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N-Methylmoranoline

Cat No.:V29595 Purity: ≥98%
N-Methylmoranoline (MOR 14) is an inhibitor (blocker/antagonist) of α-glucosidase.
N-Methylmoranoline
N-Methylmoranoline Chemical Structure CAS No.: 69567-10-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-Methylmoranoline (MOR 14) is an inhibitor (blocker/antagonist) of α-glucosidase.
N-Methylmoranoline (CAS 69567-10-8), also known as MOR 14 or N-Methyl-1-deoxynojirimycin, is a potent and specific inhibitor of α-glucosidases. With a molecular formula of C₇H₁₅NO₄ and a molecular weight of 177.20 g/mol, it is a naturally occurring or synthetic pyrroloquinoline-type alkaloid derivative. This compound is widely used in biochemical and metabolic research to study glycan biosynthesis and glycoprotein processing. As an α-glucosidase inhibitor, it prevents the cleavage of glucose from glycoproteins, which is a critical step in the maturation of glycoproteins in the endoplasmic reticulum. It is associated with the nervous system and used as a research tool in neurotransmitter receptor modulation and neural signaling studies.
Biological Activity I Assay Protocols (From Reference)
Targets
N-Methylmoranoline targets α-glucosidases, which are enzymes that hydrolyze the terminal, non-reducing (1→4)-linked α-D-glucose residues with the release of α-D-glucose. It is a potent inhibitor of these enzymes, with specific activity against rabbit intestinal sucrase (IC₅₀ = 0.068 µg/ml) and maltase (IC₅₀ = 0.46 µg/ml). By inhibiting these enzymes, it interferes with the processing of N-linked glycoproteins, which can have downstream effects on protein folding, trafficking, and function. This mechanism makes it a valuable tool for studying the role of glycosylation in various cellular processes.
ln Vitro
N-methylmorpholine dose-dependently decreases α-1,6-glucosidase activity in rabbit heart extracts. Considerable levels of N-methylmorpholine taken up by the myocardium are sufficient to totally block α-1,6-glucosidase. Preischemic therapy with 25, 50, and 100 mg/kg N-methylmorpholine dose-dependently lowers infarct size without affecting blood pressure or heart rate [1]. MOR-14 significantly raised PKC-ε levels in the granular fraction after 20 and 30 minutes of ischemia and in the cytosolic fraction at 30 minutes of ischemia [2].
In vitro studies have shown that N-Methylmoranoline is a potent inhibitor of α-glucosidases. It dose-dependently decreases the α-1,6-glucosidase activity in rabbit heart extract. It specifically inhibits rabbit intestinal sucrase and maltase with IC₅₀ values of 0.068 and 0.46 µg/ml, respectively. The compound's ability to inhibit glycoprotein processing in vitro makes it a key tool for studying the role of glycosylation in protein function, viral entry, and various diseases. Its activity is primarily measured by its ability to prevent the enzymatic cleavage of synthetic or natural substrates.
ln Vivo
After 10 and 30 minutes of ischemia, N-methylmorpholine decreases lactate buildup, glycogenolysis, and α-1,6-glucosidase activity to about 20% [1]. MOR-14 inhibits glycogenolysis in isolated rat hearts, preventing post-ischemic left ventricular failure [3].
In vivo, N-Methylmoranoline is studied for its effects on glycoprotein processing and its potential therapeutic applications. By inhibiting α-glucosidases, it can alter the glycosylation of proteins, which may have implications for viral infections (as some viruses require proper glycosylation for entry), cancer metastasis, and lysosomal storage disorders. It is used in animal models to investigate the role of glycosylation in disease pathology. The compound's ability to modulate the nervous system is also explored, given its association with neurotransmitter receptor studies.
Enzyme Assay
In vitro enzyme assays for N-Methylmoranoline typically involve incubating the compound with α-glucosidase enzymes (such as sucrase or maltase) and a chromogenic or fluorogenic substrate. The enzyme's activity is measured by the rate of substrate cleavage, and the compound's inhibitory effect is determined by comparing the activity in the presence and absence of the inhibitor. IC₅₀ values are calculated from dose-response curves. These assays are essential for characterizing the potency and selectivity of the compound against different α-glucosidases.
Cell Assay
In vitro cell-based assays for N-Methylmoranoline use cell lines to study the effects of α-glucosidase inhibition on glycoprotein processing. Cells are treated with the compound, and the glycosylation status of specific proteins is analyzed by gel electrophoresis or lectin-binding assays. The compound's effects on cell viability, protein trafficking, and viral entry can also be assessed. These studies help to elucidate the cellular consequences of inhibiting glycoprotein maturation.
Animal Protocol
In vivo animal studies for N-Methylmoranoline typically involve administering the compound to animal models to study its effects on glycoprotein processing and disease pathology. For example, it may be used in models of viral infection to assess its ability to inhibit viral replication by altering the glycosylation of viral envelope proteins. In metabolic studies, its effects on glucose homeostasis can be evaluated. Pharmacokinetic and toxicological studies are also performed to assess its suitability as a drug candidate.
ADME/Pharmacokinetics
N-Methylmoranoline has a molecular weight of 177.20 g/mol and a molecular formula of C₇H₁₅NO₄. It is a solid powder. It is soluble in water and organic solvents. As a small molecule with moderate polarity, it is expected to have reasonable oral bioavailability. It should be stored desiccated at -20°C for long-term stability. Detailed pharmacokinetic parameters such as half-life and volume of distribution are not widely published but are determined in preclinical studies.
Toxicity/Toxicokinetics
The toxicity profile of N-Methylmoranoline is not extensively detailed in public literature, but as a research compound, it is considered to have a manageable safety profile for in vitro and preclinical use. Like other iminosugars, it may cause gastrointestinal side effects at high doses due to its inhibition of intestinal glucosidases. Standard laboratory safety precautions should be followed when handling the compound. It is not intended for human therapeutic use without further development and regulatory approval.
References

