Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone

{{DISPLAYTITLE:Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 414048120

| Name = Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone

| ImageFile = Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone.svg

| ImageSize = 250px

| PIN = N-[4-(Trifluoromethoxy)phenyl]carbonohydrazonoyl dicyanide

| OtherNames =

| Reference = [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3330&loc=ec_rcs FCCP - Compound Summary], PubChem.

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 3213

| InChI = 1/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H

| InChIKey = BMZRVOVNUMQTIN-UHFFFAOYAT

| SMILES1 = FC(F)(F)Oc1ccc(cc1)N/N=C(\C#N)C#N

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

| ChEMBL = 457504

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

| StdInChI = 1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H

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

| StdInChIKey = BMZRVOVNUMQTIN-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 370-86-5

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

| UNII = SQR3W2FLV5

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 75458

| PubChem = 3330

| SMILES = C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F

| MeSHName = FCCP

}}

|Section2={{Chembox Properties

| Formula = {{chem2|C10H5F3N4O}}

| MolarMass = 254.16811 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

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Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone (FCCP) is an ionophore that is a mobile ion carrier. It is referred to as an uncoupling agent because it disrupts ATP synthesis by transporting hydrogen ions through the mitochondrial membrane before they can be used to provide the energy for oxidative phosphorylation.[https://www.nlm.nih.gov/cgi/mesh/2007/MB_cgi?mode=&term=FCCP MeSH Descriptor Data], MeSH. It is a nitrile and hydrazone. FCCP was first described in 1962 by Heytler.{{cite journal |author=Heytler, P G |title=A new class of uncoupling agents — Carbonyl cyanide phenylhydrazones |journal=Biochemical and Biophysical Research Communications |volume=7 |issue=4 |pages=272–275 |year=1962 | doi=10.1016/0006-291X(62)90189-4|pmid=13907155 }}