anisodine

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.

In the Vinony graph

Vinony's link graph records 864 inbound references to anisodine, and connects out to propranolol, atropine and L-scopolamine.

It is catalogued under topics including Alpha-1 blockers, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.

Vinony links it to 6 Wikipedia language editions.

Chemical data

Formula: C17H21NO5
Molecular weight: 319.4 g/mol
IUPAC name: (9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl) 2,3-dihydroxy-2-phenylpropanoate
SMILES: CN1C2CC(CC1C3C2O3)OC(=O)C(CO)(C4=CC=CC=C4)O
InChIKey: JEJREKXHLFEVHN-UHFFFAOYSA-N
XLogP: 0.6
Polar surface area: 82.5 Å²
H-bond donors: 2
H-bond acceptors: 6
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: tropane alkaloids
Mass: 319.141972772

Show 2 more facts

chemical formula: C₁₇H₂₁NO₅
canonical SMILES: CN1C2CC(CC1C3C2O3)OC(=O)C(CO)(C4=CC=CC=C4)O

via Wikidata · CC0

~1 min read

Encyclopedic overview

3 sections

Contents

Synthesis
See also
References

== Synthesis == (-)-Anisodine can be efficiently prepared using 6-beta-acetyltropine as the starting material via a key step of the Sharpless asymmetric dihydroxylation (AD).

Excerpted from Wikipedia’s “anisodine” article, available under the CC BY-SA 4.0 licence.