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Revision as of 12:45, 7 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit Latest revision as of 02:36, 3 December 2024 edit undoWikiCleanerBot (talk | contribs)Bots926,203 editsm v2.05b - Bot T21 CW#557 - Fix errors for CW project (Missing whitespace before a link - Reference before punctuation)Tag: WPCleaner 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 402524843 | verifiedrevid = 464200287
| Name = Phenidone
| ImageFile = phenidone.svg | Name = Phenidone
| ImageFile = phenidone.svg
| ImageSize = | ImageSize =
| ImageName = | ImageName =
| ImageFile1 = phenidone-spaceFill.png | ImageFile1 = phenidone-spaceFill.png
| ImageSize1 = | ImageSize1 =
| ImageName1 = | ImageName1 =
| PIN = 1-Phenylpyrazolidin-3-one
| IUPACName = 1-phenyl-3-pyrazolidinone
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| SMILES = O=C2NN(c1ccccc1)CC2 | SMILES = O=C2NN(c1ccccc1)CC2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6823 | ChemSpiderID = 6823
| PubChem = 7090 | PubChem = 7090
| InChI = 1/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12) | InChI = 1/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12)
| InChIKey = CMCWWLVWPDLCRM-UHFFFAOYAF | InChIKey = CMCWWLVWPDLCRM-UHFFFAOYAF
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 7660 | ChEMBL = 7660
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey = CMCWWLVWPDLCRM-UHFFFAOYSA-N | StdInChIKey = CMCWWLVWPDLCRM-UHFFFAOYSA-N
| CASNo = 92-43-3 | CASNo = 92-43-3
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | EINECS = 202-155-1
| UNII = H0U5612P6K
⚫ | EINECS = 202-155-1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=9 | H=10 | N=2 | O=1
| Formula = C<sub>9</sub>H<sub>10</sub>N<sub>2</sub>O
⚫ | Appearance = Crystal leaflets or needles
| MolarMass = 162.19
⚫ | Density =
⚫ | Appearance = Crystal leaflets or needles
⚫ | Solubility = 10 g/100 ml at 100 °C
⚫ | Density =
| Solubility = 10 g/100 ml at 100 °C | Solubility1 = 10 g/100 ml (hot)
⚫ | Solvent1 = ethanol
⚫ | Solubility1 = 10 g/100 ml (hot)
⚫ | Solubility2 = practically insoluble
⚫ | Solvent1 = ethanol
⚫ | Solvent2 = diethyl ether
⚫ | Solubility2 = practically insoluble
⚫ | MeltingPtC = 121
⚫ | Solvent2 = diethyl ether
| pKa =
⚫ | MeltingPtC = 121
| pKa = | Viscosity =
| Viscosity = | Dipole =
| Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = Harmful if swallowed | MainHazards = Harmful if swallowed
| RPhrases = {{R20}} {{R22}} | GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|411}}
| PPhrases = {{P-phrases|264|270|273|301+312|330|391|501}}
}} }}
<!-- | Section8 = {{Chembox Related <!--
|Section8={{Chembox Related
| OtherFunction_label =
| Function =
| OtherFunctn = }} --> | OtherFunction = }} -->
}} }}


'''Phenidone''' (1-phenyl-3-pyrazolidinone) is an organic chemical compound whose primary use is as a ]. It has five to ten times the developing power as ]. It also has low toxicity and, unlike some other developers, does not cause ] upon skin contact.<ref name="merck">''Merck Index of Chemicals and Drugs, 9th ed.'' monograph 7115</ref> '''Phenidone''' ('''1-phenyl-3-pyrazolidinone''') is an ] that is primarily used as a ]. It has five to ten times the developing power as ], capable of achieving the same level of development in both less time and at a lower concentration.<ref>{{Cite journal |last=Axford |first=A.J. |last2=Kendall |first2=J.D. |date=January 1, 1954 |title=Phenidone—Part 1; The Mechanism of its Developing Action and its Super-additivity with Hydroquinone * |url=http://www.tandfonline.com/doi/full/10.1080/03700240.1954.11736538 |journal=The Journal of Photographic Science |language=en |volume=2 |issue=1 |pages=1–7 |doi=10.1080/03700240.1954.11736538 |issn=0370-0240}}</ref> It also has low toxicity and unlike some other developers, does not cause ] upon skin contact.<ref name="merck">''Merck Index of Chemicals and Drugs, 9th ed.'' monograph 7115</ref> As a developer, Phenidone is typically used in conjunction with hydroquinone for black and white photography and performs better at lower pH levels.<ref>{{Cite journal |last=Mason |first=L. F. A. |date=January 1, 1965 |title=Role of Phenidone in Modern Processing |url=http://www.tandfonline.com/doi/full/10.1080/00223638.1965.11737306 |journal=The Journal of Photographic Science |language=en |volume=13 |issue=4 |pages=205–209 |doi=10.1080/00223638.1965.11737306 |issn=0022-3638}}</ref>


