Salvinorin A

Base Information

• Chemical Name: Salvinorin A
• CAS No.: 83729-01-5
• Molecular Formula: C23H28 O8
• Molecular Weight: 432.47
• European Community (EC) Number: 689-027-2
• UNII: T56W91NG6J
• DSSTox Substance ID: DTXSID80232584
• Nikkaji Number: J1.805.239C
• Wikipedia: Salvinorin_A
• Wikidata: Q413512
• Pharos Ligand ID: LSBKN8K56HZF
• Metabolomics Workbench ID: 134293
• ChEMBL ID: CHEMBL445332
• Mol file: 83729-01-5.mol

Synonyms:(-)-salvinorin A;1-deoxo-1,10-dehydrosalvinorin A;12-epi-salvinorin A;divinorin A;salvinorin;salvinorin A

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Chemical Property of Salvinorin A

Chemical Property:

• Vapor Pressure: 9.8E-13mmHg at 25°C
• Melting Point: 238-240° (Ortega); mp 242-244° (Valdes, 1984)
• Boiling Point: 563.8°C at 760 mmHg
• Flash Point: 294.8°C
• PSA: 109.11000
• Density: 1.28g/cm³
• LogP: 3.00010
• Storage Temp.: −20°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 432.17841785
• Heavy Atom Count: 31
• Complexity: 792

Purity/Quality:

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 22-24/25-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC(=O)OC1CC(C2(CCC3C(=O)OC(CC3(C2C1=O)C)C4=COC=C4)C)C(=O)OC
• Isomeric SMILES: CC(=O)O[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
• Recent ClinicalTrials: Effects of Salvinorin A in Healthy Controls
• Description: Salvinorin A (Item No. 11487) is an analytical reference material categorized as a diterpene. It is a hallucinogen derived from S. divinorum that has been used in the traditional spiritual practices of the Mazatec Indians and as a recreational drug. This product is intended for research and forensic applications.
• Uses: Salvinorin A is a potent and selective kappa-opioid receptor agonist. Salvinorin A has been reported to be brain-penetrant and displays psychoactive properties; hallucinogen. Salvinorin A is a hallucinogenic derived from the S. divinorum plant used in traditional spiritual practices of the Mazatec Indians and now gaining popularity as a recreational drug. Unlike other hallucinogens, which mediate their effects through serotonin 5-HT2A receptors, salvinorin A is a potent, selective κ-opioid receptor agonist (Ki = 2.4 nM; EC50 = 1.8 nM). This product is intended for forensic and research applications.In traditional medicine, the leaves are used for divination and for treatment of anemia and excretory functions. In traditional medicine, the leaves are used for divination and for treatment of anemia and excretory functions.

Technology Process of Salvinorin A

There total 27 articles about Salvinorin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

C23H30O8 → salvinorin A (83729-01-5)

Guidance literature:

With magnesium sulfate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; Molecular sieve;

DOI:10.1002/chem.202100560

Reference yield: 86.0%

methyl (13S,1R,4R,6R,7R)-13-(3-furyl)-4-hydroxy-1,7-dimethyl-12-oxa-3,11-dioxotricyclo[8.4.0.0(2,7)]tetradecane-6-carboxylate (865438-59-1) + acetic acid (64-19-7,77671-22-8) → salvinorin A (83729-01-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20 ℃; for 15.5h; Inert atmosphere;

DOI:10.1021/ol800101v

Reference yield: 39.0%

16-Bromosalvinorin A (876169-02-7) + (2-phenylethyl)boronic acid (34420-17-2) → C31H36O8 + salvinorin A (83729-01-5)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 60 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/ol4027528

upstream raw materials:

acetic anhydride

salvinorin B

Episalvinorin B

C₃₀H₃₆O₉

Refernces

• 1、 Riley, Andrew P.,Day, Victor W.,Navarro, Hernan A.,Prisinzano, Thomas E.. "Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum". . p. 5936 - 5939. Retrieved 2013.
• 2、 Metz, Peter,Wang, Yuzhou,Zimdars, Patrick. "A Protecting-Group-Free Synthesis of (?)-Salvinorin A". . p. 7968 - 7973. Retrieved 2021/05/17.