Anisodine

Chemical compound From Wikipedia, the free encyclopedia

Anisodine, also known as daturamine and α-hydroxyscopolamine, is an antispasmodic and anticholinergic drug used in the treatment of acute circulatory shock in China.[1][2] It is a tropane alkaloid and is found naturally in plants of the family Solanaceae - notably Anisodus tanguticus (syn. Scopolia tangutica.[3][2] Anisodine acts as a muscarinic acetylcholine receptor antagonist and α1-adrenergic receptor antagonist.[1]

ATC code
  • none
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Anisodine
Clinical data
ATC code
  • none
Identifiers
  • 9-methyl-3-oxa-9-azatricyclo[3.2.1.02,4]non-7-yl α-hydroxy-α-(hydroxymethyl)benzeneacetate
CAS Number
PubChem CID
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UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H21NO5
Molar mass319.357 g·mol−1
3D model (JSmol)
  • O=C(OC1CC2N(C(C1)C3OC23)C)C(O)(c4ccccc4)CO
  • 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 checkY
  • Key:JEJREKXHLFEVHN-QDXGGTILSA-N checkY
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Synthesis

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

See also

References

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