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;
PubChemCID	4105431;
ChemSpider	9791461;
UNII	Z75256J75J;
CompTox Dashboard(EPA)	DTXSID20967080;
Chemical and physical data
Formula	C17H21NO5
Molar mass	319.357g·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;
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Anisodine,also known asdaturamineandα-hydroxyscopolamine,is anantispasmodicandanticholinergic drugused in the treatment ofacute circulatory shockinChina.^[1]^[2]It is atropane alkaloidand is found naturally in plants of the familySolanaceae- notablyAnisodus tanguticus(syn.Scopolia tangutica.^[3]^[2]Anisodine acts as amuscarinic acetylcholine receptor antagonistandα₁-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 ^bVarma 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.PMC1916562.PMID 2879586.
^^a ^bGanellin CR, Triggle DJ (21 November 1996).Dictionary of pharmacological agents - Google Books.CRC Press.ISBN 9780412466304.
^^a ^bChang 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.PMC1916562.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