[1]. N-methyl-1-deoxynojirimycin (MOR-14), an alpha-glucosidase inhibitor, markedly reduced infarct size in rabbit hearts. Circulation. 1998 Apr 7;97(13):1290-7.

[2]. Role of protein kinase C in the reduction of infarct size by N-methyl-1-deoxynojirimycin, an alpha-1,6-glucosidase inhibitor. Br J Pharmacol. 2001 Jul;133(5):635-42.

[3]. N-methyl-1-deoxynojirimycin (MOR-14), an alpha-glucosidase inhibitor, markedly improves postischemic left ventricular dysfunction. Heart Vessels. 2000;15(6):268-73.

Additional Infomation
N-methyldeoxynojirimycin has been reported to have been found in mulberry trees, Homo sapiens, and other organisms with available data.
N-Methylmoranoline (MOR 14) is a potent α-glucosidase inhibitor used as a research tool to study glycoprotein processing and glycan biosynthesis. It is also known as N-Methyl-1-deoxynojirimycin. The compound is used in studies related to viral entry, cancer metastasis, and lysosomal storage disorders. It is associated with the nervous system and used in neurotransmitter receptor modulation research. It is not approved for clinical use and is intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H15NO4
Molecular Weight
177.1983
Exact Mass
177.1
CAS #
69567-10-8
PubChem CID
92381
Appearance
White to off-white solid powder
Density
1.394g/cm3
Boiling Point
367.2ºC at 760 mmHg
Melting Point
126-128ºC
Flash Point
220.3ºC
Index of Refraction
1.58
LogP
-1.9
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Heavy Atom Count
12
Complexity
154
Defined Atom Stereocenter Count
4
SMILES
CN1C[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
InChi Key
AAKDPDFZMNYDLR-XZBKPIIZSA-N
InChi Code
InChI=1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3/t4-,5+,6-,7-/m1/s1
Chemical Name
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
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 5.6433 mL 28.2167 mL 56.4334 mL
5 mM 1.1287 mL 5.6433 mL 11.2867 mL
10 mM 0.5643 mL 2.8217 mL 5.6433 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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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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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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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)
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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