:4-PPBP

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477223250

| ImageFile=4-phenyl-1-(4-phenylbutyl) piperidine.svg

| ImageSize=250

| ImageAlt = Skeletal formula of 4-PPBP

| ImageFile1 = 4-PPBP-3D-balls.png

| ImageSize1 = 250

| ImageAlt1 = Ball-and-stick model of the 4-PPBP molecule

| PIN=4-Phenyl-1-(4-phenylbutyl)piperidine

| OtherNames=

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2299855

| 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

| InChIKey = HQGDPZPNAXRCSA-UHFFFAOYAV

| SMILES1 = c1ccccc1C3CCN(CCCCc2ccccc2)CC3

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 325238

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HQGDPZPNAXRCSA-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo=136534-70-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = HDL2DSB8CH

| PubChem=3035672

| SMILES = C1CN(CCC1C2=CC=CC=C2)CCCCC3=CC=CC=C3

| MeSHName=4-phenyl-1-(4-phenylbutyl)piperidine

}}

|Section2={{Chembox Properties

| Formula =

| C=21 | H=27 | N=1

| MolarMass=293.446 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

4-PPBP is a neuroprotective cyclic amine which binds to sigma receptors.{{cite journal | vauthors = Yang S, Bhardwaj A, Cheng J, Alkayed NJ, Hurn PD, Kirsch JR | title = Sigma receptor agonists provide neuroprotection in vitro by preserving bcl-2 | journal = Anesthesia and Analgesia | volume = 104 | issue = 5 | pages = 1179–84, tables of contents | date = May 2007 | pmid = 17456670 | pmc = 2596726 | doi = 10.1213/01.ane.0000260267.71185.73 }}

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.{{cite journal | vauthors = Yang ZJ, Carter EL, Torbey MT, Martin LJ, Koehler RC | title = 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 | journal = Experimental Neurology | volume = 221 | issue = 1 | pages = 166–74 | date = January 2010 | pmid = 19883643 | pmc = 2812675 | doi = 10.1016/j.expneurol.2009.10.019 }} 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.{{cite journal | vauthors = Yang S, Alkayed NJ, Hurn PD, Kirsch JR | title = Cyclic adenosine monophosphate response element-binding protein phosphorylation and neuroprotection by 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP) | journal = Anesthesia and Analgesia | volume = 108 | issue = 3 | pages = 964–70 | date = March 2009 | pmid = 19224810 | pmc = 2828492 | doi = 10.1213/ane.0b013e318192442c }}