Salvinorin A

Chemistry

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.