Anisodamine

Anisodamine

Clinical data
Other names	7β-hydroxyhyoscyamine
ATC code	None
Identifiers
IUPAC name [(1S,3S,5S,7S)-7-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenyl-propanoate
CAS Number	55869-99-3 Y
PubChem CID	183088
ChemSpider	159209 Y
UNII	01343Q8EL8
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C17H23NO4
Molar mass	305.374 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(O[C@@H]1C[C@@H]2N(C)[C@H](C1)C[C@@H]2O)[C@@H](c3ccccc3)CO
InChI InChI=1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13+,14-,15+,16+/m1/s1 Y Key:WTQYWNWRJNXDEG-LEOABGAYSA-N Y
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Anisodamine, also known as 7β-hydroxyhyoscyamine, is a mAChR anticholinergic and α₁ adrenergic receptor antagonist used in the treatment of acute circulatory shock in China. It is given orally or by injection, as a racemic mixture (racanisodamine) or as a hydrobromide salt of the natural enantiometer. Eye drops at 0.5% concentration for slowing the progression of myopia is also available in China.

Anisodamine is a naturally occurring tropane alkaloid found in some plants of the family Solanaceae including Datura. Its Mandarin Chinese name 山莨菪碱 is given after Anisodus tanguticus (Chinese: 山莨菪; pinyin: shān làng dàng).

In rodents, anisodamine is more "selective" in its action compared to atropine. It poorly passes the blood-brain barrier and binds brain mAChR less tightly. In rodents, it exhibits weaker CNS effects, causes less mydriasis, but has approximately equal or slightly lower potency in blocking spasms and in reducing GI motility. Chinese textbooks consider it to have a similar spectrum of effects on humans. As a result, it (or rather, its synthetic racemic version) is widely used in China. It was added to China's national Essential Medicine List in 2012.

See also

• Anisodine
• Atropine, used for similar cardiac and optamological purposes elsewhere
• Hyoscyamine