Anisodine

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
ChemSpider
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
 X markNcheckY (what is this?)  (verify)

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

Compound medications

Anisodine/procaine is an injected prescription drug in China, approved for "ischemic optic nerve, retinal, and choroidal lesions". It is believed to work by reliving vascular spasms.

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

  1. 1 2 Varma DR, Yue TL (March 1986). "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. doi:10.1111/j.1476-5381.1986.tb10201.x. PMC 1916562. PMID 2879586.
  2. 1 2 Ganellin CR, Triggle DJ (21 November 1996). Dictionary of pharmacological agents - Google Books. CRC Press. ISBN 9780412466304.
  3. 1 2 Chang J, Xie W, Wang L, Ma N, Cheng S, Xie J (March 2006). "An efficient approach to the asymmetric total synthesis of (-)-anisodine". European Journal of Medicinal Chemistry. 41 (3): 397–400. doi:10.1016/j.ejmech.2005.12.001. PMID 16414152.
  4. ↑ "复方樟柳碱注射液说明书 [第五批化学药品说明书]" [Package insert for compound anisodine solution for injection [NMPA-standard package inserts for chemical drugs, volume 5]]. National Medical Products Administration.