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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
3D model (JSmol)
ChEMBL
ChemSpider
MeSH 4-phenyl-1-(4-phenylbutyl)piperidine
UNII
  • 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,7-8,11,14-18H2 checkY
    Key: HQGDPZPNAXRCSA-UHFFFAOYSA-N checkY
  • 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,7-8,11,14-18H2
    Key: HQGDPZPNAXRCSA-UHFFFAOYAV
  • C1CN(CCC1C2=CC=CC=C2)CCCCC3=CC=CC=C3
  • c1ccccc1C3CCN(CCCCc2ccccc2)CC3
Properties
C21H27N
Molar mass 293.446 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

4-PPBP is a neuroprotective cyclic amine which binds to sigma receptors.[1]

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 Ca2+ dysregulation.[2] 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.[3]

See also

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References

[edit]
  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.


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