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MedKoo Cat#: 540021 | Name: Anisodamine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Anisodamine is a naturally derived tropane alkaloid with anticholinergic and vasodilatory properties, commonly used in China for the treatment of circulatory shock, gastrointestinal spasms, and organophosphate poisoning. It functions as a non-selective muscarinic acetylcholine receptor antagonist, inhibiting parasympathetic nerve impulses and thus relaxing smooth muscle and improving microcirculation. Unlike atropine, anisodamine exhibits a milder central nervous system effect and may offer cytoprotective and anti-inflammatory bioactivity, especially in ischemic and inflammatory conditions.

Chemical Structure

Anisodamine
Anisodamine
CAS#55869-99-3 (free base)

Theoretical Analysis

MedKoo Cat#: 540021

Name: Anisodamine

CAS#: 55869-99-3 (free base)

Chemical Formula: C17H23NO4

Exact Mass: 305.1627

Molecular Weight: 305.37

Elemental Analysis: C, 66.86; H, 7.59; N, 4.59; O, 20.96

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Related CAS #
131674-05-0 (HCl) 85760-60-7 (Racemic_free base) 55869-99-3 (free base) 55449-49-5 (HBr)
Synonym
Anisodamine (-); Anisodamine
IUPAC/Chemical Name
(1R,3S,5R,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (S)-3-hydroxy-2-phenylpropanoate
InChi Key
WTQYWNWRJNXDEG-RBZJEDDUSA-N
InChi Code
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-/m0/s1
SMILES Code
CN1[C@@H]2C[C@H](O)[C@H]1C[C@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
TBD
In vitro activity:
CCK-8 assay results showed that 3% CSE could induce ASM cell proliferation (p < 0.01). In contrast, anisodamine alone exhibited no cellular effects with doses up to 100 μM, but almost completely inhibited CSE-induced cell proliferation at 1 μM (Fig. 1A). As shown in Fig. 1B, HCS analysis showed that the proportion of BrdU incorporation in the S phase increased significantly in the group treated with 3% CSE (p < 0.01), whereas no significant effects were observed by anisodamine alone when its dose reached 100 μM in comparison to the control group. At the same time, anisodamine could dose-dependently influence CSE-induced BrdU incorporation, which reached a maximal inhibitory value at 1 μM, compared to that in the CSE-treated group. Similarly, high level expressions of proliferation markers Ki67 were also detected using HCS analysis in primary ASM cells stimulated with 3% CSE (p < 0.01). Such a response was significantly reversed under anisodamine treatment when the concentration reaches to 10 μM (Fig. 1C). Although it exist the difference in strength between the BrdU incorporation assay and Ki67 expression test under treatment of anosodamine, the overall trends in the expression are consistent with the influence of increasing of anosodamine's concentration. Collectively, these results demonstrated that anisodamine has some beneficial effects on prevention or reversal of CSE-induced ASM cell proliferation. Reference: Toxicol Appl Pharmacol. 2012 Jul 1;262(1):70-9. https://pubmed.ncbi.nlm.nih.gov/22561873/
In vivo activity:
Compared with the control, rats in the BLM group had higher airway resistance and elastance (P<0.01), indicating that BLM could inhibit lung function. However, Ani (Anisodamine) treatment reversed the inhibitory effect of BLM on lung function in a dose-dependent manner. Rats in the BLM + Ani 10 mg/kg group and BLM + Ani 20 mg/kg group had much lower resistance and elastance values than those in the BLM group (P<0.01) (Figure 1A,B). Reference: Ann Transl Med. 2021 May; 9(10): 859. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8184412/

