D-AP5
D-AP5 (CAS: 79055-68-8) is a selective antagonist of the NMDA receptor. It competitively inhibits glutamate binding at the NMDA receptor site, exhibiting an affinity constant (Kd) of approximately 1.4 μM. In animal research, administration of D-AP5 leads to impairment in spatial learning tasks, specifically causing deficits in sensorimotor function and spatial memory performance. Due to its targeted action on NMDA receptors, D-AP5 serves as an important pharmacological tool for studying glutamate-related synaptic plasticity, learning, and memory mechanisms.
| Physical Appearance | A crystalline solid |
| Storage | Store at -20°C |
| M.Wt | 197.13 |
| Cas No. | 79055-68-8 |
| Formula | C5H12NO5P |
| Solubility | insoluble in DMSO; insoluble in EtOH; ≥28.1 mg/mL in H2O |
| Chemical Name | (R)-2-amino-5-phosphonopentanoic acid |
| SDF | Download SDF |
| Canonical SMILES | OP(O)(CCC[C@H](C(O)=O)N)=O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
Neonatal slices, juvenile slices |
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Preparation method |
Soluble to 100 mM in sterile water. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
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Reacting condition |
100 μM |
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Applications |
In neonatal slices, a 5 Hz/3 min train of stimuli did not induce LTD of field EPSPs in the presence of 100 μM D-AP5. In juvenile slices, a 5 Hz/3 min train of stimuli did not induce LTD of field EPSPs in the presence of 100 μM D-AP5. In the presence of 100 μM D-AP5, voltage-clamping the cells at -80 mV during the induction protocol prevented the induction of mGluR-LTD. |
| Animal experiment [2,3]: | |
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Animal models |
Rats |
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Dosage form |
0–50 mM |
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Application |
In rats, D-AP5 (0–50 mM) via osmotic minipumps impaired spatial learning in a linear dose-dependent manner, highly correlated with its corresponding impairment of hippocampal LTP. No concentration of D-AP5 was observed to block LTP without affecting learning. Acute intrahippocampal infusion of radiolabelled D-AP5 revealed relatively restricted diffusion and was used to estimate whole-tissue hippocampal drug concentrations. Chronic i.c.v. infusions of D-AP5 caused a delay-dependent impairment of memory. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Oliet S H R, Malenka R C, Nicoll R A. Two distinct forms of long-term depression coexist in CA1 hippocampal pyramidal cells[J]. Neuron, 1997, 18(6): 969-982. [2]. Davis S, Butcher S P, Morris R G. The NMDA receptor antagonist D-2-amino-5-phosphonopentanoate (D-AP5) impairs spatial learning and LTP in vivo at intracerebral concentrations comparable to those that block LTP in vitro[J]. Journal of Neuroscience, 1992, 12(1): 21-34. [3]. Steele R J, Morris R G M. Delay‐dependent impairment of a matching‐to‐place task with chronic and intrahippocampal infusion of the NMDA‐antagonist D‐AP5[J]. Hippocampus, 1999, 9(2): 118-136. | |
Quality Control & MSDS
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Chemical structure
