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| Names | |
|---|---|
| Preferred IUPAC name
1-Phenylpyrazolidin-3-one | |
| Other names
phenyl pyrazolidone
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.960 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H10N2O | |
| Molar mass | 162.192 g·mol−1 |
| Appearance | Crystal 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
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Harmful if swallowed |
| GHS labelling: | |
 
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| 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).
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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]
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
editPhenidone can be prepared by heating phenyl hydrazine with 3-chloropropanoic acid.[2]
References
edit- ^ a b 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.
- ^ a b Merck Index of Chemicals and Drugs, 9th ed. monograph 7115
- ^ "Trademark Status & Document Retrieval". tsdr.uspto.gov. Retrieved 2024-11-19.
- ^ Karlheinz Keller et al. "Photography" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_001
- ^ 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.
- ^ 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.
- ^ 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.
