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O-Acetylgalanthamine

Cat No.:V46662 Purity: ≥98%
O-Acetylgalanthamine is an acetylated alkaloid, a naturally occurring compound extracted from Narcissus pseudonarcissus.
O-Acetylgalanthamine
O-Acetylgalanthamine Chemical Structure CAS No.: 25650-83-3
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
O-Acetylgalanthamine is an acetylated alkaloid, a naturally occurring compound extracted from Narcissus pseudonarcissus.
O-Acetylgalanthamine (CAS 25650-83-3, O-AGLA) is an acetylated alkaloid, a naturally occurring compound extracted from the bulbs of Narcissus pseudonarcissus (Amaryllidaceae family). It has a molecular formula of C19H23NO4 and a molecular weight of 329.39. It is a derivative of galanthamine, a well-known acetylcholinesterase inhibitor used in the treatment of Alzheimer's disease. O-Acetylgalanthamine is used as a pharmaceutical standard and research chemical.
Biological Activity I Assay Protocols (From Reference)
Targets
O-Acetylgalanthamine is a derivative of galanthamine, which targets acetylcholinesterase (AChE), the enzyme responsible for the breakdown of acetylcholine in the synaptic cleft. By inhibiting AChE, galanthamine increases acetylcholine levels and enhances cholinergic neurotransmission. O-Acetylgalanthamine is expected to have similar activity, though the acetyl group may alter its potency and pharmacokinetic properties. As a natural product, it may also interact with other targets such as nicotinic receptors.
ln Vitro
In vitro, O-Acetylgalanthamine is a natural alkaloid with potential acetylcholinesterase inhibitory activity, similar to galanthamine. However, specific IC50 values and detailed in vitro activity data for O-Acetylgalanthamine are not extensively reported in the available literature. The compound is primarily used as a reference standard and research chemical for studying galanthamine derivatives and their biological activities.
ln Vivo
In vivo, O-Acetylgalanthamine is expected to show acetylcholinesterase inhibitory activity and potential cognitive-enhancing effects, similar to galanthamine. However, specific in vivo efficacy data for O-Acetylgalanthamine are not extensively reported. The compound is primarily used as a pharmaceutical reference standard and research chemical, and it is not approved for clinical use.
Enzyme Assay
There are no specific in vitro enzyme/receptor binding assays for O-Acetylgalanthamine as a drug target. As an acetylcholinesterase inhibitor, it may be studied in AChE activity assays using Ellman's method. The compound is incubated with AChE enzyme and the substrate acetylthiocholine, and the production of thiocholine is measured spectrophotometrically at 412 nm. The IC50 is determined from dose-response curves. However, detailed protocols for this specific compound are not extensively reported.
Cell Assay
There are no specific in vitro cellular assays for O-Acetylgalanthamine as a pharmacologically active compound. As an AChE inhibitor, it can be tested in neuronal cell cultures or neuroblastoma cell lines expressing AChE. Cells are treated with various concentrations of the compound (typically 1-100 μM) for 1-24 hours, and AChE activity is measured in cell lysates. Cell viability is assessed using MTT assays. However, detailed protocols for this specific compound are not extensively reported.
Animal Protocol
There are no specific in vivo animal studies for O-Acetylgalanthamine as a pharmacologically active compound. As a galanthamine derivative, it may be studied in rodent models of cognitive impairment (e.g., scopolamine-induced amnesia). The compound would be administered orally or intraperitoneally, and cognitive function would be assessed using Morris water maze or novel object recognition tests. However, specific protocols for this compound are not extensively reported.
ADME/Pharmacokinetics
Pharmacokinetic properties of O-Acetylgalanthamine are not extensively reported. The compound has a molecular weight of 329.39 and is expected to have moderate lipophilicity. As an acetylated derivative of galanthamine, it may have different pharmacokinetic properties compared to the parent compound, including altered absorption, distribution, metabolism, and excretion. Specific PK parameters are not detailed.
Toxicity/Toxicokinetics
The toxicity profile of O-Acetylgalanthamine is not extensively reported. As a galanthamine derivative, it may have similar toxicity to galanthamine, including gastrointestinal and neurological effects at high doses. The compound is for research use only and not for human therapeutic use. Standard toxicity studies would include acute toxicity in rodents and cytotoxicity assays in neuronal cell lines. No specific genotoxicity data are reported.
Additional Infomation
Reports indicate that daffodils (Narcissus pseudonarcissus) contain O-acetylgalantamine, and relevant data is available for reference.
O-Acetylgalanthamine (CAS 25650-83-3, O-AGLA) is an acetylated alkaloid derived from Narcissus pseudonarcissus, and a derivative of the acetylcholinesterase inhibitor galanthamine. It has a molecular formula of C19H23NO4 and a molecular weight of 329.39. The compound is used as a pharmaceutical reference standard and research chemical. It is not approved for clinical use and is available for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H23NO4
Molecular Weight
329.39
Exact Mass
329.163
CAS #
25650-83-3
PubChem CID
10131512
Appearance
Typically exists as solid at room temperature
LogP
2.359
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
24
Complexity
536
Defined Atom Stereocenter Count
3
SMILES
O=C(O[C@H]1/C=C\[C@@]24c3c(O[C@H]2C1)c(OC)ccc3CN(C)CC4)C
InChi Key
ZTWNMOVEDXUICV-QOKNQOGYSA-N
InChi Code
InChI=1S/C19H23NO4/c1-12(21)23-14-6-7-19-8-9-20(2)11-13-4-5-15(22-3)18(17(13)19)24-16(19)10-14/h4-7,14,16H,8-11H2,1-3H3/t14-,16-,19-/m0/s1
Chemical Name
[(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] acetate
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 3.0359 mL 15.1796 mL 30.3591 mL
5 mM 0.6072 mL 3.0359 mL 6.0718 mL
10 mM 0.3036 mL 1.5180 mL 3.0359 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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