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Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone: Difference between revisions

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{{DISPLAYTITLE:Carbonyl cyanide-''p''-trifluoromethoxyphenylhydrazone}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 399705974
| Watchedfields = changed
⚫ | verifiedrevid = 414048120
| Name = Carbonyl cyanide-''p''-trifluoromethoxyphenylhydrazone
| ImageFile = Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone.svg | ImageFile = Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone.svg
| ImageSize = 250px | ImageSize = 250px
| PIN = ''N''-carbonohydrazonoyl dicyanide
| IUPACName =
| OtherNames = | OtherNames =
| Reference = <ref>, ].</ref> | Reference = <ref>, ].</ref>
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3213 | 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 | 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 | InChIKey = BMZRVOVNUMQTIN-UHFFFAOYAT
| SMILES1 = FC(F)(F)Oc1ccc(cc1)N/N=C(\C#N)C#N | SMILES1 = FC(F)(F)Oc1ccc(cc1)N/N=C(\C#N)C#N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 457504 | ChEMBL = 457504
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 17: Line 22:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BMZRVOVNUMQTIN-UHFFFAOYSA-N | StdInChIKey = BMZRVOVNUMQTIN-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 370-86-5 | CASNo = 370-86-5
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 3330
| UNII = SQR3W2FLV5
⚫ | SMILES = C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ | MeSHName = FCCP
| ChEBI = 75458
⚫ | PubChem = 3330
⚫ | SMILES = C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F
⚫ | MeSHName = FCCP
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = {{chem2|C10H5F3N4O}}
| Formula = C<sub>10</sub>H<sub>5</sub>F<sub>3</sub>N<sub>4</sub>O
| MolarMass = 254.16811 g/mol | MolarMass = 254.16811 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}

'''Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone''' ('''FCCP''') is an ] that is a mobile ]. It referred to as an ] because it disrupts ] ] by transporting ] through a ] before they can be used to provide the energy for ].<ref>, ].</ref> It is a ] and ]. '''Carbonyl cyanide-''p''-trifluoromethoxyphenylhydrazone''' ('''FCCP''') is an ] that is a mobile ]. It is referred to as an ] because it disrupts ] ] by transporting ] through the ] before they can be used to provide the energy for ].<ref>, ].</ref> It is a ] and ]. FCCP was first described in 1962 by Heytler.<ref>{{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 }}</ref>

⚫ == See also ==
⚫ * ] (CCCP)


==References== ==References==
{{reflist}} {{reflist}}


⚫ == See also ==
⚫ * ] (CCCP)
] ]
] ]
]

]

]
{{biochem-stub}}

]
]

Latest revision as of 05:50, 4 October 2023

Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone
Names
Preferred IUPAC name N-carbonohydrazonoyl dicyanide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.119 Edit this at Wikidata
MeSH FCCP
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16HKey: BMZRVOVNUMQTIN-UHFFFAOYSA-N
  • InChI=1/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16HKey: BMZRVOVNUMQTIN-UHFFFAOYAT
SMILES
  • C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F
  • FC(F)(F)Oc1ccc(cc1)N/N=C(\C#N)C#N
Properties
Chemical formula C10H5F3N4O
Molar mass 254.16811 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. It is a nitrile and hydrazone. FCCP was first described in 1962 by Heytler.

See also

References

  1. FCCP - Compound Summary, PubChem.
  2. MeSH Descriptor Data, MeSH.
  3. Heytler, P G (1962). "A new class of uncoupling agents — Carbonyl cyanide phenylhydrazones". Biochemical and Biophysical Research Communications. 7 (4): 272–275. doi:10.1016/0006-291X(62)90189-4. PMID 13907155.
Categories:
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