| Identification | Back Directory | [Name]
D-4-[(2E)-3-PHOSPHONO-2-PROPENYL]-2-PIPERAZINECARBOXYLIC ACID | [CAS]
117414-74-1 | [Synonyms]
D-CPP-ENE
Midafotel
DCPPene,D CPP ene
(R,E)-4-(3-PHOSPHONOPROP-2-ENYL)PIPERAZINE-2-CARBOXYLIC ACID
D-4-[(2E)-3-PHOSPHONO-2-PROPENYL]-2-PIPERAZINECARBOXYLIC ACID
(2R)-4-[(E)-3-Phosphono-2-propenyl]piperazine-2β-carboxylic acid
2-Piperazinecarboxylic acid, 4-[(2E)-3-phosphono-2-propenyl]-, (2R)- | [Molecular Formula]
C8H15N2O5P | [MDL Number]
MFCD00878116 | [MOL File]
117414-74-1.mol | [Molecular Weight]
250.19 |
| Chemical Properties | Back Directory | [Boiling point ]
555.6±60.0 °C(Predicted) | [density ]
1.449±0.06 g/cm3(Predicted) | [storage temp. ]
Desiccate at RT | [form ]
Powder | [pka]
1.27±0.10(Predicted) | [color ]
White | [Water Solubility ]
Soluble to 100 mM in water |
| Hazard Information | Back Directory | [Uses]
D-CPP-ene is a potent, competitive NMDA antagonist (1). NMDA antagonists such as this may increase sucrose intake through hunger satiation delay (2). | [Definition]
ChEBI: Midafotel is a member of the class of piperazines that is piperazine substituted by a carboxy group at position 2R and a (1E)-1-phosphonoprop-1-en-3-yl group at position 4. It is an antagonist of N-methyl-D-aspartate receptors (NMDARs) and was in clinical development by Novartis for the treatment of cognition disorders and brain injuries (now discontinued). It has a role as a NMDA receptor antagonist, a neuroprotective agent and an anticonvulsant. It is a piperazinecarboxylic acid, a monocarboxylic acid, a member of phosphonic acids, an olefinic compound and a tertiary amino compound. | [Biological Activity]
Potent and competitive NMDA antagonist (K i = 40 nM). Centrally active following systemic administration. | [in vivo]
Midafotel (15 mg/kg; i.p.) causes intense stereotyped behaviors in rats[2].
Midafotel (1.5, 4.5, 15 mg/kg; i.v.; initiated 15 min prior to MCA occlusion (followed by constant infusion at 1, 3 or 10 mg/kg/h)) produces dose-dependent reductions in the volumes of infarction; the dose of 4.5 mg/kg being the most effective in focal cerebral ischemia in the rat[3]. | Animal Model: | Adult female Wistar rats[2] | | Dosage: | 15 mg/kg | | Administration: | I.p. | | Result: | Induced the typical PCP-like behavioral syndrome with ataxia, hyperlocomotion and stereotyped behaviors, i.e., head weaving, stereotyped sniffing, face washing and grooming, significantly increased extracellular levels of HVA and 5-HIAA in the striatum. |
| [IC 50]
NMDA Receptor: 39 nM () | [storage]
Desiccate at RT |
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