Scopine

Names

IUPAC name

(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.0^2,4]nonan-7-ol

Other names

6,7-Epoxytropine; Scopanol; Scopin; 6β,7β-Epoxy-1αH,5αH-tropan-3α-ol

Identifiers

498-45-3^Y

Jmol interactive 3D

InChI=1S/C8H13NO2/c1-9-5-2-4(10)3-6(9)8-7(5)11-8/h4-8,10H,2-3H2,1H3/t4-,5-,6+,7-,8+
Key: FIMXSEMBHGTNKT-RZVDLVGDSA-N
InChI=1/C8H13NO2/c1-9-5-2-4(10)3-6(9)8-7(5)11-8/h4-8,10H,2-3H2,1H3/t4-,5-,6+,7-,8+
Key: FIMXSEMBHGTNKT-RZVDLVGDBU

SMILES

O[C@@H]1C[C@H]2N(C)[C@@H](C1)[C@@H]3O[C@H]23

Properties

Chemical formula

C₈H₁₃NO₂

Molar mass

155.20 g·mol⁻¹

Melting point

75 to 76 °C (167 to 169 °F; 348 to 349 K)^[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Scopine is a tropane alkaloid found in a variety of plants including Mandragora root,^[2] Senecio mikanoides (Delairea odorata),^[3] Scopolia carniolica,^[4] and Scopolia lurida.^[5]

Scopine can be prepared by the hydrolysis of scopolamine.^[1]^[6]^[7]

References

1 2 Werner, Gottfried; Schmidt, K.-H. (1967). "Die darstellung von scopin aus scopolamin". Tetrahedron Letters 8 (14): 1283–1284. doi:10.1016/S0040-4039(00)90685-3.
↑ Staub, H. (1962). "The chemical constituents of the Mandragora root. II. The alkaloids". Helvetica Chimica Acta 45 (7): 2297–2305. doi:10.1002/hlca.19620450703.
↑ Adams, Roger; Gianturco, Maurizio (1957). "Senecio alkaloids: mikanoidine, the alkaloid from Senecio mikanoides". Journal of the American Chemical Society 79: 166–169. doi:10.1021/ja01558a045.
↑ Bendik, I.; Bauerova, O.; Bauer, S.; Mokry, J.; Tomko, J. (1958). "Alkaloids from Scopolia carniolica". Chemicke Zvesti 12: 181–184.
↑ Szymanska, Miroslawa (1967). "Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine". Acta Poloniae Pharmaceutica 24 (1): 59–64.
↑ Meinwald, J.; Chapman, O. L. (1957). "Alkaline hydrolysis of scopolamine methoxymethochloride: a new route to scopine". Journal of the American Chemical Society 79 (3): 665–666. doi:10.1021/ja01560a042.
↑ Willstatter, Richard; Berner, Endre (1923). "Hydrolysis of scopolamine". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 56B (5): 1079–1082. doi:10.1002/cber.19230560515.

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