CAS 83729-01-5|methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate|Salvinorin A|salvinorin A|Salvinorin A|(2S...

General Information

Structure

Molecular Formula

C₂₃H₂₈O₈

Molecular Mass

432.46362

Exact Mass

432.17841786

Charge

InChI

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

InChIKey

OBSYBRPAKCASQB-AGQYDFLVSA-N

Canonic Smiles

COC(=O)[C@@H]1C[C@H](OC(=O)C)C(=O)[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)C[C@H](OC1=O)c1cocc1

Isomeric Smiles

O=C(OC)[C@H]1[C@@]2(CC[C@H]3C(=O)O[C@H](c4ccoc4)C[C@@]3([C@H]2C(=O)[C@@H](OC(=O)C)C1)C)C

Calculated Properties

JChem

H Acceptors

Acid pKa

16.451683

H Donor

LogD (pH = 5.5)

2.3890138

LogD (pH = 7.4)

2.3890138

Log P

2.3890138

Molar Refractivity

105.9954

Polarizability

42.497757

Polar Surface Area

109.11

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC name

methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

Synonyms

Salvinorin ASalvinorin A(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(-)-Salvinorin 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 EsterDivinorin ASalvinorin(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

IUPAC Traditional name

salvinorin A

Names and Identifiers

Registration numbers

CHEMBL

PubChem CID

Chemspider ID

CAS Number

IUPHAR ligand ID

Wikipedia Title

MDL Number

PubChem SID

Registration numbers

Properties

Physical Property

Boiling Point

760.2°C (1400.36°F)

Optical Rotation

-45.3 °C at 22 deg C/D (c = 8.530 CHCl3); -41 °C at 25° C/D (c = 1 in CHCl3)

Solubility

25.07 mg/L at 25 °C (water, est)

ethanol: ~3 mg/mL

DMSO: ≥10 mg/mL

Melting Point

238-240 °C (460.4-464°F) (also reported 242-244 °C)

Apperance

white film

Pharmacology Properties

Admin Routes

Buccal/Sublingual, Smoked

Protein Bound

κ-opioid receptor

Legal Status

Uncontrolled (though Salvia divinorum is controlled in some parts of the world, such as in certain states in the US)

Gene Information

human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Oprk1(29335)

Product Information

Empirical Formula (Hill Notation)

C23H28O8

Purity

≥98% (HPLC)

Certificate of Analysis

Download link

Safety Information

MSDS Link

Download link

German water hazard class

RTECS

QL6127142

Storage Condition

protect from light

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Storage Temperature

-20°C

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Salvinorin_A

Sigma Aldrich

S8071

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.

TRC

S100900

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.

Molecule Details

References

PubChem Literature

From Data Sources

• Stewart, D. et al.: Arzneim. Forsch., 56, 269 (2006)

• Rothman, R.B. et al.: J. Pharmacol. Exp. Therap., 320, 801 (2006)

• Sheffler, D. et al.: Trends Pharamacol. Sci., 24, 107 (2006)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC name

methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

Synonyms

IUPAC Traditional name

salvinorin A

Registration numbers

CHEMBL

PubChem CID

Chemspider ID

CAS Number

IUPHAR ligand ID

Wikipedia Title

MDL Number

PubChem SID

Properties

Physical Property

Boiling Point

760.2°C (1400.36°F)

Optical Rotation

-45.3 °C at 22 deg C/D (c = 8.530 CHCl3); -41 °C at 25° C/D (c = 1 in CHCl3)

Solubility

25.07 mg/L at 25 °C (water, est)

ethanol: ~3 mg/mL

DMSO: ≥10 mg/mL

Melting Point

238-240 °C (460.4-464°F) (also reported 242-244 °C)

Apperance

white film

Pharmacology Properties

Admin Routes

Buccal/Sublingual, Smoked

Protein Bound

κ-opioid receptor

Legal Status

Uncontrolled (though Salvia divinorum is controlled in some parts of the world, such as in certain states in the US)

Gene Information

human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Oprk1(29335)

Product Information

Empirical Formula (Hill Notation)

C23H28O8

Purity

≥98% (HPLC)

Certificate of Analysis

Download link

Safety Information

MSDS Link

Download link

German water hazard class

RTECS

QL6127142

Storage Condition

protect from light

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Storage Temperature

-20°C

Molecule Details

S8071

S100900

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.

References

PubChem Literature

From Data Sources

• Stewart, D. et al.: Arzneim. Forsch., 56, 269 (2006)

• Rothman, R.B. et al.: J. Pharmacol. Exp. Therap., 320, 801 (2006)

• Sheffler, D. et al.: Trends Pharamacol. Sci., 24, 107 (2006)

Bioactivity

PubChem BioAssay

Molecule

ID:129366