83729-01-5

Basic information

• Product Name: SALVINORIN A(P)
• Synonyms: SALVINORIN A(P);(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(3-furanyl)dodechydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester;(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester;Divinorin A;[2S-(2α,4aα,6aβ,7β,9β,10aα,10bβ)]-9-(Acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-diMethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic Acid Methyl Ester;Salvinorin;Salvinorin A solution
• CAS NO: 83729-01-5
• Molecular Formula: C₂₃H₂₈O₈
• Molecular Weight: 432.47
• EINECS: 200-835-2
• Product Categories: Opioid receptor and opioid-like receptor;Opioids;Neurochcemicals;Agonist;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 83729-01-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 238-240° (Ortega); mp 242-244° (Valdes, 1984)
• Boiling Point: 563.8°C at 760 mmHg
• Flash Point: 2℃
• Appearance: white/
• Density: 1.28g/cm³
• Vapor Pressure: 9.8E-13mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: −20°C
• Solubility: DMSO: ≥10mg/mL
• CAS DataBase Reference: SALVINORIN A(P)(CAS DataBase Reference)
• NIST Chemistry Reference: SALVINORIN A(P)(83729-01-5)
• EPA Substance Registry System: SALVINORIN A(P)(83729-01-5)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 22-24/25-36/37-16
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• RTECS: QL6127142
• Hazardous Substances Data: 83729-01-5(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 83729-01-5 differently. You can refer to the following data:
1. 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.
2. 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.
3. In traditional medicine, the leaves are used for divination and for treatment of anemia and excretory functions.

Definition

ChEBI: A natural product found in Salvia divinorum.

Biological Activity

Potent naturally occuring non-nitrogenous κ -opioid selective agonist that displays high affinity at both native (K i = 4.3 nM) and cloned (K i = 16 nM) κ -opioid receptors. Also exhibits allosteric modulation of μ -opioid receptor binding. Reported to be brain-penetrant and displays psychoactive properties.

Biochem/physiol Actions

Salvinorin A is a potent, non-nitrogenous κ opioid selective receptor agonist. Salvinorin A is isolated from Salvia divinorum. Salvinorin A displays high affinity at both native (Ki=4.3 nm) and cloned (Ki=16 nm) κ -opioid receptors. Preliminary studies suggest that Salvanorin A is chemically unique among the psychtropic drugs and does not bind to any known receptor.

InChI:InChI=1/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

Upstream product

• 865438-59-1 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 
• 64-19-7 acetic acid 
• 876169-02-7 16-Bromosalvinorin A 
• 34420-17-2 (2-phenylethyl)boronic acid 
• 92545-29-4 (3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-5,6-dihydroxy-4a,8a-dimethyl-1-oxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester 
• 947596-82-9 C₃₀H₃₈O₈ 
• 947596-90-9 C₃₀H₃₆O₈ 

Downstream Products

• 689295-71-4 Salvinorinyl-2-propionate 

Relevant articles and documents

Total Synthesis of (?)-Salvinorin A

Salvinorin A (1) is natural hallucinogen that binds the human κ-opioid receptor. A total synthesis has been developed that parlays the stereochemistry of l-(+)-tartaric acid into that of (?)-1 via an unprecedented allylic dithiane intramolecular Diels–Alder reaction to obtain the trans-decalin scaffold. Tsuji allylation set the C9 quaternary center and a late-stage stereoselective chiral ligand-assisted addition of a 3-titanium furan upon a C12 aldehyde/C17 methyl ester established the furanyl lactone moiety. The tartrate diol was finally converted into the C1,C2 keto-acetate.

Divinorium A, a Psychotropic Terpenoid, and Divinorin B from the Hallucinogenic Mexican Mint Salvia Divinorum

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Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A

(Chemical Equation Presented) Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective K-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.