Synonym
D-CPP-ene; SDZ-EAA 494; SDZ-EAA-494; SDZ-EAA494; Midafotel
IUPAC/Chemical Name
(R)-4-((E)-3-Phosphonoallyl)-2-piperazinecarboxylic acid
InChi Key
VZXMZMJSGLFKQI-ABVWVHJUSA-N
InChi Code
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
SMILES Code
O=C([C@@H]1NCCN(C/C=C/P(O)(O)=O)C1)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Midafotel is a potent, competitive antagonist at the NMDA receptor.
In vitro activity:
D-CPP-ene (SDZ EAA 494) was the most active competitive antagonist with a threshold concentration of 10 nM and an ED50 of 39 nM. D-CPP-ene was also the most potent competitive antagonist against NMDA-evoked depolarizations, having an apparent pA2 value of 6.8; its action was specific to the NMDA type of excitatory amino acid receptor.
Reference: Neurosci Lett. 1990 Jun 8;113(3):315-21. https://pubmed.ncbi.nlm.nih.gov/2166255/
In vivo activity:
When administered systemically, D-CPPene, 15 mg/kg i.p., caused more intense stereotyped behaviors in kindled than in non-kindled rats. While there was no significant alteration in extracellular dopamine, in both groups of rats HVA and 5-HIAA significantly increased. In kindled rats, basal levels of HVA and the increase in HVA in response to D-CPPene were higher compared to non-kindled animals. When administered intrastriatally via the microdialysis probe, D-CPPene, 10 microM, significantly increased dopamine, HVA and 5-HIAA, which was associated with stereotyped behaviors.
Reference: Eur J Pharmacol. 1999 Jun 18;374(2):175-87. https://pubmed.ncbi.nlm.nih.gov/10422758/
|
Solvent |
mg/mL |
mM |
comments |
Solubility |
Water |
25.0 |
99.92 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
250.19
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Lowe DA, Neijt HC, Aebischer B. D-CPP-ene (SDZ EAA 494), a potent and competitive N-methyl-D-aspartate (NMDA) antagonist: effect on spontaneous activity and NMDA-induced depolarizations in the rat neocortical slice preparation, compared with other CPP derivatives and MK-801. Neurosci Lett. 1990 Jun 8;113(3):315-21. doi: 10.1016/0304-3940(90)90604-8. PMID: 2166255.
2. Potschka H, Fedrowitz M, Löscher W. Effects of the NMDA receptor antagonist D-CPPene on extracellular levels of dopamine and dopamine and serotonin metabolites in striatum of kindled and non-kindled rats. Eur J Pharmacol. 1999 Jun 18;374(2):175-87. doi: 10.1016/s0014-2999(99)00311-8. PMID: 10422758.
3. Wlaź P, Ebert U, Potschka H, Löscher W. Electrical but not chemical kindling increases sensitivity to some phencyclidine-like behavioral effects induced by the competitive NMDA receptor antagonist D-CPPene in rats. Eur J Pharmacol. 1998 Jul 24;353(2-3):177-89. doi: 10.1016/s0014-2999(98)00409-9. PMID: 9726648.
In vitro protocol:
1. Lowe DA, Neijt HC, Aebischer B. D-CPP-ene (SDZ EAA 494), a potent and competitive N-methyl-D-aspartate (NMDA) antagonist: effect on spontaneous activity and NMDA-induced depolarizations in the rat neocortical slice preparation, compared with other CPP derivatives and MK-801. Neurosci Lett. 1990 Jun 8;113(3):315-21. doi: 10.1016/0304-3940(90)90604-8. PMID: 2166255.
In vivo protocol:
1. Potschka H, Fedrowitz M, Löscher W. Effects of the NMDA receptor antagonist D-CPPene on extracellular levels of dopamine and dopamine and serotonin metabolites in striatum of kindled and non-kindled rats. Eur J Pharmacol. 1999 Jun 18;374(2):175-87. doi: 10.1016/s0014-2999(99)00311-8. PMID: 10422758.
2. Wlaź P, Ebert U, Potschka H, Löscher W. Electrical but not chemical kindling increases sensitivity to some phencyclidine-like behavioral effects induced by the competitive NMDA receptor antagonist D-CPPene in rats. Eur J Pharmacol. 1998 Jul 24;353(2-3):177-89. doi: 10.1016/s0014-2999(98)00409-9. PMID: 9726648.
1: Bespalov A, Kudryashova M, Zvartau E. Prolongation of morphine analgesia by competitive NMDA receptor antagonist D-CPPene (SDZ EAA 494) in rats. Eur J Pharmacol. 1998 Jun 26;351(3):299-305. PubMed PMID: 9721021.
2: Rockstroh S, Emre M, Tarral A, Pokorny R. Effects of the novel NMDA-receptor antagonist SDZ EAA 494 on memory and attention in humans. Psychopharmacology (Berl). 1996 Apr;124(3):261-6. PubMed PMID: 8740048.
3: Lowe DA, Emre M, Frey P, Kelly PH, Malanowski J, McAllister KH, Neijt HC, Rüdeberg C, Urwyler S, White TG, et al. The pharmacology of SDZ EAA 494, a competitive NMDA antagonist. Neurochem Int. 1994 Dec;25(6):583-600. PubMed PMID: 7894335.
4: Wiley JL, Balster RL. Effects of competitive and non-competitive N-methyl-D-aspartate (NMDA) antagonists in squirrel monkeys trained to discriminate D-CPPene (SDZ EAA 494) from vehicle. Psychopharmacology (Berl). 1994 Nov;116(3):266-72. PubMed PMID: 7892415.
5: Sveinbjornsdottir S, Sander JW, Upton D, Thompson PJ, Patsalos PN, Hirt D, Emre M, Lowe D, Duncan JS. The excitatory amino acid antagonist D-CPP-ene (SDZ EAA-494) in patients with epilepsy. Epilepsy Res. 1993 Oct;16(2):165-74. PubMed PMID: 8269915.
6: Lowe DA, Neijt HC, Aebischer B. D-CPP-ene (SDZ EAA 494), a potent and competitive N-methyl-D-aspartate (NMDA) antagonist: effect on spontaneous activity and NMDA-induced depolarizations in the rat neocortical slice preparation, compared with other CPP derivatives and MK-801. Neurosci Lett. 1990 Jun 8;113(3):315-21. PubMed PMID: 2166255.