D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid
![D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid Structure](CAS/GIF/117414-74-1.gif)
- CAS No.
- 117414-74-1
- Chemical Name:
- D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid
- Synonyms
- Midafotel;D-CPP-ENE;(R)-CPPene;DCPPene,D CPP ene;(R)-CPPene (SDZ EAA 494);(R)-CPPene (SDZ EAA 494) (mM/ml), NMDA antagonist;(R)-CPPene (SDZ EAA 494), competitive NMDA antagonist;(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
- CBNumber:
- CB2158312
- Molecular Formula:
- C8H15N2O5P
- Molecular Weight:
- 250.19
- MDL Number:
- MFCD00878116
- MOL File:
- 117414-74-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Boiling point | 555.6±60.0 °C(Predicted) |
|---|---|
| Density | 1.449±0.06 g/cm3(Predicted) |
| storage temp. | Desiccate at RT |
| solubility | H2O: 100 mM |
| form | Powder |
| pka | 1.27±0.10(Predicted) |
| color | White |
| Water Solubility | Soluble to 100 mM in water |
| InChI | 1S/C8H15N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h1,5,7,9H,2-4,6H2,(H,11,12)(H2,13,14,15)/b5-1+/t7-/m1/s1 |
| InChIKey | VZXMZMJSGLFKQI-ABVWVHJUSA-N |
| FDA UNII | 7LYU6ZF84G |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid price More Price(13)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 5.04840 | (R)-CPPene - CAS 117414-74-1 - Calbiochem | 117414-74-1 | 10mg | $344 | 2023-06-20 | Buy |
| Usbiological | 445521 | D-CPP-ene | 117414-74-1 | 10mg | $631 | 2026-06-03 | Buy |
| Usbiological | 445521 | D-CPP-ene | 117414-74-1 | 25mg | $1296 | 2026-06-03 | Buy |
| Usbiological | 255089 | D-CPP-ene Asreported | 117414-74-1 | 10mg | $715 | 2026-06-03 | Buy |
| Usbiological | 217730 | (R)-CPPene ((R)-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic Acid, SDZ EAA 494, Midafotel) ≥99%(HPLC) | 117414-74-1 | 10mg | $596 | 2026-06-03 | Buy |
D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid Chemical Properties, Uses, Production
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
Room temperature
D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid Preparation Products And Raw materials
D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Beijing HuaMeiHuLiBiological Chemical | 010-56205725 | waley188@sohu.com | China | 12323 | 58 |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8435 | 60 |
| BOC Sciences | 16314854226; +8616314854226 | inquiry@bocsci.com | United States | 19852 | 58 |
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| MedBioPharmaceutical Technology Inc | 021-69568360 18916172912 | order@med-bio.cn | China | 8137 | 58 |
| Nantong QuanYi Biotechnology Co., Ltd | 0513-66337626 18051384581 | sales@chemhifuture.com | China | 5985 | 58 |
| Aladdin Scientific | tp@aladdinsci.com | United States | 50068 | 58 |
