HuagongsheHuagongshe Chemistry Print Report · For research reference only
Mci-186
1-PHENYL-3-METHYL-5-PYRAZOLONE · 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one · 5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one · 1,2-Dihydro-5-methyl · Edaravone Impurity 9 · Edaravone Impurity 16 · Edaravone Related Compound · Edaravone Related Compound 1
Identifiers & Physical Properties
| CAS No. | 19735-89-8 |
|---|---|
| Molecular formula | C10H10N2O |
| Average molar mass | 174.2 g/mol |
| Monoisotopic mass | 174.07931294 g/mol |
| SMILES | CC1=NN(c2ccccc2)C(=O)C1 |
| InChIKey | QELUYTUMUWHWMC-UHFFFAOYSA-N |
| PubChem CID | 4021 |
| ChEMBL | CHEMBL290916 |
| ChEBI | CHEBI:31530 |
| EC No. | 201-891-0 |
| DTXSID | DTXSID9021130 |
Chemical & Physical Properties
| XLogP | 1.3 |
|---|---|
| Topological polar surface area | 32.7 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 241 |
| Chemical classes | Nitrogen Compounds -> Pyrazoles |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Cosmetics | Cosmetic ingredients (Phenyl Methyl Pyrazolone) -> CIR (Cosmetic Ingredient Review)Hair dyeing |
| Color/Form | MONOCLINIC PRISMS FROM WATERWHITE POWDER OR CRYSTALS |
| Solubility | less than 1 mg/mL at 73 °F (NTP, 1992)SOL IN HOT WATER & HOT ALCOHOLSLIGHTLY SOL IN BENZENEINSOL IN PETROLEUM ETHER25.4 [ug/mL] (The mean of the results at pH 7.4) |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Boiling point | 549 °F at 105 mmHg (NTP, 1992)191 °C @ 17 MM HG287 °C @ 105 MM HG305.17°C (rough estimate) |
| Melting point | 261 to 266 °F (NTP, 1992)127 °C128.9 °C128°C |
| Vapor pressure | less than 0.01 mmHg at 68 °F (NTP, 1992)LESS THAN 0.01 MM @ 20 °C |
| Refractive index | MAX ABSORPTION (ALCOHOL): 280 NM SHOULDER (LOG E= 3.6) INDEX OF REFRACTION: 1.637MAX ABSORPTION (ALCOHOL): 245 NM (LOG E= 1.1)1.6370 (estimate) |
| Physical Description | 1-phenyl-3-methyl-5-pyrazolone appears as white to off-white powder or crystals. (NTP, 1992)White solid[Merck Index] Light yellow odorless powder[Alfa Aesar MSDS] |
| Dissociation Constants | 7.0 |
| Density | 1.2600 |
| Storage conditions | Store at room temperature |
| pKa (acidity coefficient) | 0.10±0.40(Predicted) |
| Appearance | Light yellow to yellow Solid |
| CAS DataBase Reference | 19735-89-8 |
| FDA UNII | S798V6YJRP |
| EPA Substance Registry System | 1-Phenyl-3-methyl-5-pyrazolone (19735-89-8) |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 7.7% (16 of 209) of reports.WarningH302 (26.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 209 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-Status: Active Update: 15-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/225413H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-: Human health tier II assessment |
| Fire hazards | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. |
| Hazards summary | Emergency treatment: Irritants[HSDB] A skin, eye, and mucous membrane irritant[CAMEO] Causes no to mild skin and eye irritation in rabbitsNot sensitizing to guinea pig skin[IUCLID] No teratogenicity observed in experimental animals, but reduced birth weight and fetal loss seen at high doses[REPROTOX] No evidence for carcinogenicity in mice or rats[NTP] A mild eye irritantCauses changes in liver and spleen in intravenous studies of dogs[RTECS] |
| Reactive group | Amides and Imides |
| Special Reports | DHEW/NCIBioassay of 1-Phenyl-3-methyl-5-pyrazolone for Possible Carcinogenicity (1978) Technical Rpt Series No. 141 DHEW Pub No. (NIH) 78-1396 |
| Reactivity Profile | Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (26.8%)Skin sensitisation - category 1 |
| Fire fighting | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Protective Action Criteria (PAC) | 5.7 [mg/m3]63 [mg/m3]380 [mg/m3] |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Hepatotoxicity | Serum aminotransferase elevations occur in a small proportion of patients on edaravone therapy, but the frequency, timing of onset, duration and severity of these elevations has not been defined. The rates of abnormal liver tests during edaravone therapy were said to be similar to those during placebo treatment. Most elevations resolved spontaneously, and there were no reports of drug discontinuation for serum enzyme elevations. Clinically apparent liver injury due to edaravone was not reported in the prelicensure trials and has not been reported with subsequent clinical use of edaravone, but the numbers of patients treated have been few. Thus, clinically apparent liver injury from edaravone must be rare if it occurs at all. |
| Toxicity summary | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=89-25-8] |
| Carcinogen Classification | 1-Phenyl-3-methyl-5-pyrazoloneTR-141: Bioassay of 1-Phenyl-3-methyl-5-pyrazolone for Possible Carcinogenicity (CASRN 89-25-8) (1978 )06/29/78No Evidence |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)EdaravonevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Non-Human Toxicity Excerpts | ... Levels of Evidence of Carcinogenicity: Male Rats: NegativeFemale Rats: NegativeMale Mice: NegativeFemale Mice: Negative. |
| National Toxicology Program Studies | A bioassay of 1-phenyl-3-methyl-5-pyrazolone for possible carcinogenicity was conducted using Fischer 344 rats and B6C3Fl mice. l-Phenyl-3-methyl-5-pyrazolone was admin in the feed, at either of two concn, to groups of 49 or 50 male and 50 female animals of each species. The high and low concn of 1-phenyl-3-methyl-5-pyrazolone utilized were, respectively, 5,000 and 2,500 ppm for rats and 15,000 and 7,500 ppm for mice. Twenty animals of each species and sex were placed on test as controls. After a 103 wk period of chemical admin, there was an additional observation period of 2 wk for rats. A 102 wk period of chemical admin was followed by an additional 2 wk observation period for mice. In both species adequate numbers of animals survived sufficiently long to be at risk from late developing tumors. ... Under the conditions of this bioassay, there was no evidence for the carcinogenicity of 1-phenyl-3-methyl-5-pyrazolone to Fischer 344 rats or B6C3Fl mice. ... Levels of Evidence of Carcinogenicity: Male Rats: NegativeFemale Rats: NegativeMale Mice: NegativeFemale Mice: Negative. |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
Applications & Uses
Uses
1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one is an important class of heterocyclic compounds with physiological functions. It can be used as an antipyretic, analgesic, and antibacterial agent, as well as an analytical reagent, an antioxidant for rubber and flaxseed, and a dye for textiles.