ContaminantDB: crotamiton

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 05:01:18 UTC

Update Date

2016-11-09 01:15:16 UTC

Accession Number

CHEM015737

Identification

Common Name

crotamiton

Class

Small Molecule

Description

An enamide resulting from the formal condensation of crotonic acid with N-ethyl-2-methylaniline. A colourless or pale yellow oily liquid, it is used in the treatment of pruritus (itching) by producing a counter-irritation: as it evaporates from the skin, it produces a cooling effect that diverts attention away from the itching. It has also been used as an acaricide in the treatment of scabies, though more effective drugs are usually preferred.

Contaminant Sources

HMDB Contaminants - Urine
OECD HPV Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Crotalgin	ChEBI
Crotamitone	ChEBI
Crotamitonum	ChEBI
Crotonyl-N-ethyl-O-toluidine	ChEBI
N-Ethyl-O-crotonotoluidide	ChEBI
Crotaglin	HMDB

Chemical Formula

C₁₃H₁₇NO

Average Molecular Mass

203.280 g/mol

Monoisotopic Mass

203.131 g/mol

CAS Registry Number

483-63-6

IUPAC Name

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

Traditional Name

eurax

SMILES

CCN(C(=O)C=CC)C1=CC=CC=C1C

InChI Identifier

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

InChI Key

DNTGGZPQPQTDQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Toluene
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enamide (CHEBI:31439 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	2.7	ALOGPS
logP	3.09	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-0.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.15 m³·mol⁻¹	ChemAxon
Polarizability	23.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bl-5900000000-f2f8a0d107e489eb71dd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0090000000-70e1ca34f13b9e4b9599	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-1190000000-02218095d009d51f0b72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-9850000000-24da05acdd172bfde5f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9700000000-ae61a473efc6d72b8781	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9600000000-6aaa881b4c06e68ed133	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9500000000-27cbd5bf3c121b56d6cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-066u-9400000000-12ca412deed8c16a0f22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-066u-9300000000-427f77529d09e1395f78	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-066u-9200000000-a03907e2130c0b4a1530	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-9300000000-0525b5898c1d28deecf8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-1190000000-fa6a77b2381b31ef15d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0090000000-0be9e4200f38f97b043a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-9500000000-28fad8d7453a88c6e11b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-9400000000-7e8a2792944657879e6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014i-9600000000-01363ad732d1dc8b0b38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0gb9-9850000000-097983eff18404ea2ba6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-9300000000-dfe4b394f5773013a6cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-9400000000-5f5d5be9b48d6924bf57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 120V, Positive	splash10-066u-9400000000-fcab39711ba6b360fca6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1490000000-00153d7c4df5e973fbf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-5940000000-afaa79fe171dc4f62c29	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8900000000-7379d2bd22a49c6f4d9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0190000000-4eb068c92e31c2951f1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ul0-4930000000-7ea235dd883e82f45391	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pwc-6900000000-67fa77a6e735397d1a5d	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00265

HMDB ID

HMDB0014410

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25.

crotamiton (CHEM015737)

Structure for CHEM015737: crotamiton