D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid

Product NameD-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid
CAS117414-74-1
MFC8H15N2O5P
MW250.19
EINECS
MOL File117414-74-1.mol

Chemical Properties

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
pka	1.27±0.10(Predicted)
form	Powder
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

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

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

Preparation Products And Raw materials

D-4-[(2E)-3-Phosphono-2-propenyl]-2-piperazinecarboxylic acid Supplier

Related Product Information

Send Inquriy