Ifenprodil

Ifenprodil
IUPAC name 4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
Identifiers
	PubChem	3689
ChemSpider	3561 Y
KEGG	D08064 Y
ChEMBL	CHEMBL113830 N
ATC code	C04AX28
Jmol-3D images	Image 1
SMILES OC(c1ccc(O)cc1)C(N2CCC(CC2)Cc3ccccc3)C
InChI InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3 Y Key: UYNVMODNBIQBMV-UHFFFAOYSA-N Y InChI=1/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3 Key: UYNVMODNBIQBMV-UHFFFAOYAU
Properties
Molecular formula	C21H27NO2
Molar mass	325.445
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ifenprodil is a selective inhibitor of the NMDA receptor.^[1] Its effect is specific to receptors composed of the NR1 (glycine-binding NMDA receptor subunit 1; GluN1) and NR2B (glutamate-binding NMDA receptor subunit 2; GluN2B) subunits.^[2]

NMDA receptors are multimeric ionotropic glutamate receptors composed of four subunits. NR1 is obligate for functional expression. Other subunits include NR2A, NR2B, and the more recently discovered NR3 subunits. Ifenprodil selectively blocks NMDA receptors containing the NR2B subunit.

References

1. ↑ Reynolds IJ, Miller RJ (1989). "Ifenprodil is a novel type of N-methyl-D-aspartate receptor antagonist: interaction with polyamines". Mol. Pharmacol. 36 (5): 758–65. PMID 2555674. 
2. ↑ Korinek M, Kapras V, Vyklicky V, Adamusova E, Borovska J, Vales K, Stuchlik A, Horak M, Chodounska H, Vyklicky L Jr (Dec 2011). "Neurosteroid modulation of N-methyl-d-aspartate receptors: Molecular mechanism and behavioral effects". Steroids 76 (13): 1409–18. doi:10.1016/j.steroids.2011.09.002. PMID 21925193.