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Anisodamine hydrobromide

Cat No.:V30160 Purity: ≥98%
Anisodamine HBr (6-Hydroxyhyoscyamine HBr), a belladonna alkaloid, is also a non-subtype selective muscarinic and nicotinic cholinoceptor antagonist.
Anisodamine hydrobromide
Anisodamine hydrobromide Chemical Structure CAS No.: 55449-49-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
100mg
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Other Forms of Anisodamine hydrobromide:

  • Anisodamine
  • Anisodamine hydrochloride (6-Hydroxyhyoscyamine hydrochloride)
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Top Publications Citing lnvivochem Products
Product Description
Anisodamine HBr (6-Hydroxyhyoscyamine HBr), a belladonna alkaloid, is also a non-subtype selective muscarinic and nicotinic cholinoceptor antagonist. Anisodamine HBr has antioxidant and anti~inflammatory activities.
Anisodamine hydrobromide (CAS#: 55449-49-5), also known as 6-Hydroxyhyoscyamine hydrobromide, is a belladonna alkaloid and a non-subtype-selective muscarinic and nicotinic cholinoceptor antagonist. The compound shows antioxidant and anti-inflammatory properties. It is used in the treatment of septic shock, circulatory disorders, and gastrointestinal colic. It also exhibits protective effects against ischemia-reperfusion injury and oxidative stress. Its molecular formula is C17H23NO4·HBr with a molecular weight of 386.28 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Anisodamine hydrobromide targets muscarinic acetylcholine receptors (mAChR) and nicotinic cholinoceptors. It is a non-subtype-selective muscarinic antagonist. The compound also acts as an α1-adrenergic receptor antagonist. Its mechanism involves inhibiting muscarinic receptors, which increases the amount of endogenous ACh that binds to α-7nAChR. Anisodamine hydrobromide shows antioxidant and anti-inflammatory properties.
ln Vitro
When anisodamine hydrobromide (100 μg/mL) was pretreated for 20 minutes with RAW264.7 cells, the mean fluorescence intensity of α-bungarotoxin binding was significantly lower than when Ach was used alone. [2]. Anisodamine hydrobromide may work by inhibiting muscarinic receptors, which in turn increases the amount of endogenous ACh that binds to α-7nAChR [2].
In vitro, Anisodamine hydrobromide is a non-subtype-selective muscarinic and nicotinic cholinoceptor antagonist. It shows antioxidant and anti-inflammatory properties. The compound inhibits muscarinic receptors, increasing endogenous ACh binding to α-7nAChR. Its receptor binding and functional antagonism have been characterized in various in vitro systems. Anisodamine hydrobromide is a belladonna alkaloid.
ln Vivo
Mortality is dramatically reduced to 20% with anisodamine hydrobromide (50 mg/kg; intraperitoneal injection; 72 hours) [2].
In vivo, Anisodamine hydrobromide is used in the treatment of septic shock, circulatory disorders, and gastrointestinal colic. It exhibits protective effects against ischemia-reperfusion injury and oxidative stress. The compound is a naturally occurring atropine derivative used in China for treating acute circulatory shock. It acts as an anticholinergic and α1-adrenergic receptor antagonist. Further in vivo studies have evaluated its therapeutic applications.
Enzyme Assay
In vitro receptor binding assays for Anisodamine hydrobromide involve measuring affinity for muscarinic acetylcholine receptors (mAChR) and nicotinic cholinoceptors. Radioligand binding displacement studies are performed using membranes from cells expressing recombinant receptors. Functional antagonism is assessed by measuring inhibition of acetylcholine-induced signaling. Antioxidant activity is assessed by measuring free radical scavenging using DPPH or other assays. Anti-inflammatory activity is assessed by measuring inhibition of pro-inflammatory cytokine production. Assays are performed in appropriate buffer systems with positive controls.
Cell Assay
In vitro cell-based assays for Anisodamine hydrobromide are conducted in various cell lines. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Receptor antagonism is assessed by measuring inhibition of acetylcholine-induced calcium mobilization or other signaling. Antioxidant activity is assessed by measuring intracellular ROS levels. Anti-inflammatory activity is assessed by measuring cytokine levels by ELISA. Cell viability is assessed by standard assays. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Animal/Disease Models: LPS-induced shock mice [2]
Doses: 50 mg/kg
Route of Administration: intraperitoneal (ip) injection
Experimental Results: The mortality rate was Dramatically diminished to 20%.
Anisodamine hydrobromide in vivo studies are conducted in animal models of septic shock, circulatory disorders, and ischemia-reperfusion injury. Animals are treated with Anisodamine hydrobromide via injection. For septic shock studies, animals are subjected to LPS or cecal ligation and puncture. Hemodynamic parameters and survival are monitored. For ischemia-reperfusion studies, organ injury and oxidative stress markers are assessed. For gastrointestinal colic studies, gastrointestinal motility is assessed. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biochemical analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
Anisodamine hydrobromide (MW 386.28 g/mol) is a belladonna alkaloid and muscarinic and nicotinic cholinoceptor antagonist. It is also known as 6-Hydroxyhyoscyamine hydrobromide. The compound is soluble in water and DMSO. It is stable under recommended storage conditions. Anisodamine hydrobromide is used in the treatment of septic shock and circulatory disorders. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution have been characterized in preclinical and clinical studies.
Toxicity/Toxicokinetics
Anisodamine hydrobromide is generally well-tolerated at therapeutic doses. The compound is a belladonna alkaloid with established safety profiles. It shows antioxidant and anti-inflammatory properties. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation is available from clinical use data.
References

[1]. Eisenkraft A. Possible role for anisodamine in organophosphate poisoning. Br J Pharmacol. 2016;173(11):1719-1727.

[2]. Antishock effect of anisodamine involves a novel pathway for activating alpha7 nicotinic acetylcholine receptor. Crit Care Med. 2009;37(2):634-641.

Additional Infomation
Anisodamine hydrobromide (6-Hydroxyhyoscyamine hydrobromide) is a belladonna alkaloid and non-subtype-selective muscarinic and nicotinic cholinoceptor antagonist. It shows antioxidant and anti-inflammatory properties. The compound is used in the treatment of septic shock, circulatory disorders, and gastrointestinal colic. It exhibits protective effects against ischemia-reperfusion injury and oxidative stress. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H23NO4
Molecular Weight
305.36882
Exact Mass
385.089
CAS #
55449-49-5
Related CAS #
Anisodamine;55869-99-3;Anisodamine hydrochloride;131674-05-0
PubChem CID
118856046
Appearance
White to off-white solid powder
LogP
1.797
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Heavy Atom Count
23
Complexity
396
Defined Atom Stereocenter Count
5
SMILES
CN1[C@H]2C[C@@H](C[C@@H]1[C@H](C2)O)OC(=O)[C@H](CO)C3=CC=CC=C3.Br
InChi Key
KMYQCELRVANQNG-YXGOVGSCSA-N
InChi Code
InChI=1S/C17H23NO4.BrH/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;1H/t12-,13-,14+,15+,16-;/m0./s1
Chemical Name
[(1R,3S,5R,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate;hydrobromide
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~258.88 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (5.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2747 mL 16.3736 mL 32.7472 mL
5 mM 0.6549 mL 3.2747 mL 6.5494 mL
10 mM 0.3275 mL 1.6374 mL 3.2747 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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