Scopine

Scopine
Names
	IUPAC name 6β,7β-Epoxytropan-3α-ol
	Systematic IUPAC name (1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol
	Other names 6,7-Epoxytropine; Scopanol; Scopin; 6β,7β-Epoxy-1αH,5αH-tropan-3α-ol
Identifiers
CAS Number	498-45-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL4303435; ChEMBL4303536;
ChemSpider	20067940;
PubChem CID	1274465;
UNII	Z5LGM3Q28U ;
CompTox Dashboard (EPA)	DTXSID801030466 ;
	InChI 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;
	SMILES O[C@@H]1C[C@H]2N(C)[C@@H](C1)[C@@H]3O[C@H]23;
Properties
Chemical formula	C8H13NO2
Molar mass	155.197 g·mol−1
Melting point	75 to 76 °C (167 to 169 °F; 348 to 349 K)
	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 mikanioides (Delairea odorata),^[3] Scopolia carniolica,^[4] and Scopolia lurida.^[5]

Scopine can be prepared by the hydrolysis of scopolamine.^[1]^[6]^[7] It can also be prepared in three steps from N-methoxycarbonylpyrrole and 1,1,3,3-tetrabromoacetone; the reagents are combined in a [4+3] cycloaddition, followed by a diastereoselective reduction with diisobutylaluminum hydride, and finally a Prilezhaev epoxidation with trifluoroperacetic acid affords scopine.^[8]

References

^ ^a ^b 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. PMID 6044210.
^ 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 B. 56 (5): 1079–1082. doi:10.1002/cber.19230560515.
^ Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. (1978). "Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reaction". J. Am. Chem. Soc. 100 (6): 1786–1791. doi:10.1021/ja00474a021.

[Werner-1] 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. PMID 6044210.

[2] 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.

[3] 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.

[4] Bendik, I.; Bauerova, O.; Bauer, S.; Mokry, J.; Tomko, J. (1958). "Alkaloids from Scopolia carniolica". Chemicke Zvesti. 12: 181–184.

[5] Szymanska, Miroslawa (1967). "Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine". Acta Poloniae Pharmaceutica. 24 (1): 59–64.

[6] 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.

[7] Willstatter, Richard; Berner, Endre (1923). "Hydrolysis of scopolamine". Berichte der Deutschen Chemischen Gesellschaft B. 56 (5): 1079–1082. doi:10.1002/cber.19230560515.

[8] Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. (1978). "Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reaction". J. Am. Chem. Soc. 100 (6): 1786–1791. doi:10.1021/ja00474a021.

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See also

References