Preparing Stock Solutions

The following data is based on the product molecular weight 305.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Li Z, Xu C, Tao Y, Liang Y, Liang Q, Li J, Li R, Ye H. Anisodamine alleviates lipopolysaccharide-induced pancreatic acinar cell injury through NLRP3 inflammasome and NF-κB signaling pathway. J Recept Signal Transduct Res. 2020 Feb;40(1):58-66. doi: 10.1080/10799893.2020.1713808. Epub 2020 Jan 30. PMID: 31997696. 2. Xu GN, Yang K, Xu ZP, Zhu L, Hou LN, Qi H, Chen HZ, Cui YY. Protective effects of anisodamine on cigarette smoke extract-induced airway smooth muscle cell proliferation and tracheal contractility. Toxicol Appl Pharmacol. 2012 Jul 1;262(1):70-9. doi: 10.1016/j.taap.2012.04.020. Epub 2012 Apr 26. PMID: 22561873. 3. Zhao X, Zhao B, Zhao Y, Zhang Y, Qian M. Protective effect of anisodamine on bleomycin-induced acute lung injury in immature rats via modulating oxidative stress, inflammation, and cell apoptosis by inhibiting the JAK2/STAT3 pathway. Ann Transl Med. 2021 May;9(10):859. doi: 10.21037/atm-21-1750. PMID: 34164493; PMCID: PMC8184412. 4. Du N, Liu D, Sun X, Qin S, Ren H. Anisodamine (654-2) inhibits inflammation to alleviate influenza A virus-induced acute lung injury. J Med Virol. 2021 Jun 2. doi: 10.1002/jmv.27043. Epub ahead of print. PMID: 34076913.
In vitro protocol:
1. Li Z, Xu C, Tao Y, Liang Y, Liang Q, Li J, Li R, Ye H. Anisodamine alleviates lipopolysaccharide-induced pancreatic acinar cell injury through NLRP3 inflammasome and NF-κB signaling pathway. J Recept Signal Transduct Res. 2020 Feb;40(1):58-66. doi: 10.1080/10799893.2020.1713808. Epub 2020 Jan 30. PMID: 31997696. 2. Xu GN, Yang K, Xu ZP, Zhu L, Hou LN, Qi H, Chen HZ, Cui YY. Protective effects of anisodamine on cigarette smoke extract-induced airway smooth muscle cell proliferation and tracheal contractility. Toxicol Appl Pharmacol. 2012 Jul 1;262(1):70-9. doi: 10.1016/j.taap.2012.04.020. Epub 2012 Apr 26. PMID: 22561873.
In vivo protocol:
1. Zhao X, Zhao B, Zhao Y, Zhang Y, Qian M. Protective effect of anisodamine on bleomycin-induced acute lung injury in immature rats via modulating oxidative stress, inflammation, and cell apoptosis by inhibiting the JAK2/STAT3 pathway. Ann Transl Med. 2021 May;9(10):859. doi: 10.21037/atm-21-1750. PMID: 34164493; PMCID: PMC8184412. 2. Du N, Liu D, Sun X, Qin S, Ren H. Anisodamine (654-2) inhibits inflammation to alleviate influenza A virus-induced acute lung injury. J Med Virol. 2021 Jun 2. doi: 10.1002/jmv.27043. Epub ahead of print. PMID: 34076913.
1: Li S, Feng W, Chen D, Yu L, Cui H, Li M. Revealing the gastric protective mechanism of Physochlaina physaloides (L) G. Don. with clinical orientation: PPAR/NF-κB signalling pathway activation. Phytomedicine. 2025 Mar 16;141:156642. doi: 10.1016/j.phymed.2025.156642. Epub ahead of print. PMID: 40120539. 2: Deng Y, Gao J, Mei Y, Ran WJ. Effects of racemic anisodamine in combination with orthokeratology and defocus incorporated multiple segment spectacle lenses for myopia control in adolescents. Sci Rep. 2025 Mar 13;15(1):8781. doi: 10.1038/s41598-024-84914-y. PMID: 40082447; PMCID: PMC11906783. 3: Liang H, Yan H. Atropine plus omeprazole for acute gastritis: Efficacy and safety analysis. Pak J Pharm Sci. 2024 Nov-Dec;37(6):1207-1212. PMID: 39799435. 4: Liu M, Liu H, Kang H, Wu J, Xing P, Ding X, Wei Y, Kong X. Anisodamine ameliorates crystalline silica-exposed pulmonary inflammation and fibrosis via the α7nAChR/JAK2/STAT3 signaling pathway. Ecotoxicol Environ Saf. 2025 Jan 1;289:117534. doi: 10.1016/j.ecoenv.2024.117534. Epub 2024 Dec 11. PMID: 39667322. 5: Sun B, Wang C, Wang Z, Liang J, Han K, Zhang S, Yin C, Wang X, Liu C, Feng Z, Wang S, Jiang H. Strategy for Accurate Detection of Six Tropane Alkaloids in Honey Using Lateral Flow Immunosensors. Sensors (Basel). 2024 Nov 13;24(22):7265. doi: 10.3390/s24227265. PMID: 39599042; PMCID: PMC11598261. 6: Tang F, Zhang JN, Xu LY, Zhao XL, Wan F, Ao H, Peng C. Endothelial-derived exosomes: A novel therapeutic strategy for LPS-induced myocardial damage with anisodamine. Int J Biol Macromol. 2024 Dec;282(Pt 4):136993. doi: 10.1016/j.ijbiomac.2024.136993. Epub 2024 Nov 1. PMID: 39489255. 7: Liu D, Tang F, Zhang L, Wan F, Xu LY, Zhang JN, Zhao XL, Ao H, Peng C. Anisodamine (654-1/654-2) ameliorates septic kidney injury in rats by inhibiting inflammation and apoptosis. Front Pharmacol. 