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Galanthamine N-Oxide

Cat No.:V21478 Purity: ≥98%
Galanthamine N-Oxide is an alkaloid extracted from the bulbs of Zephyranthes concolor.
Galanthamine N-Oxide
Galanthamine N-Oxide Chemical Structure CAS No.: 134332-50-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
Galanthamine N-Oxide is an alkaloid extracted from the bulbs of Zephyranthes concolor. Galanthamine N-Oxide inhibits electric eel acetylcholinesterase (AChE) with EC50 of 26.2 μM. Galanthamine N-Oxide is a significant inhibitor of substrate regulation in the active site of TcAChE, hAChE and hBChE enzymes.
Galanthamine N-Oxide (CAS#: 134332-50-6, molecular weight 303.35, molecular formula C17H21NO4) is a naturally occurring alkaloid and a derivative of galanthamine. It is a metabolite of galanthamine, an acetylcholinesterase inhibitor used in the treatment of Alzheimer's disease. Galanthamine N-oxide has been studied for its biological activities, including its effects on the cholinergic system. It is a research compound used to study the metabolism and pharmacology of galanthamine. The compound is also known as galanthamine-N-oxide.
Biological Activity I Assay Protocols (From Reference)
Targets
Galanthamine N-oxide targets acetylcholinesterase, the enzyme responsible for the breakdown of acetylcholine. As an N-oxide derivative of galanthamine, it may have reduced activity compared to the parent compound. Its effects on the cholinergic system are related to its ability to inhibit acetylcholinesterase. The compound's specific binding affinity and inhibitory potency have been characterized in biochemical assays. It is a metabolite of galanthamine.
ln Vitro
In vitro, galanthamine N-oxide has been studied for its effects on acetylcholinesterase activity. Its inhibitory potency has been compared to that of galanthamine. The compound's activity may be lower than the parent compound due to the N-oxide modification. Its effects on neuronal cells and cholinergic signaling have been studied. Its role as a metabolite has been characterized in various in vitro systems.
ln Vivo
In vivo, galanthamine N-oxide is a metabolite of galanthamine. It is formed through the oxidation of galanthamine in the body. Its presence in biological fluids reflects the metabolism of galanthamine. Its pharmacological activity in vivo is related to its ability to inhibit acetylcholinesterase, although its potency may be reduced compared to galanthamine. Its role in the therapeutic effects of galanthamine is not fully understood.
Enzyme Assay
In vitro enzyme assays for galanthamine N-oxide involve measuring the inhibition of acetylcholinesterase activity using purified enzyme preparations. The compound is incubated with acetylcholinesterase and a chromogenic substrate, and the rate of substrate hydrolysis is measured spectrophotometrically. The IC50 value is determined from dose-response curves. Its activity is compared to that of galanthamine.
Cell Assay
In vitro cell-based assays for galanthamine N-oxide involve treating neuronal cells with the compound to assess its effects on cholinergic signaling. Acetylcholine levels in cell lysates or culture media are measured. The compound's effects on cell viability and function are also assessed. These assays characterize its biological activity and compare it to galanthamine.
Animal Protocol
In vivo animal experiments for galanthamine N-oxide have been conducted to study its metabolism and pharmacokinetics. Animals are administered galanthamine, and the formation of galanthamine N-oxide is measured in plasma and tissues. Its effects on acetylcholinesterase activity and cholinergic function in the brain are assessed. These studies have contributed to the understanding of galanthamine metabolism.
ADME/Pharmacokinetics
Metabolism / Metabolites
Galantamine N-oxide is a known human metabolite of galantamine.
Galanthamine N-oxide has a molecular weight of 303.35 and a molecular formula of C17H21NO4. It is a naturally occurring alkaloid and a metabolite of galanthamine. The compound is typically stored under recommended conditions for research compounds. Its physical and chemical properties are consistent with galanthamine derivatives. It is a research compound used in pharmacological studies.
Toxicity/Toxicokinetics
Specific toxicity data for galanthamine N-oxide is not extensively reported. As a metabolite of galanthamine, its safety profile is related to the parent compound. Galanthamine is generally well-tolerated at therapeutic doses. The N-oxide derivative may have a different safety profile. Standard safety precautions should be taken when handling the compound.
References

[1]. Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor. Molecules. 2011 Nov 15;16(11):9520-33.

Additional Infomation
Galanthamine N-Oxide has been reported in Lycoris radiata, Lycoris radiata, and Lycoris rubrum, and data are available.
Galanthamine N-oxide is a naturally occurring alkaloid and a metabolite of galanthamine. It is a derivative of galanthamine, an acetylcholinesterase inhibitor used in Alzheimer's disease. The compound has been studied for its biological activities. Galanthamine N-oxide is a research compound used to study the metabolism and pharmacology of galanthamine.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H21NO4
Molecular Weight
303.35300
Exact Mass
303.147
CAS #
134332-50-6
PubChem CID
11748698
Appearance
White to off-white solid powder
Melting Point
246-247ºC
LogP
1.821
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
22
Complexity
483
Defined Atom Stereocenter Count
3
SMILES
C[N+]1(CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O)[O-]
InChi Key
LROQBKNDGTWXET-FVWDGWMTSA-N
InChi Code
InChI=1S/C17H21NO4/c1-18(20)8-7-17-6-5-12(19)9-14(17)22-16-13(21-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-,18?/m0/s1
Chemical Name
(1S,12S,14R)-9-methoxy-4-methyl-4-oxido-11-oxa-4-azoniatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
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 : ~6.25 mg/mL (~20.60 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2965 mL 16.4826 mL 32.9652 mL
5 mM 0.6593 mL 3.2965 mL 6.5930 mL
10 mM 0.3297 mL 1.6483 mL 3.2965 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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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

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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