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
Density 1.188 +/- 0.06 g/mol
Melting point 121 °C (250 °F; 394 K)
Boiling point 288.88 °C (551.98 °F; 562.03 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 ten to eighteen times the amount of efficiency and stability 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 (about 9.8-10.4). [1] This is comparable to Metol whose working pH is approximately 10.3.

Phenidone is Ilford's trademark for this material, which was first filed on Feb. 24, 1953, but has since expired. [3] 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. [4] It begun to be used by large companies, such as Agfa/Orwo, in the 1960s in place of Metol.

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: [5]

Reaction of phenidone with silver bromide, as occurs in photographic development PhenidoneAction.svg
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 [6] and neuronal damage in kainic acid-induced seizures. [7]

Preparation

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

References

  1. 1 2 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. ↑ "Trademark Status & Document Retrieval". tsdr.uspto.gov. Retrieved 2024-11-19.
  4. ↑ Karlheinz Keller et al. "Photography" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a20_001
  5. ↑ 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.
  6. ↑ 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 and Therapy: 151. doi: 10.2147/BTT.S2542 . ISSN   1177-5475. PMC   2727783 . PMID   19707438.
  7. ↑ 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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