Anisodine

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
PubChem CID	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 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

• Anisodamine
• Scopolamine

References

1. 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. Ganellin CR, Triggle DJ (21 November 1996). Dictionary of pharmacological agents - Google Books. CRC Press. ISBN 9780412466304.
3. 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.