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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
Structure of 3-(2-CARBOXYPIPERAZIN-4-YL)PROPYL-1-PHOSPHONIC ACID

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)

HIDE SMILES / InChI

Molecular Formula C8H17N2O5P
Molecular Weight 252.2047
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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.

Originator

Curator's Comment: Davies J, Evans RH, Herrling PL, Jones AW, Olverman HJ, Pook P, Watkins JC.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
446.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Influence of pharmacological manipulations of NMDA and cholinergic receptors on working versus reference memory in a dual component odor span task.
2016 Jun
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:52:45 GMT 2023
Edited
by admin
on Sat Dec 16 09:52:45 GMT 2023
Record UNII
98Y1I8ZD4M
Record Status Validated (UNII)
Record Version
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Name Type Language
3-(2-CARBOXYPIPERAZIN-4-YL)PROPYL-1-PHOSPHONIC ACID
Common Name English
4-(3-PHOSPHONOPROPYL)-2-PIPERAZINECARBOXYLIC ACID
Systematic Name English
3-(2-CARBOXYPIPERAZIN-4-YL)PROPYL-1-PHOSPHONATE
Systematic Name English
CPP, (±)-
Common Name English
(±)-CPP
Common Name English
2-PIPERAZINECARBOXYLIC ACID, 4-(3-PHOSPHONOPROPYL)-
Systematic Name English
Code System Code Type Description
FDA UNII
98Y1I8ZD4M
Created by admin on Sat Dec 16 09:52:45 GMT 2023 , Edited by admin on Sat Dec 16 09:52:45 GMT 2023
PRIMARY
CAS
100828-16-8
Created by admin on Sat Dec 16 09:52:45 GMT 2023 , Edited by admin on Sat Dec 16 09:52:45 GMT 2023
PRIMARY
PUBCHEM
1228
Created by admin on Sat Dec 16 09:52:45 GMT 2023 , Edited by admin on Sat Dec 16 09:52:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID10905774
Created by admin on Sat Dec 16 09:52:45 GMT 2023 , Edited by admin on Sat Dec 16 09:52:45 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE