Phenidone

Phenidone
	source ↗
	source ↗
Names
	Preferred IUPAC name 1-Phenylpyrazolidin-3-one
	Other names phenyl pyrazolidone
Identifiers
CAS Number	92-43-3 Y;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL7660 Y;
ChemSpider	6823 Y;
ECHA InfoCard	100.001.960
EC Number	202-155-1;
PubChem CID	7090;
UNII	H0U5612P6K Y;
CompTox Dashboard (EPA)	DTXSID1049433 ;
	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) Y Key: CMCWWLVWPDLCRM-UHFFFAOYSA-N Y; 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−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)
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
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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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 source ↗

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 syndrome⁶ and neuronal damage in kainic acid-induced seizures.⁷

Preparation

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

References

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.
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.

[:0-1] 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.

[merck-2] Merck Index of Chemicals and Drugs, 9th ed. monograph 7115

[3] "Trademark Status & Document Retrieval". tsdr.uspto.gov. Retrieved 2024-11-19.

[Ullmann-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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