2024 Sep 27;15:1421551. doi: 10.3389/fphar.2024.1421551. PMID: 39399464; PMCID: PMC11467892. 8: Tan N, Wang Y, Ren L, Tie F, Hu N, Wang H, Dong Q. Network Pharmacology and Molecular Dynamics Simulations Reveal the Mechanism of Total Alkaloid Components in Anisodus Tanguticus (Maxim.) Pascher in Treating Inflammation and Pain. Chem Biodivers. 2025 Jan;22(1):e202401199. doi: 10.1002/cbdv.202401199. Epub 2024 Nov 9. PMID: 39313870. 9: Wu R, Zhang F, Liu Y, Yu Y, Zhang J, Yao C, Dai S, Wan F, Nan F, Li Y. Comparative pharmacokinetic study of Anisodamine Hydrobromide tablets and injection in septic acute lung injury rats. Bioanalysis. 2024;16(17-18):959-972. doi: 10.1080/17576180.2024.2383106. Epub 2024 Aug 8. PMID: 39115055; PMCID: PMC11485889. 10: Zhang B, Luo L, Xiong S, Xiao Y, Zhang T, Xiang T. Anisodamine hydrobromide ameliorates acute lung injury via inhibiting pyroptosis in murine sepsis model. Immunopharmacol Immunotoxicol. 2024 Oct;46(5):662-671. doi: 10.1080/08923973.2024.2386331. Epub 2024 Aug 26. PMID: 39074955. 11: Dutertre Q, Guy PA, Sutour S, Peitsch MC, Ivanov NV, Glauser G, von Reuss S. Identification of Granatane Alkaloids from Duboisia myoporoides (Solanaceae) using Molecular Networking and Semisynthesis. J Nat Prod. 2024 Aug 23;87(8):1914-1920. doi: 10.1021/acs.jnatprod.4c00304. Epub 2024 Jul 22. PMID: 39038492; PMCID: PMC11348422. 12: Wang DF, Gao F, Xue FS. Letter to the Editor Regarding Effect of Zusanli Acupoint Injection with Anisodamine on Postoperative Recovery Quality of Patients Undergoing Bariatric Surgery. Obes Surg. 2024 Aug;34(8):3135-3136. doi: 10.1007/s11695-024-07393-0. Epub 2024 Jul 17. PMID: 39017975. 13: Jain H, Odat RM, Jain J, Dey D, Hussein AM, Marsool MDM, Shahbaz H, Mathur A, Yadav H, Passey S, Yadav R. Anisodamine for the prevention of contrast- induced nephropathy in patients with acute coronary syndrome: a pilot systematic review and meta-analysis of randomized controlled trials. Ann Med Surg (Lond). 2024 May 21;86(7):4123-4129. doi: 10.1097/MS9.0000000000002181. PMID: 38989215; PMCID: PMC11230748. 14: Liu N, Chen C, Wang B, Wang X, Zhang D, Zhou G. Exogenous regulation of macronutrients promotes the accumulation of alkaloid yield in anisodus tanguticus (Maxim.) pascher. BMC Plant Biol. 2024 Jun 26;24(1):602. doi: 10.1186/s12870-024-05299-8. PMID: 38926662; PMCID: PMC11201296. 15: Chen C, Wang B, Li J, Xiao Y, Chen K, Liu N, Zhou G. Predicting potential and quality distribution of Anisodus tanguticus (Maxim.) Pascher under different climatic conditions in the Qinghai-Tibet plateau. Front Plant Sci. 2024 Jun 3;15:1369641. doi: 10.3389/fpls.2024.1369641. PMID: 38887466; PMCID: PMC11180894. 16: Torrents-Masoliver B, Terriente-Palacios C, Bover-Cid S, Jofré A, Castellari M, Ribas-Agustí A. Effect of pH and temperature on tropane alkaloids within a processing strategy to provide safe infant cereal-based food. Food Res Int. 2024 Jul;188:114439. doi: 10.1016/j.foodres.2024.114439. Epub 2024 May 6. PMID: 38823829. 17: Wang Y, Chu Y, Dai H, Zheng Y, Chen R, Zhou C, Zhong Y, Zhan C, Luo J. Protective role of pretreatment with Anisodamine against sepsis-induced diaphragm atrophy via inhibiting JAK2/STAT3 pathway. Int Immunopharmacol. 2024 May 30;133:112133. doi: 10.1016/j.intimp.2024.112133. Epub 2024 Apr 23. PMID: 38652962. 18: Mateus ARS, Crisafulli C, Cruz Barros S, Pena A, Sanches Silva A. Development and validation of an analytical method based on QuEChERS followed by UHPLC-ToF-MS for the determination of tropane alkaloids in buckwheat (Fagopyrum esculentum L.) and buckwheat products. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2024 Jun;41(6):648-663. doi: 10.1080/19440049.2024.2339325. Epub 2024 Apr 18. PMID: 38635926. 19: Gou Y, Jing Y, Song J, Nagdy MM, Peng C, Zeng L, Chen M, Lan X, Htun ZLL, Liao Z, Li Y. A novel bHLH gene responsive to low nitrogen positively regulates the biosynthesis of medicinal tropane alkaloids in Atropa belladonna. Int J Biol Macromol. 2024 May;266(Pt 1):131012. doi: 10.1016/j.ijbiomac.2024.131012. Epub 2024 Mar 23. PMID: 38522709. 20: Cheng J, Wang X, Wang R, Sheng J, Guo S, Liu T, Wang Z. Effect of Zusanli Acupoint Injection with Anisodamine on Postoperative Recovery Quality of Patients Undergoing Bariatric Surgery. Obes Surg. 2024 May;34(5):1717-1725. doi: 10.1007/s11695-024-07182-9. Epub 2024 Mar 20. PMID: 38507149; PMCID: PMC11031441.