Chemistry:Anisodamine

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Anisodamine, also known as (6S)-6-hydroxyhyoscyamine, is a mAChR anticholinergic and α1 adrenergic receptor antagonist used 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] It is injected to treat acute circulatory shock,[1] used orally to treat smooth muscle spasms in the GI tract,[3] and as an eye drop at 0.5% concentration for slowing the progression of myopia.[4]

Anisodamine is a naturally occurring tropane alkaloid found in some plants of the family Solanaceae including Datura.[5] Its English name anisodamine and its Mandarin Chinese name 山莨菪碱 are given after Anisodus tanguticus (Chinese: 山莨菪; pinyin: shān làng dàng).[6][7]

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,[8] causes less mydriasis, but has approximately equal or slightly lower potency in blocking spasms and in reducing GI motility.[9] Chinese textbooks consider it to have a similar spectrum of effects on humans.[10] 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.[11]

Chemical identity

The natural alkaloid

Sources appear to disagree on the identity of anisodamine, specifically on the description of the hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl ring. The first thing they disagree on is whether the substance is 6- or 7-hydroxy, though because the ring is symmetric the two numberings are equivalent: all of these assignments yield the same InChI connectivity layer and the corresponding InChIKey "main" segment (WTQYWNWRJNXDEG).

More problematic is the assignment of stereochemistry. Chemspider (which this article's infobox is largely based on) uses a structure similar to PubChem CID 183088, with (1S,3S,5S,7S)-7-hydroxy or (1S,3S,5S,6S)-6-hydroxy (InChI t12-,13+,14-,15+,16+/m1). However, as of April 2026, the name "anisodamine" is assigned by PubChem to CID 6918612, (1R,3S,5R,6S)-6-hydroxy (InChI t12-,13-,14+,15+,16-/m0); FDA UNII has the same assignment.

The Chinese pharmacopoeia describes anisodamine HBr as a C17H23NO4•HBr derived from Anisodus tanguticus without mentioning its exact conformation. It includes the CAS number 55449-49-5,[12] which returns the (1R,3S,5R,6S) on both PubChem and ChemSpider.

The racemer

The Chinese pharmacopoeia describes racanisodamine as "(±)-6β-hydroxy-1αH,5αH-tropin-3-yl tropate ester" with CAS number 17659-49-3.[13]

See also

References

  1. ↑ 1.0 1.1 "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. March 1986. doi:10.1111/j.1476-5381.1986.tb10201.x. PMID 2879586. 
  2. ↑ "Pharmacopoeia Search: "山莨菪碱"". 中国药典. http://db2.ouryao.com/yd2015/index.php?k=%E5%B1%B1%E8%8E%A8%E8%8F%AA%E7%A2%B1. 
  3. ↑ "消旋山莨菪碱片说明书, 第二批国家非处方药化学药品使用说明书目录". https://www.nmpa.gov.cn/wwwroot/otc2h/x086.htm. 
  4. ↑ "消旋山莨菪碱滴眼液防治少年儿童假性近视的疗效分析" (in zh-cn). 国际医药卫生导报 14 (15): 67–68. 2008. doi:10.3760/cma.j.issn.1007-1245.2008.15.027. http://med.wanfangdata.com.cn/Paper/Detail?id=PeriodicalPaper_gjyywsdb200815027. Retrieved 2017-12-03. 
  5. ↑ "Simultaneous determination of atropine, scopolamine, and anisodamine in Flos daturae by capillary electrophoresis using a capillary coated by graphene oxide". Journal of Separation Science 36 (16): 2698–2702. August 2013. doi:10.1002/jssc.201300304. PMID 23868645. 
  6. ↑ "消旋山莨菪碱" (in zh-CN). 中国药典. http://db2.ouryao.com/yd2015/view.php?v=txt&id=4045. 
  7. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named imm
  8. ↑ "Differential neuropsychopharmacological influences of naturally occurring tropane alkaloids anisodamine versus scopolamine". Neuroscience Letters 443 (3): 241–245. October 2008. doi:10.1016/j.neulet.2008.07.048. PMID 18672024. 
  9. ↑ "The pharmacological properties of anisodamine". Journal of Applied Toxicology 27 (2): 116–121. March 2007. doi:10.1002/jat.1154. PMID 17186568. 
  10. ↑ "第八章 作用于胆碱受体药物 [8 Agents acting on acetylcholine receptors]" (in zh). 麻醉药理学 (4 ed.). Beijing: 人民卫生出版社. 2016. p. 133. ISBN 978-7-117-22701-8. 
  11. ↑ "Update on the sources, pharmacokinetics, pharmacological action, and clinical application of anisodamine". Biomedicine & Pharmacotherapy 161. May 2023. doi:10.1016/j.biopha.2023.114522. PMID 37002581. 
  12. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named chp25hbr
  13. ↑ "消旋山莨菪碱 Raceanisodamine". 中华人民共和国药典. 2 (2025 ed.). ISBN 9787521451917. https://db2.ouryao.com/yd2025/view.php?id=6f9a36b47de3acd09f3139f14705fb05. "C17H23NO4 305.37［17659-49-3］本品为（±）-6β-羟基-1αH，5αH-托品-3-醇托品酸酯。按干燥品计算，含C17H23NO4不得少于99.0%。" 



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