Phenidone is Ilford's trademark for this material which was first prepared in 1890. It was not until 1940 that Dr. J. D. Kendall, in the laboratories of Ilford Limited, discovered the photographic reducing properties of this chemical. However, large scale manufacturing of the compound did not become feasible until 1951 Phenidone is Ilford's trademark for this material, which was first filed on Feb. 24, 1953, but has since expired.<ref>{{Cite web |title=Trademark Status & Document Retrieval |url=https://tsdr.uspto.gov/#caseNumber=71642654&caseSearchType=US_APPLICATION&caseType=DEFAULT&searchType=statusSearch |access-date=2024-11-19 |website=tsdr.uspto.gov}}</ref> Although the compound was first prepared in 1890; it was not until 1940 that J. D. Kendall, in the laboratories of Ilford Limited, discovered the ] properties of this compound. Large scale production did not become feasible until 1951.<ref name=Ullmann>Karlheinz Keller et al. "Photography" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2005, Wiley-VCH, Weinheim. {{doi| 10.1002/14356007.a20_001}}</ref>

Phenidone functions as a reducing agent. It converts to the ''N''-phenyl-hydroxypyrazole. It is oxidized in acidic conditions, contributing the electrons it loses to reduce silver halides such as those found in film:<ref>{{Cite journal |last=Spirin |first=M. G. |last2=Brichkin |first2=S. B. |last3=Razumov |first3=V. F. |date=2002 |title=Phenidone Oxidation during Photoinitiated Chemical Reduction of AgBr Nanocrystals in Water Pools of Reverse Micelles |url=http://link.springer.com/10.1023/A:1015981028758 |journal=Colloid Journal |volume=64 |issue=3 |pages=364–368 |doi=10.1023/A:1015981028758}}</ref>
]

Phenidone is also a dual cyclooxygenase/lipoxygenase inhibitor, capable of blocking the synthesis of ], which plays a role in causing inflammation in ]<ref>{{Cite journal |last=Schroeder |first=Torsten |date=March 2008 |title=Activity of the lipoxygenase inhibitor 1-phenyl-3-pyrazolidinone (phenidone) and derivatives on the inhibition of adhesion molecule expression on human umbilical vascular endothelial cells |url=http://www.dovepress.com/activity-of-the-lipoxygenase-inhibitor-1-phenyl-3-pyrazolidinone-pheni-peer-reviewed-article-BTT |journal=Biologics: Targets & Therapy |language=en |pages=151 |doi=10.2147/BTT.S2542 |issn=1177-5475 |pmc=2727783 |pmid=19707438 |doi-access=free}}</ref> and neuronal damage in kainic acid-induced seizures.<ref>{{Cite journal |last=Kim |first=Hyoung-Chun |last2=Jhoo |first2=Wang-Kee |last3=Bing |first3=Guoying |last4=Shin |first4=Eun-Joo |last5=Wie |first5=Myung-Bok |last6=Kim |first6=Won-Ki |last7=Ko |first7=Kwang Ho |date=August 18, 2000 |title=Phenidone prevents kainate-induced neurotoxicity via antioxidant mechanisms |url=https://linkinghub.elsevier.com/retrieve/pii/S0006899300025609 |journal=Brain Research |language=en |volume=874 |issue=1 |pages=15–23 |doi=10.1016/S0006-8993(00)02560-9}}</ref>

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==Preparation== ==Preparation==
Phenidone is prepared by heating ] with ] also called ].<ref name="merck"/> Phenidone can be prepared by heating ] with ].<ref name="merck"/>


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


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