Phenidone

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Phenidone
Phenidone.svg
Phenidone-spaceFill.png
Names
Preferred IUPAC name
1-Phenylpyrazolidin-3-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.960 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-155-1
PubChem CID
UNII
  • InChI=1S/C9H10N2O/c12-9-6-7-11(10-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,12) Yes check.svgY
    Key: CMCWWLVWPDLCRM-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C2NN(c1ccccc1)CC2
Properties
C9H10N2O
Molar mass 162.192 g·mol−1
AppearanceCrystal leaflets or needles
Melting point 121 °C (250 °F; 394 K)
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:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H411
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 [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] It also has low toxicity and unlike some other developers, does not cause dermatitis upon skin contact. [2] As a developer, Phenidone is typically used in conjunction with hydroquinone for black and white photography and performs better at lower pH levels. [3]

Phenidone is Ilford's trademark for this material, which was first filed on Feb. 24, 1953, but has since expired. [4] 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. [5]

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 [6] :

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

Phenidone is also a dual cyclooxygenase/lipoxygenase inhibitor, capable of blocking the synthesis ofarachidonic acid, which plays a role in causing inflammation in systemic inflammatory response syndrome [7] and neuronal damage in kainic acid-induced seizures. [8]

Preparation

Phenidone can be prepared by heating phenyl hydrazine with 3-chloropropanoic acid. [2]

Related Research Articles

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The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.

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<span class="mw-page-title-main">Hydroquinone</span> Chemical compound

Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.

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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. 1 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.