 1. PMID: 34596819; PMCID: PMC9726789. 4. Zeng S, Chen D, Liu G, Wu YX, Gao ZQ, Su Y, Yuan JN, Liu L, Shan JC, Pang QF, Zhu T. Salvinorin A protects against methicillin resistant staphylococcus aureus-induced acute lung injury via Nrf2 pathway. Int Immunopharmacol. 2021 Jan;90:107221. doi: 10.1016/j.intimp.2020.107221. Epub 2020 Dec 3. PMID: 33293260.

In vitro protocol:

In vivo protocol:

1. Misilimu D, Li W, Chen D, Wei P, Huang Y, Li S, Grothusen J, Gao Y. Intranasal Salvinorin A Improves Long-term Neurological Function via Immunomodulation in a Mouse Ischemic Stroke Model. J Neuroimmune Pharmacol. 2022 Jun;17(1-2):350-366. doi: 10.1007/s11481-021-10025-4. Epub 2021 Oct 1. PMID: 34596819; PMCID: PMC9726789. 2. Zeng S, Chen D, Liu G, Wu YX, Gao ZQ, Su Y, Yuan JN, Liu L, Shan JC, Pang QF, Zhu T. Salvinorin A protects against methicillin resistant staphylococcus aureus-induced acute lung injury via Nrf2 pathway. Int Immunopharmacol. 2021 Jan;90:107221. doi: 10.1016/j.intimp.2020.107221. Epub 2020 Dec 3. PMID: 33293260.

