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Anisodine

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Anisodine
Clinical data

ATC code	none
Identifiers
IUPAC name 9-methyl-3-oxa-9-azatricyclo[3.2.1.0^2,4]non-7-yl α-hydroxy-α-(hydroxymethyl)benzeneacetate
CAS Number	52646-92-1^N
PubChemCID	4105431
ChemSpider	9791461^Y
UNII	Z75256J75J
CompTox Dashboard(EPA)	DTXSID20967080
Chemical and physical data
Formula	C₁₇H₂₁NO₅
Molar mass	319.357 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OC1CC2N(C(C1)C3OC23)C)C(O)(c4ccccc4)CO
InChI InChI=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^Y Key:JEJREKXHLFEVHN-QDXGGTILSA-N^Y
^NY (what is this?) (verify)

Anisodine, also known asdaturamine andα-hydroxyscopolamine, is anantispasmodic andanticholinergic drug used in the treatment ofacute circulatory shock inChina.^[1]^[2] It is atropane alkaloid and is found naturally in plants of the familySolanaceae - notablyAnisodus tanguticus (syn.Scopolia tangutica.^[3]^[2] Anisodine acts as amuscarinic acetylcholine receptor antagonist andα₁-adrenergic receptor antagonist.^[1]

Synthesis

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(-)-Anisodine can be efficiently prepared using 6-beta-acetyltropine as the starting material via a key step of the Sharpless asymmetric dihydroxylation (AD).^[3]