N-ethyl-N-(2-methylphenyl)but-2-enamide

• ChemBase ID: 150
• Molecular Formular: C13H17NO
• Molecular Mass: 203.28018
• Monoisotopic Mass: 203.13101417
• SMILES: O=C(N(c1c(cccc1)C)CC)C=CC
• Canonical SMILES: CC=CC(=O)N(c1ccccc1C)CC
• InChI: InChI=1S/C13H17NO/c1-4-8-13(15)14(5-2)12-10-7-6-9-11(12)3/h4,6-10H,5H2,1-3H3
• InChIKey: DNTGGZPQPQTDQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-ethyl-N-(2-methylphenyl)but-2-enamide; (2E)-N-ethyl-N-(2-methylphenyl)but-2-enamide
• IUPAC Traditional name: eurax; crotamitonum; crotamiton
• Brand Name: Crotamitex; Crotan; Eurasil; Eurax; Eurax Cream; Eurax Lotion; Euraxil; Veteusan
• Synonyms: Crotamiton; N-Ethyl-o-crotonotoluidide; Crotamitone; Crotaglin; Crotalgin; Crotamiton; trans-Crotalgin; trans-Crotamitex; N-Ethyl-o-crotonotoluidide; trans-Crotamitone; Crotonyl N-ethyl-o-toluidine; trans-N-Crotonyl-N-ethyl-o-toluidine; (2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamide; trans-Crotamiton; 克罗米通; N-乙基-邻巴豆酰甲基苯胺

Database IDs

• CAS Number: 483-63-6; 124236-29-9
• EC Number: 207-596-3
• MDL Number: MFCD00026989
• PubChem SID: 24847834; 160963613; 46508599
• PubChem CID: 2883; 688020
• ATC CODE: QP53AX04
• CHEMBL: 1200709
• Chemspider ID: 599515
• DrugBank ID: DB00265
• KEGG ID: D01381
• Unique Ingredient Identifier: D6S4O4XD0H
• Wikipedia Title: Crotamiton

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.0881793
• LogD (pH = 7.4): 3.0881796
• Log P: 3.0881796
• Molar Refractivity: 64.1479 cm^3
• Polarizability: 24.114462 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.7
• LOG S: -2.76
• Solubility (Water): 3.53e-01 g/l

PROPERTIES

Physical Property

• Boiling Point: 153-155 °C/13 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 0.987 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.54(lit.)
• Hydrophobicity(logP): 2.9

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: GQ7000000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/38-43; R:22
• Safety Statements: 26-36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Pregnancy Category: C

Product Information

• Purity: 97%
• Description: predominantly trans
• Linear Formula: CH3CH=CHCON(C2H5)C6H4CH3

DETAILS

DrugBank - DB00265

• Drug Groups: approved
• Description: Crotamiton is a scabicidal and antipruritic agent available as a cream or lotion for topical use only. It is a colorless to slightly yellowish oil, having a faint amine-like odor. It is miscible with alcohol and with methanol.
• Indication: For eradication of scabies (Sarcoptes scabiei) and for symptomatic treatment of pruritic skin.
• Pharmacology: Crotamiton is usually used to treat pruritis (itching of the skin) caused by scabies or sunburn. Crotamiton relieves itching by producing what is called a counter-irritation. As crotamiton evaporates from the skin, it produces a cooling effect. This cooling effect helps to divert your body's attention away from the itching. Due to this cooling effect it is also effective for the relief of sunburn. The drug is also believed to kill scabies through an unknown mechanism.
• Affected Organisms: Humans and other mammals
• Absorption: 10 % absorbed when applied locally.
• References: Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 128201

Packaging
5 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 128201.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C818000

Crotamiton is an anti-parasitic agent. Crotamiton is used both as a scabicidal (for treating scabies) and as a general antipruritic.

REFERENCES

• Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. Pubmed
• Buffet, M. et al.: Fund. Clin. Pharmacol., 17, 217 (2003)
• Lemke, T.L.: Foye’s Prin. Med. Chem., 6, 1084 (2003)
• Dika, E. et al.: Cutan. Ocular Toxicol., 25, 211 (2003)