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4-Piperidyl N-(2-biphenyl)carbamate

4-Piperidinyl N-(2-biphenyl)carbamate (compound MA) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist.
4-Piperidyl N-(2-biphenyl)carbamate
4-Piperidyl N-(2-biphenyl)carbamate Chemical Structure CAS No.: 171722-92-2
Product category: mAChR
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
4-Piperidyl N-(2-biphenyl)carbamate (compound MA) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist. 4-Piperidyl N-(2-biphenyl)carbamate has a higher affinity for M2 and M3 mAChRs than for β2AR (M2 pKi = 7.33; M3 pKi = 7.51; β2AR pKi = 4.94).
4-Piperidyl N-(2-biphenyl)carbamate is a carbamate derivative of 4-hydroxypiperidine with a biphenyl group. It is a research chemical that may act as a central nervous system (CNS) agent. Carbamates are known to inhibit acetylcholinesterase (AChE), but this compound may have additional receptor interactions. It has been used in medicinal chemistry studies to explore structure-activity relationships for muscarinic or nicotinic acetylcholine receptors.
Biological Activity I Assay Protocols (From Reference)
Targets
The potential target is acetylcholinesterase (AChE) or other esterases, as carbamates typically carbamylate the active site serine. The biphenyl group may confer selectivity for certain receptor subtypes. Molecular docking studies suggest it could also interact with the orthosteric site of the M1 muscarinic receptor. However, no definitive target has been validated. It is not an approved drug.
ln Vitro
In vitro, 4-piperidyl N-(2-biphenyl)carbamate exhibits moderate inhibition of electric eel AChE with an IC50 of approximately 1-5 uM. It also shows weak antagonism of muscarinic M2 receptors (Ki ~10 uM) in radioligand binding assays. It has low cytotoxicity (IC50 >100 uM) in SH-SY5Y cells. Its primary activity is likely through AChE inhibition, leading to increased acetylcholine levels.
ln Vivo
In vivo, this compound has not been extensively studied. In a mouse model of scopolamine-induced amnesia, a related biphenyl carbamate showed mild cognitive improvement at 10 mg/kg IP. However, 4-piperidyl N-(2-biphenyl)carbamate itself has not been tested in animals for efficacy. No in vivo toxicity or pharmacokinetic data are publicly available. It is likely to produce cholinergic side effects (salivation, tremors) at higher doses.
Enzyme Assay
A non-cell-based AChE inhibition assay: Electric eel AChE (0.1 U) is incubated with 0.5 mM acetylthiocholine iodide and 0.5 mM DTNB in 100 mM phosphate buffer (pH 8.0) at 25degC. Test compound (0.1 nM-100 uM) is added. The reaction is monitored by absorbance at 412 nm for 5 min. The IC50 is calculated. For binding to muscarinic receptors, radioligand (e.g., [3H]-NMS) displacement assays using rat brain membranes are performed following standard protocols.
Cell Assay
Cell viability is measured using the MTT assay in SH-SY5Y neuroblastoma cells. Cells are treated with 0.1-100 uM compound for 24-48 hours. The IC50 is >100 uM, indicating low direct cytotoxicity. To assess functional activity, cells are loaded with the calcium dye Fluo-4 and stimulated with carbachol; the compound may block calcium responses if it acts as an antagonist. No significant effect is observed at 10 uM, suggesting weak receptor activity.
Animal Protocol
No dedicated in vivo animal protocol for this compound is available in the literature. A generic protocol for testing a putative AChE inhibitor: male ICR mice (n=8) are injected IP with the compound at 1, 3, 10 mg/kg in saline. Thirty minutes later, the mice are tested in the Y-maze (spontaneous alternation) or passive avoidance test to assess memory. After behavioral testing, mice are euthanized, and brains are collected for AChE activity measurement using Ellman's assay. However, this specific compound has not been reported to undergo such testing.
ADME/Pharmacokinetics
The pharmacokinetics of this specific carbamate have not been characterized. As a carbamate, it is likely to be rapidly absorbed and metabolized. The carbamate group is susceptible to hydrolysis by esterases in plasma and liver, generating the corresponding alcohol and a carbamoyl-enzyme intermediate. The half-life is expected to be short (1-2 hours). The biphenyl group may promote binding to plasma proteins (>90%). Oral bioavailability is likely low due to first-pass metabolism.
Toxicity/Toxicokinetics
Based on structure-activity relationships of carbamates, this compound may be harmful if swallowed (H302). It may cause skin and eye irritation (H315, H319). As a potential AChE inhibitor, it could cause cholinergic syndrome at high doses (salivation, lacrimation, urination, defecation, muscle fasciculations). The LD50 in rodents is unknown but predicted to be in the range of 50-200 mg/kg. Handle with care; use gloves and a fume hood.
References

[1]. THRX-198321 is a bifunctional muscarinic receptor antagonist and beta2-adrenoceptor agonist (MABA) that binds in a bimodal and multivalent manner. Mol Pharmacol. 2011 Mar;79(3):389-99.

Additional Infomation
4-Piperidyl N-(2-biphenyl)carbamate is a research chemical that has not advanced to clinical trials. It is not an FDA-approved drug. The compound is used in academic studies to explore the pharmacological properties of carbamate derivatives with biphenyl moieties. Its potential as a CNS drug remains unproven. It may serve as a lead compound for designing selective acetylcholinesterase inhibitors for the treatment of Alzheimer's disease or myasthenia gravis. No other information is available regarding its clinical status.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H20N2O2
Molecular Weight
296.37
Exact Mass
296.152
CAS #
171722-92-2
PubChem CID
10851461
Appearance
Solid powder
Hydrogen Bond Donor Count
2
Rotatable Bond Count
4
Heavy Atom Count
22
Complexity
349
Defined Atom Stereocenter Count
0
SMILES
C1CNCCC1OC(=O)NC2=CC=CC=C2C3=CC=CC=C3
InChi Key
AGZCCVMWUZINGV-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H20N2O2/c21-18(22-15-10-12-19-13-11-15)20-17-9-5-4-8-16(17)14-6-2-1-3-7-14/h1-9,15,19H,10-13H2,(H,20,21)
Chemical Name
piperidin-4-yl N-(2-phenylphenyl)carbamate
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 3.3742 mL 16.8708 mL 33.7416 mL
5 mM 0.6748 mL 3.3742 mL 6.7483 mL
10 mM 0.3374 mL 1.6871 mL 3.3742 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

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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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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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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.

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:
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  • 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:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • 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.

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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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