CH₃CH₃

Salvinorin A

Chemistry

59 atoms · Conformer computed and published by PubChem.
Formula
C23H28O8
Molar mass
432.5 g/mol
IUPAC name
methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
InChIKey
OBSYBRPAKCASQB-AGQYDFLVSA-N

Chemistry from PubChem CID 128563.

Also known as

  • Divinorin A
  • 83729-01-5
  • Salvinorin
  • (-)-Salvinorin A
  • T56W91NG6J
  • DTXSID80232584
  • methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
  • methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo(f)isochromene-7-carboxylate

Stereoisomers

19 distinct stereoisomers are registered for this structure.

  • Salvinorin A this area CID 128563
  • methyl (2S,4aR,6aR,7R,9R,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 11546512
  • Salvinorin A (Ester) CID 21589297
  • methyl (2S,4aR,6aR,7R,9S,10aR,10bS)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 24011713
  • 12-epi-salvinorin A CID 25242485
  • methyl (2R,4aR,6aR,7R,9R,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 46831606
  • methyl (2S,4aR,6aS,7R,9S,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 97992450
  • methyl (2S,4aS,6aR,7R,9R,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 102045864
  • methyl (2S,4aR,6aR,7R,9S,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 124386697
  • methyl (2S,4aS,6aS,7R,9S,10aR,10bS)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 124425080
  • methyl (2S,4aS,6aS,7R,9S,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 125039553
  • methyl (2R,4aS,6aS,7R,9S,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 125039554
  • methyl (2R,4aS,6aS,7R,9S,10aR,10bS)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 125039555
  • methyl (2S,4aR,6aS,7R,9R,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 163000104
  • methyl (2S,4aR,6aS,7S,9R,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 163000105
  • methyl (2S,4aR,6aR,7S,9S,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 163000106
  • methyl (2S,4aR,6aS,7S,9S,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 163000107
  • methyl (2S,4aS,6aS,7R,9R,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 163000108
  • methyl (2S,4aR,6aS,7R,9S,10aR,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate CID 163000109
  • methyl 9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate mixture CID 3969708

A single natural diastereomer with seven defined stereocentres. The arrangement is not incidental — salvinorin A is a κ-opioid agonist despite containing no nitrogen at all, which is unheard of for an opioid ligand, and the activity depends on that exact geometry.

Photographs

sample About half a gram of 25x Salvia divinorum extract: dark green-black fortified leaf fragments, shown against a centimeter ruler for scale.
About half a gram of 25x Salvia divinorum extract: dark green-black fortified leaf fragments, shown against a centimeter ruler for scale.
Pie4all88 ·Public domain
sample Fresh Salvia divinorum leaves scanned flat: serrated oval blades tapering into winged stalks — the plant material that contains salvinorin A.
Fresh Salvia divinorum leaves scanned flat: serrated oval blades tapering into winged stalks — the plant material that contains salvinorin A.
Joel Keifer ·Public domain
sample Salvia divinorum growing in Mexico, showing the large veined leaves and purple-and-white flower spike of the source plant of salvinorin A.
Salvia divinorum growing in Mexico, showing the large veined leaves and purple-and-white flower spike of the source plant of salvinorin A.
Juan Carlos Pérez Magaña ·CC BY-SA
sample Salvia divinorum flower: a white, hairy corolla emerging from a violet calyx. Flowering is uncommon in cultivation and helps confirm the species.
Salvia divinorum flower: a white, hairy corolla emerging from a violet calyx. Flowering is uncommon in cultivation and helps confirm the species.
Alexander Abair ·CC BY
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