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1-Aminocyclobutanecarboxylic acid

1-Aminocyclobutanecarboxylic acid is a partial NMDA receptor agonist (activator) acting on the NR1 glycine site.
1-Aminocyclobutanecarboxylic acid
1-Aminocyclobutanecarboxylic acid Chemical Structure CAS No.: 22264-50-2
Product category: iGluR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
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Product Description
1-Aminocyclobutanecarboxylic acid is a partial NMDA receptor agonist (activator) acting on the NR1 glycine site.
1-Aminocyclobutanecarboxylic acid (ACBC) is a conformationally constrained cyclic amino acid that acts as a partial agonist at the NMDA (N-methyl-D-aspartic acid) receptor, specifically targeting the glycine modulatory site on the NR1 subunit. This compound is a structural analog of glycine where the amino and carboxyl groups are incorporated into a cyclobutane ring, restricting the conformational flexibility of the molecule. As a partial agonist at the glycine site of the NMDA receptor, 1-Aminocyclobutanecarboxylic acid can activate the receptor but with lower efficacy than the full agonist glycine. This unique pharmacological profile makes it a valuable tool for studying the structure-activity relationships of the NMDA receptor glycine site and for investigating the functional consequences of partial agonism at this receptor. The compound has a molecular weight of 115.13 g/mol and is supplied as a research reagent. It is not approved for human therapeutic use and is strictly for research purposes.
Biological Activity I Assay Protocols (From Reference)
Targets
NMDA (N-methyl-D-aspartic acid) receptor glycine modulatory site on the NR1 subunit. 1-Aminocyclobutanecarboxylic acid acts as a partial agonist at this site.
ln Vitro
1-Aminocyclobutanecarboxylic acid is a partial agonist at the NMDA receptor glycine site. As a partial agonist, it binds to the glycine modulatory site on the NR1 subunit and activates the receptor, but with lower efficacy compared to the full agonist glycine. This partial agonist activity allows the compound to act as both an agonist and an antagonist depending on the concentration of endogenous glycine present. In the presence of low glycine concentrations, it can potentiate NMDA receptor activity, while in the presence of high glycine concentrations, it can act as a competitive antagonist by occupying the binding site and preventing full activation.
ln Vivo
No detailed in vivo activity data are publicly available for 1-Aminocyclobutanecarboxylic acid. As an NMDA receptor glycine site partial agonist, its in vivo effects would be expected to be related to modulation of NMDA receptor-mediated glutamatergic neurotransmission. The compound's partial agonist activity suggests that it may have a more favorable safety profile compared to full agonists, as it would not produce maximal receptor activation even at high concentrations.
Enzyme Assay
In vitro receptor binding assays for 1-Aminocyclobutanecarboxylic acid are performed to evaluate its affinity for the NMDA receptor glycine site. Radioligand binding studies using membrane preparations from brain tissue or cells expressing NMDA receptors are conducted. The compound's ability to displace a specific radiolabeled glycine site ligand, such as [3H]-MDL-105,519 or [3H]-glycine, is measured to calculate its binding affinity. Functional assays, such as measuring NMDA receptor-mediated calcium influx or electrophysiological recordings, are used to confirm its partial agonist activity.
Cell Assay
In vitro cell-based assays are conducted using cells expressing recombinant NMDA receptors (e.g., HEK-293 cells co-transfected with NR1 and NR2 subunits). The cells are treated with 1-Aminocyclobutanecarboxylic acid, and receptor activation is measured by assessing downstream signaling events such as calcium mobilization or electrophysiological responses. The partial agonist activity is characterized by comparing the maximal response elicited by the compound to that of the full agonist glycine.
Animal Protocol
In vivo studies would be conducted in animal models to evaluate the effects of 1-Aminocyclobutanecarboxylic acid on NMDA receptor-mediated processes. The compound could be administered via various routes, and its effects on learning and memory, seizure susceptibility, and neuroprotection could be assessed. However, no specific in vivo data are publicly available for this compound.
ADME/Pharmacokinetics
No detailed pharmacokinetic data are publicly available for 1-Aminocyclobutanecarboxylic acid. As a small, polar amino acid analog, its oral bioavailability is likely limited, and it may not readily cross the blood-brain barrier. The compound's pharmacokinetic properties would be studied in preclinical models to guide in vivo experiments if needed.
Toxicity/Toxicokinetics
No specific toxicity data are publicly available for 1-Aminocyclobutanecarboxylic acid. As an NMDA receptor modulator, its toxicity profile would be expected to be related to its mechanism of action. Excessive NMDA receptor activation can lead to excitotoxicity, while excessive inhibition can impair synaptic plasticity and cognitive function.
References

[1]. Mechanism of partial agonist action at the NR1 subunit of NMDA receptors. Neuron. 2005 Jul 7;47(1):71-84.

Additional Infomation
1-Aminocyclobutanecarboxylic acid is an L-α-amino acid.
1-Aminocyclobutanecarboxylic acid is a conformationally constrained cyclic amino acid that acts as a partial agonist at the NMDA receptor glycine site. It is used as a research tool to study the structure-activity relationships of the NMDA receptor glycine site and the functional consequences of partial agonism. The compound is not approved for human therapeutic use and is strictly for research purposes. It is also known as ACBC and has the CAS number 22264-50-2.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H9NO2
Molecular Weight
115.13
Exact Mass
115.063
CAS #
22264-50-2
PubChem CID
89643
Appearance
Off-white to gray solid powder
Density
1.3±0.1 g/cm3
Boiling Point
241.1±23.0 °C at 760 mmHg
Melting Point
261ºC (dec.)
Flash Point
99.6±22.6 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.540
LogP
-0.62
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
8
Complexity
118
Defined Atom Stereocenter Count
0
SMILES
C1CC(C1)(C(=O)O)N
InChi Key
FVTVMQPGKVHSEY-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H9NO2/c6-5(4(7)8)2-1-3-5/h1-3,6H2,(H,7,8)
Chemical Name
1-aminocyclobutane-1-carboxylic acid
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.
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)
H2O: 27.78 mg/mL (241.29 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 33.33 mg/mL (289.50 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 8.6858 mL 43.4292 mL 86.8583 mL
5 mM 1.7372 mL 8.6858 mL 17.3717 mL
10 mM 0.8686 mL 4.3429 mL 8.6858 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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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.
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