A σ1 receptor agonist and a NR1A/2B subunit-containing NMDA receptor antagonist
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4-PPBP (maleate)

Item No. 46468

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-phenyl-1-(4-phenylbutyl)-piperidine, 2Z-butenedioate
CAS Number
201216-39-9
Molecular Formula
C21H27N • C4H4O4
Formula Weight
409.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/ml
SMILES
OC(/C=C\C(O)=O)=O.C1(CCCCN2CCC(C3=CC=CC=C3)CC2)=CC=CC=C1
InChi Code
InChI=1S/C21H27N.C4H4O4/c1-3-9-19(10-4-1)11-7-8-16-22-17-14-21(15-18-22)20-12-5-2-6-13-20;5-3(6)1-2-4(7)8/h1-6,9-10,12-13,21H,7-8,11,14-18H2;1-2H,(H,5,6)(H,7,8)/b;2-1-
InChi Key
OASPNIMFGJVLES-BTJKTKAUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $68

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    10 mg

    $129

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    25 mg

    $272

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    50 mg

    $442

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    Product Description

    4-PPBP is an agonist of the sigma-1 (σ1) receptor and an antagonist of NR1A/2B subunit-containing NMDA receptors.1,2 It selectively inhibits calcium currents in Xenopus oocytes expressing the NR1A/2B subunit-containing NMDA receptor (IC50 = 2.2 µM) over those expressing the NR1A/2A or NR1A/2C subunits (IC50s = >100 µM for both).2 4-PPBP reduces cell death induced by glutamate or oxygen-glucose deprivation in primary rat cortical neurons and reduces infarct volumes in rat and cat models of transient focal ischemia.1,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yang, S., Bhardwaj, A., Cheng, J., et al. Sigma receptor agonists provide neuroprotection in vitro by preserving bcl-2. Anesth. Analg. 104(5), 1179-1184 (2007).

    2. Guzikowski, A.P., Tamiz, A.P., Acosta-Burruel, M., et al. Synthesis of N-substituted 4-(4-hydroxyphenyl)piperidines, 4-(4-hydroxybenzyl)piperidines, and (±)-3-(4-hydroxyphenyl)pyrrolidines: Selective antagonists at the 1A/2B NMDA receptor subtype. J. Med. Chem. 43(5), 984-994 (2000).

    3. Takahashi, H., Kirsch, J.R., Hashimoto, K., et al. PPBP [4-phenyl-1-(4-phenylbutyl)piperidine] decreases brain injury after transient focal ischemia in rats. Stroke 27(11), 2120-2123 (1996).

    4. Takahashi, H., Kirsch, J.R., Hashimoto, K., et al. PPBP [4-phenyl-1-(4-phenylbutyl)piperidine], a potent sigma-receptor ligand, decreases brain injury after transient focal ischemia in cats. Stroke 26(9), 1676-1682 (1995).