:Anisodine

{{Short description|Chemical compound}}

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{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 457811074

| IUPAC_name = 9-methyl-3-oxa-9-azatricyclo[3.2.1.02,4]non-7-yl α-hydroxy-α-(hydroxymethyl)benzeneacetate

| image = Anisodine.png

| image_class = skin-invert-image

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 52646-92-1

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

| UNII = Z75256J75J

| ATC_prefix = none

| ATC_suffix =

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C17H21NO5/c1-18-12-7-11(8-13(18)15-14(12)23-15)22-16(20)17(21,9-19)10-5-3-2-4-6-10/h2-6,11-15,19,21H,7-9H2,1H3/t11?,12-,13+,14-,15+,17-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JEJREKXHLFEVHN-QDXGGTILSA-N

| PubChem = 4105431

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9791461

| C=17 | H=21 | N=1 | O=5

| smiles = O=C(OC1CC2N(C(C1)C3OC23)C)C(O)(c4ccccc4)CO

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Anisodine, also known as daturamine and α-hydroxyscopolamine, is an antispasmodic and anticholinergic drug used in the treatment of acute circulatory shock in China.{{cite journal | vauthors = Varma DR, Yue TL | title = Adrenoceptor blocking properties of atropine-like agents anisodamine and anisodine on brain and cardiovascular tissues of rats | journal = British Journal of Pharmacology | volume = 87 | issue = 3 | pages = 587–594 | date = March 1986 | pmid = 2879586 | pmc = 1916562 | doi = 10.1111/j.1476-5381.1986.tb10201.x }}{{cite book | url = https://books.google.com/books?id=DeX7jgInYFMC&q=anisodine&pg=RA1-PA152 | title = Dictionary of pharmacological agents - Google Books | isbn = 9780412466304 | vauthors = Ganellin CR, Triggle DJ | date = 21 November 1996 | publisher = CRC Press }} It is a tropane alkaloid and is found naturally in plants of the family Solanaceae - notably Anisodus tanguticus (syn. Scopolia tangutica.{{cite journal | vauthors = Chang J, Xie W, Wang L, Ma N, Cheng S, Xie J | title = An efficient approach to the asymmetric total synthesis of (-)-anisodine | journal = European Journal of Medicinal Chemistry | volume = 41 | issue = 3 | pages = 397–400 | date = March 2006 | pmid = 16414152 | doi = 10.1016/j.ejmech.2005.12.001 }} Anisodine acts as a muscarinic acetylcholine receptor antagonist and α1-adrenergic receptor antagonist.

Synthesis

(-)-Anisodine can be efficiently prepared using 6-beta-acetyltropine as the starting material via a key step of the Sharpless asymmetric dihydroxylation (AD).

See also

References

{{reflist|30em}}

{{Adrenergic receptor modulators}}

{{Muscarinic acetylcholine receptor modulators}}

Category:Alpha-1 blockers

Category:Epoxides

Category:Muscarinic antagonists

Category:Tropane alkaloids

Category:Tropane alkaloids found in Solanaceae

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