Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C8H17N2O5P |
| Molecular Weight | 252.2047 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1CN(CCCP(O)(O)=O)CCN1
InChI
InChIKey=CUVGUPIVTLGRGI-UHFFFAOYSA-N
InChI=1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)
3-(2-Carboxypiperazin-4-yl)Propyl-1-Phosphonic acid (also known as CPP) is neuro active amino acid and antagonist of the N-methyl-D-aspartate receptor (NMDA). It has been studied in rat models for memory, learning, and pain. Although it did show some efficacy in reducing pain it also appears to significantly impair working memory.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2876749
Curator's Comment: Davies J, Evans RH, Herrling PL, Jones AW, Olverman HJ, Pook P, Watkins JC.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8159442 |
446.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8159442 |
Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Influence of pharmacological manipulations of NMDA and cholinergic receptors on working versus reference memory in a dual component odor span task. | 2016-06 |
|
| The NMDA antagonist 3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid (CPP) has antinociceptive effect after intrathecal injection in the rat. | 1994-01 |
|
| A comparison between the in vivo and in vitro activity of five potent and competitive NMDA antagonists. | 1988-11 |
|
| Action of 3-((+/-)-2-carboxypiperazin-4-yl)-propyl-1-phosphonic acid (CPP): a new and highly potent antagonist of N-methyl-D-aspartate receptors in the hippocampus. | 1986-09-10 |
|
| CPP, a new potent and selective NMDA antagonist. Depression of central neuron responses, affinity for [3H]D-AP5 binding sites on brain membranes and anticonvulsant activity. | 1986-09-10 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27194794
Adult Sprague-Dawley Rats were trained to a competent level in the 24 odor span test. The trained rats were dosed with either saline or CPP for subsequent trials. CPP was dissolved in 0.9% saline and delivered as 1 mL intraperitoneal injections having corresponding doses of 3, 10, and 17 mg/kg. In follow up sessions rat were dosed with 10 and 17 mg/kg of CPP along with 0.75 mg/kg of nicotine. Working memory was impaired by CPP in a dose dependent manner, although long term reference memory was recoverable. Nicotine did not ameliorate CPP-induced impairments in memory span or accuracy, but it did reduce the impairment of longest run time relative to 10 mg/kg CPP.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2905186
Microelectrophoretic studies were conducted on extracted rat neurons. Cells were incubated with 25mM CPP in 175 mm NaCl or 5mM CPP in 200mM NaCl. The firing rate of each neuron was recorded in response to cyclical ejection of the agonist. CPP was able to rapidly reduced excitations due to NMDA by ~ 80%. As a follow-up experiment in the same study, cortical wedges were taken from rat cingulate cortex and placed in a two compartment chamber with artificial cerebrospinal fluid. Depolarization of neurons in response to bath application of amino acids was recorded as a d.c. potential change across a grease seal barrier placed near the junction between grey and white matter. A dose response relationship was recorded by applying various concentrations of CPP. CPP was found to have an IC50 of 0.64 microM versus 40 microM cortical wedges.
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SUBSTANCE RECORD