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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 412523026 | 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
Line 24: Line 25:
| 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
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}} }}


'''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>

{{clear-left}}


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


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


] ]
] ]
] ]
]

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Latest revision as of 02:36, 3 December 2024

Phenidone
Names
Preferred IUPAC name 1-Phenylpyrazolidin-3-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.960 Edit this at Wikidata
EC Number
  • 202-155-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12)Key: CMCWWLVWPDLCRM-UHFFFAOYSA-N
  • InChI=1/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12)Key: CMCWWLVWPDLCRM-UHFFFAOYAF
SMILES
  • O=C2NN(c1ccccc1)CC2
Properties
Chemical formula C9H10N2O
Molar mass 162.192 g·mol
Appearance Crystal leaflets or needles
Melting point 121 °C (250 °F; 394 K)
Solubility in water 10 g/100 ml at 100 °C
Solubility in ethanol 10 g/100 ml (hot)
Solubility in diethyl ether practically insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Harmful if swallowed
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H411
Precautionary statements P264, P270, P273, P301+P312, P330, P391, P501
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. It also has low toxicity and unlike some other developers, does not cause dermatitis upon skin contact. As a developer, Phenidone is typically used in conjunction with hydroquinone for black and white photography and performs better at lower pH levels.

Phenidone is Ilford's trademark for this material, which was first filed on Feb. 24, 1953, but has since expired. 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.

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:

Reaction of phenidone with silver bromide, as occurs in photographic development

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 and neuronal damage in kainic acid-induced seizures.

Preparation

Phenidone can be prepared by heating phenyl hydrazine with 3-chloropropanoic acid.

References

  1. Axford, A.J.; Kendall, J.D. (January 1, 1954). "Phenidone—Part 1; The Mechanism of its Developing Action and its Super-additivity with Hydroquinone *". The Journal of Photographic Science. 2 (1): 1–7. doi:10.1080/03700240.1954.11736538. ISSN 0370-0240.
  2. ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 7115
  3. Mason, L. F. A. (January 1, 1965). "Role of Phenidone in Modern Processing". The Journal of Photographic Science. 13 (4): 205–209. doi:10.1080/00223638.1965.11737306. ISSN 0022-3638.
  4. "Trademark Status & Document Retrieval". tsdr.uspto.gov. Retrieved 2024-11-19.
  5. Karlheinz Keller et al. "Photography" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_001
  6. Spirin, M. G.; Brichkin, S. B.; Razumov, V. F. (2002). "Phenidone Oxidation during Photoinitiated Chemical Reduction of AgBr Nanocrystals in Water Pools of Reverse Micelles". Colloid Journal. 64 (3): 364–368. doi:10.1023/A:1015981028758.
  7. Schroeder, Torsten (March 2008). "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". Biologics: Targets & Therapy: 151. doi:10.2147/BTT.S2542. ISSN 1177-5475. PMC 2727783. PMID 19707438.
  8. Kim, Hyoung-Chun; Jhoo, Wang-Kee; Bing, Guoying; Shin, Eun-Joo; Wie, Myung-Bok; Kim, Won-Ki; Ko, Kwang Ho (August 18, 2000). "Phenidone prevents kainate-induced neurotoxicity via antioxidant mechanisms". Brain Research. 874 (1): 15–23. doi:10.1016/S0006-8993(00)02560-9.
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