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Anisodamine

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Anisodamine
Image
Clinical data
Other names(6S)-6-hydroxyhyoscyamine,[1] (-)-6β-hydroxyhyoscyamine[2]
ATC code
  • None
Pharmacokinetic data
Bioavailabilitylow (oral)[3]
Excretionwhen oral: urine (2%), feces (>90%)[3]
Identifiers
  • [(1S,3S,5S,7S)-7-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenyl-propanoate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.164.962 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO4
Molar mass305.374 g·mol−1
3D model (JSmol)
Specific rotation9.0–11.5°[4]
  • O=C(O[C@@H]1C[C@@H]2N(C)[C@H](C1)C[C@@H]2O)[C@@H](c3ccccc3)CO
  • 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 checkY
  • Key:WTQYWNWRJNXDEG-LEOABGAYSA-N checkY
  (verify)

Anisodamine, also known as (6S)-6-hydroxyhyoscyamine, is a mAChR anticholinergic and α1 adrenergic receptor antagonist used in China.[5] It is given orally or by injection, as a racemic mixture (racanisodamine) or as a hydrobromide salt of the natural enantiometer.[6] It is injected to treat acute circulatory shock,[5] 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.[7]

Anisodamine is a naturally occurring tropane alkaloid found in some plants of the family Solanaceae including Datura.[8] 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).[9][1]

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,[10] causes less mydriasis, but has approximately equal or slightly lower potency in blocking spasms and in reducing GI motility.[11] Chinese textbooks consider it to have a similar spectrum of effects on humans.[12] 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.[13]

Chemical identity

[edit]

The natural alkaloid

[edit]

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,[4] which returns the (1R,3S,5R,6S) on both PubChem and ChemSpider.

The racemer

[edit]

The Chinese pharmacopoeia describes racanisodamine as "(±)-6β-hydroxy-1αH,5αH-tropin-3-yl tropate ester" with CAS number 17659-49-3.[14]

See also

[edit]

References

[edit]
  1. ^ a b "新药氢溴酸山莨菪碱 (包括天然品 654 及合成品 654-2)" [New drug anisodamine HBr (including natural "654" and synthetic "654-2")]. www.imm.ac.cn. Institute of Chinese Materia Medica. 2021-11-18. 化学研究证明At-2的化学结构为6S-羟基莨菪碱。因此，根据其来源的植物学名于是命名为山莨菪碱（anisodamine）。
  2. ^ UNII 01343Q8EL8
  3. ^ a b c "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" [Packet insert for Racanisodamine tablets in the National Catalog of Packet Inserts for Non-Prescription Chemical Drugs Volume 2]. National Medical Products Administration.
  4. ^ a b "氢溴酸山莨菪碱 Anisodamine Hydrobromide". 中华人民共和国药典 [Pharmacopoeia of the People's Republic of China]. Vol. 2 (2025 ed.). ISBN 9787521451917.
  5. ^ a b 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. PMC 1916562. PMID 2879586.
  6. ^ "Pharmacopoeia Search: "山莨菪碱"". 中国药典.{{cite web}}: CS1 maint: deprecated archival service (link)
  7. ^ "消旋山莨菪碱滴眼液防治少年儿童假性近视的疗效分析". 国际医药卫生导报 (in Chinese (China)). 14 (15): 67–68. 2008. doi:10.3760/cma.j.issn.1007-1245.2008.15.027. Archived from the original on 2023-03-27. Retrieved 2017-12-03.
  8. ^ Ye N, Li J, Gao C, Xie Y (August 2013). "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. doi:10.1002/jssc.201300304. PMID 23868645.
  9. ^ "消旋山莨菪碱" (in Chinese (China)). 中国药典. Retrieved 3 December 2017.{{cite web}}: CS1 maint: deprecated archival service (link)
  10. ^ Zhang WW, Song MK, Cui YY, Wang H, Zhu L, Niu YY, et al. (October 2008). "Differential neuropsychopharmacological influences of naturally occurring tropane alkaloids anisodamine versus scopolamine". Neuroscience Letters. 443 (3): 241–245. doi:10.1016/j.neulet.2008.07.048. PMID 18672024. S2CID 2730169.
  11. ^ Poupko JM, Baskin SI, Moore E (March 2007). "The pharmacological properties of anisodamine". Journal of Applied Toxicology. 27 (2): 116–121. doi:10.1002/jat.1154. PMID 17186568.
  12. ^ DAI TJ, YU T, eds. (2016). "第八章 作用于胆碱受体药物 [8 Agents acting on acetylcholine receptors]". 麻醉药理学 [Anesthesia Pharmacology] (in Chinese) (4 ed.). Beijing: 人民卫生出版社. p. 133. ISBN 978-7-117-22701-8.
  13. ^ Zhang Y, Zou J, Wan F, Peng F, Peng C (May 2023). "Update on the sources, pharmacokinetics, pharmacological action, and clinical application of anisodamine". Biomedicine & Pharmacotherapy. 161 114522. doi:10.1016/j.biopha.2023.114522. PMID 37002581.
  14. ^ "消旋山莨菪碱 Raceanisodamine". 中华人民共和国药典 [Pharmacopoeia of the People's Republic of China]. Vol. 2 (2025 ed.). ISBN 9787521451917. 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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