phenidone

{{chembox

| Watchedfields = changed

| verifiedrevid = 464200287

| Name = Phenidone

| ImageFile = phenidone.svg

| ImageSize =

| ImageName =

| ImageFile1 = phenidone-spaceFill.png

| ImageSize1 =

| ImageName1 =

| PIN = 1-Phenylpyrazolidin-3-one

| OtherNames =

|Section1={{Chembox Identifiers

| SMILES = O=C2NN(c1ccccc1)CC2

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

| ChemSpiderID = 6823

| 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)

| InChIKey = CMCWWLVWPDLCRM-UHFFFAOYAF

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

| ChEMBL = 7660

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

| StdInChI = 1S/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12)

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

| StdInChIKey = CMCWWLVWPDLCRM-UHFFFAOYSA-N

| CASNo = 92-43-3

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

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

| UNII = H0U5612P6K

| EINECS = 202-155-1

}}

|Section2={{Chembox Properties

| C=9 | H=10 | N=2 | O=1

| Appearance = Crystal leaflets or needles

| Density =

| Solubility = 10 g/100 ml at 100 °C

| Solubility1 = 10 g/100 ml (hot)

| Solvent1 = ethanol

| Solubility2 = practically insoluble

| Solvent2 = diethyl ether

| MeltingPtC = 121

| pKa =

| Viscosity =

| Dipole =

}}

|Section7={{Chembox Hazards

| ExternalSDS = [https://fscimage.fishersci.com/msds/94187.htm External MSDS]

| MainHazards = Harmful if swallowed

| GHSPictograms = {{GHS07}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|411}}

| PPhrases = {{P-phrases|264|270|273|301+312|330|391|501}}

}}

}}

Phenidone (1-phenyl-3-pyrazolidinone) is an organic compound that is primarily used as a photographic developer. It has five to ten times the developing power as Metol, capable of achieving the same level of development in both less time and at a lower concentration.{{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}} It also has low toxicity and unlike some other developers, does not cause dermatitis upon skin contact.Merck Index of Chemicals and Drugs, 9th ed. monograph 7115 As a developer, Phenidone is typically used in conjunction with hydroquinone for black and white photography and performs better at lower pH levels.{{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}}

Phenidone is Ilford's trademark for this material, which was first filed on Feb. 24, 1953, but has since expired.{{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}} 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 reducing properties of this compound. Large scale production did not become feasible until 1951.Karlheinz Keller et al. "Photography" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. {{doi| 10.1002/14356007.a20_001}}

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:{{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}}

File:PhenidoneAction.png

Phenidone is also a dual cyclooxygenase/lipoxygenase inhibitor, capable of blocking the synthesis of arachidonic acid, which plays a role in causing inflammation in systemic inflammatory response syndrome{{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 and Therapy |language=en |pages=151 |doi=10.2147/BTT.S2542 |issn=1177-5475 |pmc=2727783 |pmid=19707438 |doi-access=free}} and neuronal damage in kainic acid-induced seizures.{{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}}

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