Anisodine

Anisodine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 9-methyl-3-oxa-9-azatricyclo[3.2.1.02,4]non-7-yl α-hydroxy-α-(hydroxymethyl)benzeneacetate;
CAS Number	52646-92-1 ;
PubChem CID	4105431;
ChemSpider	9791461 ;
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 ; Key:JEJREKXHLFEVHN-QDXGGTILSA-N ;
	(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]

References

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

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[pmid2879586-1] 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.

[urlDictionary_of_pharmacological_agents_-_Google_Books-2] Ganellin CR, Triggle DJ (21 November 1996). Dictionary of pharmacological agents - Google Books. CRC Press. ISBN 9780412466304.

[pmid16414152-3] 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.

[1]

[2]

[3]

Synthesis

See also

References