Chemistry:Anisodine

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Short description: Chemical compound
Anisodine
Anisodine.png
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H21NO5
Molar mass319.357 g·mol−1
3D model (JSmol)
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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 .[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]

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

  1. 1.0 1.1 "Adrenoceptor blocking properties of atropine-like agents anisodamine and anisodine on brain and cardiovascular tissues of rats". British Journal of Pharmacology 87 (3): 587–594. March 1986. doi:10.1111/j.1476-5381.1986.tb10201.x. PMID 2879586. 
  2. 2.0 2.1 Dictionary of pharmacological agents - Google Books. CRC Press. 21 November 1996. ISBN 9780412466304. https://books.google.com/books?id=DeX7jgInYFMC&q=anisodine&pg=RA1-PA152. 
  3. 3.0 3.1 "An efficient approach to the asymmetric total synthesis of (-)-anisodine". European Journal of Medicinal Chemistry 41 (3): 397–400. March 2006. doi:10.1016/j.ejmech.2005.12.001. PMID 16414152.