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]

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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]

Alkaloids