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4-PPBP

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4-PPBP
Skeletal formula of 4-PPBP
Ball-and-stick model of the 4-PPBP molecule
Names
Preferred IUPAC name 4-Phenyl-1-(4-phenylbutyl)piperidine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH 4-phenyl-1-(4-phenylbutyl)piperidine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H27N/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/h1-6,9-10,12-13,21H,7-8,11,14-18H2Key: HQGDPZPNAXRCSA-UHFFFAOYSA-N
  • InChI=1/C21H27N/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/h1-6,9-10,12-13,21H,7-8,11,14-18H2Key: HQGDPZPNAXRCSA-UHFFFAOYAV
SMILES
  • C1CN(CCC1C2=CC=CC=C2)CCCCC3=CC=CC=C3
  • c1ccccc1C3CCN(CCCCc2ccccc2)CC3
Properties
Chemical formula C21H27N
Molar mass 293.446 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

4-PPBP is a neuroprotective cyclic amine which binds to sigma receptors.

4-PPBP decreases neuronal nitric oxide synthase (nNOS) activity and ischemia-evoked nitric oxide (NO) production. 4-PPBP provides neuroprotection; this involves the prevention of ischemia-induced intracellular Ca dysregulation. 4-PPBP protects neurons using a mechanism that activates the transcription factor cyclic adenosine monophosphate response element-binding protein (CREB). Neuroprotection that is associated with 4-PPBP increases Bcl-2 expression; Bcl-2 expression is regulated by CREB.

See also

References

  1. Yang S, Bhardwaj A, Cheng J, Alkayed NJ, Hurn PD, Kirsch JR (May 2007). "Sigma receptor agonists provide neuroprotection in vitro by preserving bcl-2". Anesthesia and Analgesia. 104 (5): 1179–84, tables of contents. doi:10.1213/01.ane.0000260267.71185.73. PMC 2596726. PMID 17456670.
  2. Yang ZJ, Carter EL, Torbey MT, Martin LJ, Koehler RC (January 2010). "Sigma receptor ligand 4-phenyl-1-(4-phenylbutyl)-piperidine modulates neuronal nitric oxide synthase/postsynaptic density-95 coupling mechanisms and protects against neonatal ischemic degeneration of striatal neurons". Experimental Neurology. 221 (1): 166–74. doi:10.1016/j.expneurol.2009.10.019. PMC 2812675. PMID 19883643.
  3. Yang S, Alkayed NJ, Hurn PD, Kirsch JR (March 2009). "Cyclic adenosine monophosphate response element-binding protein phosphorylation and neuroprotection by 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP)". Anesthesia and Analgesia. 108 (3): 964–70. doi:10.1213/ane.0b013e318192442c. PMC 2828492. PMID 19224810.
Sigma receptor modulators
σ1
σ2
Unsorted
See also: Receptor/signaling modulators


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