1: Kivell BM, Paton KF, Kumar N, Morani AS, Culverhouse A, Shepherd A, Welsh SA, Biggerstaff A, Crowley RS, Prisinzano TE. Kappa Opioid Receptor Agonist Mesyl Sal B Attenuates Behavioral Sensitization to Cocaine with Fewer Aversive Side-Effects than Salvinorin A in Rodents. Molecules. 2018 Oct 11;23(10). pii: E2602. doi: 10.3390/molecules23102602. PubMed PMID: 30314288; PubMed Central PMCID: PMC6222496. 2: Wang Y, Metz P. Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels-Alder Strategy. Org Lett. 2018 Jun 1;20(11):3418-3421. doi: 10.1021/acs.orglett.8b01357. Epub 2018 May 22. PubMed PMID: 29787286. 3: Dong HP, Zhou W, Ma XX, He ZZ, Wang ZH. Salvinorin A preserves cerebral pial artery autoregulation after forebrain ischemia via the PI3K/AKT/cGMP pathway. Braz J Med Biol Res. 2018 Mar 15;51(5):e6714. doi: 10.1590/1414-431X20176714. PubMed PMID: 29561955; PubMed Central PMCID: PMC5875901. 4: Hirasawa S, Cho M, Brust TF, Roach JJ, Bohn LM, Shenvi RA. O6C-20-nor-salvinorin A is a stable and potent KOR agonist. Bioorg Med Chem Lett. 2018 Sep 1;28(16):2770-2772. doi: 10.1016/j.bmcl.2018.01.055. Epub 2018 Jan 31. PubMed PMID: 29426768; PubMed Central PMCID: PMC6067998. 5: Sun J, Zhang Y, Lu J, Zhang W, Yan J, Yang L, Zhou C, Liu R, Chen C. Salvinorin A ameliorates cerebral vasospasm through activation of endothelial nitric oxide synthase in a rat model of subarachnoid hemorrhage. Microcirculation. 2018 Apr;25(3):e12442. doi: 10.1111/micc.12442. PubMed PMID: 29377443. 6: Roach JJ, Sasano Y, Schmid CL, Zaidi S, Katritch V, Stevens RC, Bohn LM, Shenvi RA. Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist. ACS Cent Sci. 2017 Dec 27;3(12):1329-1336. doi: 10.1021/acscentsci.7b00488. Epub 2017 Dec 13. PubMed PMID: 29296674; PubMed Central PMCID: PMC5746855. 7: Coffeen U, Canseco-Alba A, Simón-Arceo K, Almanza A, Mercado F, León-Olea M, Pellicer F. Salvinorin A reduces neuropathic nociception in the insular cortex of the rat. Eur J Pain. 2018 Feb;22(2):311-318. doi: 10.1002/ejp.1120. Epub 2017 Oct 4. PubMed PMID: 28975684. 8: Ewald AWM, Bosch PJ, Culverhouse A, Crowley RS, Neuenswander B, Prisinzano TE, Kivell BM. The C-2 derivatives of salvinorin A, ethoxymethyl ether Sal B and β-tetrahydropyran Sal B, have anti-cocaine properties with minimal side effects. Psychopharmacology (Berl). 2017 Aug;234(16):2499-2514. doi: 10.1007/s00213-017-4637-2. Epub 2017 May 23. PubMed PMID: 28536865; PubMed Central PMCID: PMC5542847. 9: Paudel MK, Shirota O, Sakamoto S, Morimoto S, Tanaka H. An immunochromatographic assay for rapid etection of salvinorin A. J Immunoassay Immunochem. 2017;38(4):438-448. doi: 10.1080/15321819.2017.1324797. Epub 2017 May 5. PubMed PMID: 28475466. 10: Sherwood AM, Crowley RS, Paton KF, Biggerstaff A, Neuenswander B, Day VW, Kivell BM, Prisinzano TE. Addressing Structural Flexibility at the A-Ring on Salvinorin A: Discovery of a Potent Kappa-Opioid Agonist with Enhanced Metabolic Stability. J Med Chem. 2017 May 11;60(9):3866-3878. doi: 10.1021/acs.jmedchem.7b00148. Epub 2017 Apr 19. PubMed PMID: 28376298; PubMed Central PMCID: PMC5546011. 11: Chen X, Berim A, Dayan FE, Gang DR. A (-)-kolavenyl diphosphate synthase catalyzes the first step of salvinorin A biosynthesis in Salvia divinorum. J Exp Bot. 2017 Feb 1;68(5):1109-1122. doi: 10.1093/jxb/erw493. PubMed PMID: 28204567; PubMed Central PMCID: PMC5441855. 12: Cruz A, Domingos S, Gallardo E, Martinho A. A unique natural selective kappa-opioid receptor agonist, salvinorin A, and its roles in human therapeutics. Phytochemistry. 2017 May;137:9-14. doi: 10.1016/j.phytochem.2017.02.001. Epub 2017 Feb 10. PubMed PMID: 28190678. 13: Paton KF, Kumar N, Crowley RS, Harper JL, Prisinzano TE, Kivell BM. The analgesic and anti-inflammatory effects of Salvinorin A analogue β-tetrahydropyran Salvinorin B in mice. Eur J Pain. 2017 Jul;21(6):1039-1050. doi: 10.1002/ejp.1002. Epub 2017 Feb 3. PubMed PMID: 28158929; PubMed Central PMCID: PMC5466480. 14: Rossi A, Caiazzo E, Bilancia R, Riemma MA, Pagano E, Cicala C, Ialenti A, Zjawiony JK, Izzo AA, Capasso R, Roviezzo F. Salvinorin A Inhibits Airway Hyperreactivity Induced by Ovalbumin Sensitization. Front Pharmacol. 2017 Jan 13;7:525. doi: 10.3389/fphar.2016.00525. eCollection 2016. PubMed PMID: 28133450; PubMed Central PMCID: PMC5233683. 15: Pelot KA, Mitchell R, Kwon M, Hagelthorn DM, Wardman JF, Chiang A, Bohlmann J, Ro DK, Zerbe P. Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of the Salvia divinorum clerodienyl diphosphate synthase. Plant J. 2017 Mar;89(5):885-897. doi: 10.1111/tpj.13427. Epub 2017 Feb 6. PubMed PMID: 27865008. 16: Xu X, Ma S, Feng Z, Hu G, Wang L, Xie XQ. Chemogenomics knowledgebase and systems pharmacology for hallucinogen target identification-Salvinorin A as a case study. J Mol Graph Model. 2016 Nov;70:284-295. doi: 10.1016/j.jmgm.2016.08.001. Epub 2016 Aug 8. PubMed PMID: 27810775; PubMed Central PMCID: PMC5327504. 17: Line NJ, Burns AC, Butler SC, Casbohm J, Forsyth CJ. Total Synthesis of (-)-Salvinorin A. Chemistry. 2016 Dec 12;22(50):17983-17986. doi: 10.1002/chem.201604853. Epub 2016 Nov 4. PubMed PMID: 27758012. 18: Xin J, Zhang Y, He Z, Wang Z. Highly selective non-opioid kappa opioid receptor (KOR) agonist salvinorin A protects against forebrain ischemia-induced brain injury in rats. Brain Res. 2016 Apr 15;1637:168-176. doi: 10.1016/j.brainres.2016.02.024. Epub 2016 Feb 21. PubMed PMID: 26907190. 19: Taylor GT, Manzella F. Kappa Opioids, Salvinorin A and Major Depressive Disorder. Curr Neuropharmacol. 2016;14(2):165-76. Review. PubMed PMID: 26903446; PubMed Central PMCID: PMC4825947. 20: Johnson MW, MacLean KA, Caspers MJ, Prisinzano TE, Griffiths RR. Time course of pharmacokinetic and hormonal effects of inhaled high-dose salvinorin A in humans. J Psychopharmacol. 2016 Apr;30(4):323-9. doi: 10.1177/0269881116629125. Epub 2016 Feb 15. PubMed PMID: 26880225; PubMed Central PMCID: PMC5289219.