Scopine

{{Chembox

| ImageFileL1 = Scopine.svg

| ImageClassL1 = skin-invert-image

| ImageFileR1 = Scopine_3D.png

| IUPACName = 6β,7β-Epoxytropan-3α-ol

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

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

|Section1={{Chembox Identifiers

| CASNo = 498-45-3

| CASNo_Ref = {{cascite|correct|}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z5LGM3Q28U

| ChEMBL = 4303435

| ChEMBL1 = 4303536

| PubChem = 1274465

| ChemSpiderID = 20067940

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

| StdInChI = 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+

| StdInChIKey = FIMXSEMBHGTNKT-RZVDLVGDSA-N

}}

|Section2={{Chembox Properties

| C=8|H=13|N=1|O=2

| Appearance =

| Density =

| MeltingPtC = 75 to 76

| MeltingPt_ref = {{cite journal | author = Werner, Gottfried | journal = Tetrahedron Letters | year = 1967 | issue = 14 | pages = 1283–1284 | doi = 10.1016/S0040-4039(00)90685-3 | title = Die darstellung von scopin aus scopolamin | last2 = Schmidt | first2 = K.-H. | volume = 8| pmid = 6044210 }}

| BoilingPtC =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Scopine is a tropane alkaloid found in a variety of plants including Mandragora root,{{Cite journal | author = Staub, H. | title = The chemical constituents of the Mandragora root. II. The alkaloids | journal = Helvetica Chimica Acta | year = 1962 | volume = 45| pages = 2297–2305 | doi = 10.1002/hlca.19620450703 | issue = 7}} Senecio mikanioides (Delairea odorata),{{Cite journal |author1=Adams, Roger |author2=Gianturco, Maurizio | title = Senecio alkaloids: mikanoidine, the alkaloid from Senecio mikanoides | journal = Journal of the American Chemical Society | year = 1957 | volume = 79 | pages = 166–169 | doi = 10.1021/ja01558a045}} Scopolia carniolica,{{Cite journal |author1=Bendik, I. |author2=Bauerova, O. |author3=Bauer, S. |author4=Mokry, J. |author5=Tomko, J. | title = Alkaloids from Scopolia carniolica | journal = Chemicke Zvesti | year = 1958 | volume = 12 | pages = 181–184}} and Scopolia lurida.{{Cite journal | author = Szymanska, Miroslawa | title = Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine | journal = Acta Poloniae Pharmaceutica | year = 1967 | volume = 24 | issue = 1 | pages = 59–64}}

Scopine can be prepared by the hydrolysis of scopolamine.{{Cite journal |author1=Meinwald, J. |author2=Chapman, O. L. | title = Alkaline hydrolysis of scopolamine methoxymethochloride: a new route to scopine | journal = Journal of the American Chemical Society | year = 1957 | volume = 79 | pages = 665–666 | doi = 10.1021/ja01560a042 | issue = 3}}{{Cite journal |author1=Willstatter, Richard |author2=Berner, Endre | title = Hydrolysis of scopolamine | journal = Berichte der Deutschen Chemischen Gesellschaft B | year = 1923 | volume = 56 | pages = 1079–1082 | doi = 10.1002/cber.19230560515 | issue = 5}} 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.{{cite journal|last1 = Hayakawa|first1 = Y.|last2 = Baba|first2 = Y.|last3 = Makino|first3 = S.|last4 = Noyori|first4 = R.|journal = J. Am. Chem. Soc.|year = 1978|volume = 100|issue = 6|pages = 1786–1791|title = Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reaction|doi = 10.1021/ja00474a021}}

File:HKRedSynth.png