Ifenprodil

Ifenprodil
Names
	IUPAC name 4-[2-(4-Benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
Identifiers
CAS Number	23210-56-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL305187 ;
ChemSpider	3561 ;
ECHA InfoCard	100.041.341
IUPHAR/BPS	5472;
KEGG	D08064 ;
PubChem CID	3689;
UNII	R8OE3P6O5S ;
CompTox Dashboard (EPA)	DTXSID2045656 ;
	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 Key: UYNVMODNBIQBMV-UHFFFAOYSA-N ; 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;
	SMILES OC(c1ccc(O)cc1)C(N2CCC(CC2)Cc3ccccc3)C;
Properties
Chemical formula	C21H27NO2
Molar mass	325.445
Pharmacology
ATC code	C04AX28 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ifenprodil is an inhibitor of the NMDA receptor,^[1] specifically of GluN1 (glycine-binding NMDA receptor subunit 1) and GluN2B (glutamate-binding NMDA receptor subunit 2) subunits.^[2] Additionally, ifenprodil inhibits GIRK channels, and interacts with alpha1 adrenergic, serotonin, and sigma receptors.^[3]

NMDA receptors are multimeric ionotropic glutamate receptors composed of four subunits. GluN1 is obligate for functional expression. Other subunits include GluN2A, GluN2B, and the more recently discovered GluN3 subunits. Ifenprodil selectively blocks NMDA receptors containing the GluN2B subunit.

References

^ 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.
^ 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. S2CID 195681796.
^ Kobayashi, Toru; Washiyama, Kazuo; Ikeda, Kazutaka (3 August 2005). "Inhibition of G Protein-Activated Inwardly Rectifying K+ Channels by Ifenprodil". Neuropsychopharmacology. 31 (3): 516–524. doi:10.1038/sj.npp.1300844. PMID 16123769.

[pmid2555674-1] 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. S2CID 195681796.

[3] Kobayashi, Toru; Washiyama, Kazuo; Ikeda, Kazutaka (3 August 2005). "Inhibition of G Protein-Activated Inwardly Rectifying K+ Channels by Ifenprodil". Neuropsychopharmacology. 31 (3): 516–524. doi:10.1038/sj.npp.1300844. PMID 16123769.

[1]

[2]

[3]

Names

IUPAC name 4-[2-(4-Benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
Identifiers
CAS Number	23210-56-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL305187
ChemSpider	3561
ECHA InfoCard	100.041.341
IUPHAR/BPS	5472
KEGG	D08064
PubChem CID	3689
UNII	R8OE3P6O5S
CompTox Dashboard (EPA)	DTXSID2045656
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 Key: UYNVMODNBIQBMV-UHFFFAOYSA-N 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
SMILES OC(c1ccc(O)cc1)C(N2CCC(CC2)Cc3ccccc3)C
Properties
Chemical formula	C₂₁H₂₇NO₂
Molar mass	325.445
Pharmacology
ATC code	C04AX28 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).