4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

• ChemBase ID: 1232
• Molecular Formular: C13H17N3O
• Molecular Mass: 231.29358
• Monoisotopic Mass: 231.13716218
• SMILES: O=c1n(n(c(c1N(C)C)C)C)c1ccccc1
• Canonical SMILES: CN(c1c(C)n(n(c1=O)c1ccccc1)C)C
• InChI: InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3
• InChIKey: RMMXTBMQSGEXHJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
• IUPAC Traditional name: aminophenazone
• Synonyms: 4-Dimethylamino-2,3-dimethyl-1-phenylpyrazol-5-one; 4-(Dimethylamino)antipyrine; 4-Dimethylaminoantipyrine; Aminopyrine; Dipyrine; Aminophenazone; 4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; 4-DIMETHYLAMINOANTIPYRINE; AMINOPYRINE; 4-Dimethylaminoantipyrine; Amidopyrine; 4-二甲氨基-2,3-二甲氧-1-苯基吡唑-5-酮

Database IDs

• CAS Number: 58-15-1
• EC Number: 200-365-8
• MDL Number: MFCD00003142
• Merck Index: 14474
• PubChem SID: 24894178; 160964692; 46504975
• PubChem CID: 6009

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.1466073
• LogD (pH = 7.4): 1.1505445
• Log P: 1.150595
• Molar Refractivity: 70.111 cm^3
• Polarizability: 25.711367 Å^3
• Polar Surface Area: 26.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.94
• LOG S: -1.01
• Solubility (Water): 2.25e+01 g/l

PROPERTIES

Physical Property

• Solubility: 54.4 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: 105-109°C; 107-109
• Hydrophobicity(logP): 1.00 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• Storage Warning: Air & Light Sensitive
• RTECS: CD2625000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22; 22-36/37/38; R:22
• Safety Statements: 26-36; 36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H302
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: Others

Product Information

• Purity: 98+%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02157785

Free Base
Crystalline

MP Biomedicals - 05214044

MP Biomedicals Rare Chemical collection

DrugBank - DB01424

• Drug Groups: approved; withdrawn
• Description: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]
• Indication: Formerly widely used as an antipyretic and analgesic in rheumatism, neuritis, and common colds. Currently used to measure total body water.
• Pharmacology: Aminophenazone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [Wikipedia]
• Toxicity: Can cause life-threatening agranulocytosis.
• Affected Organisms: Humans and other mammals
• References: Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - D8015

Biochem/physiol Actions
Antipyrine was found to be nonmutagenic when screened against Salmonella typhimurium tester strains TA100, TA98, TA97, TA102 and TA104.3
Application
Oxidation by Fe(VI) has potential to remove N-nitrosodimethylamine precursors, including 4-dimethylaminoantipyrine, from drinking water.1 4-Dimethylaminoantipyrine is itself an effective scavenger of reactive nitrogen compounds nitric oxide and peroxynitrite, important in the inflammatory response.2

REFERENCES

• Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. Pubmed