Anisodamine

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.^[1] It is given orally or by injection, as a racemic mixture (racanisodamine) or as a hydrobromide salt of the natural enantiometer.^[2] Eye drops at 0.5% concentration for slowing the progression of myopia is also available in China.^[3]

Other names7β-hydroxyhyoscyamine

ATC code

• None

CAS Number

• 55869-99-3 ^Y

PubChem CID

• 183088

Quick facts Clinical data, Other names ...

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
ECHA InfoCard	100.164.962
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 is a naturally occurring tropane alkaloid found in some plants of the family Solanaceae including Datura.^[4] Its Mandarin Chinese name 山莨菪碱 is given after Anisodus tanguticus (Chinese: 山莨菪; pinyin: shān làng dàng).^[5]

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,^[6] causes less mydriasis, but has approximately equal or slightly lower potency in blocking spasms and in reducing GI motility.^[7] Chinese textbooks consider it to have a similar spectrum of effects on humans.^[8] 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.^[9]