O-Toluidine (T3D4217)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-08-29 05:53:47 UTC
Update Date2014-12-24 20:26:42 UTC
Accession NumberT3D4217
Identification
Common NameO-Toluidine
ClassSmall Molecule
DescriptionThe chemical properties of the toluidines are quite similar to those of aniline and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic. None of the toluidines is very soluble in pure water, but will become soluble if the aqueous solution is acidic due to formation of ammonium salts, as usual for organic amines. At room temperature and pressure, ortho- and meta-toluidines are viscous liquids, but para-toluidine is a flaky solid. This can be explained by the fact that the p-toluidine molecules are more symmetrical and fit into a crystalline structure more easily. p-Toluidine can be obtained from reduction of p-nitrotoluene. p-Toluidine reacts with formaldehyde to form Troger's base.
Compound Type
  • Amine
  • Cigarette Toxin
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Amino-2-methylbenzene
1-Methyl-2-aminobenzene
2-Amino-1-methylbenzene
2-Aminotoluene
2-Methyl-1-aminobenzene
2-Methyl-Aniline
2-Methyl-Benzenamine
2-Methylaniline
2-Methylbenzenamine
2-Methylphenylamine
2-Toluidine
O-Aminotoluene
O-Methylaniline
O-Methylbenzenamine
O-Toluide
O-Toluidin
O-Toluidyna
O-Tolylamine
Ortho-Toluidine
Rcra waste number U328
Chemical FormulaC7H9N
Average Molecular Mass107.153 g/mol
Monoisotopic Mass107.073 g/mol
CAS Registry Number95-53-4
IUPAC Name2-methylaniline
Traditional Nametoluidine
SMILESCC1=CC=CC=C1N
InChI IdentifierInChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3
InChI KeyInChIKey=RNVCVTLRINQCPJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentAminotoluenes
Alternative Parents
Substituents
  • Aminotoluene
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-16.3°C
Boiling PointNot Available
Solubility16.6 mg/mL at 25°C
LogP1.32
Predicted Properties
PropertyValueSource
Water Solubility10.8 g/LALOGPS
logP1.32ALOGPS
logP1.66ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)4.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.8 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-ee7fe6869533a6858f942017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-68480e71423ffd272f9d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-ee7fe6869533a6858f942018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-68480e71423ffd272f9d2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7900000000-661d661a8df390a5081a2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-052f-9500000000-1da8fd338a6e499f67b82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e311b1811a6d3a59268a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1c57a6134b99aef823382017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1843caa3f26f243817eb2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e44d3c280fede3615b132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-3cd853f6114cba521a132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-b4d6fdb227e5b96216112017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-2900000000-2f6e21711a72ca0477a82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4l-7900000000-c0f650fc70669757d0e62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9400000000-bcd0a7b786b0217f655c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9100000000-4312ff484c74be4988952017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-4e34b2af3ed0df18b3b22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-8facfe25a950827aa8222017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00kf-9000000000-978c9096a7e167a13bc32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-59dad1d5d1802381bc6a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-31d6e4c02cb1c35d7e2d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-ee83d5d19af792cc87832017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4faf1f04148279e9331a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4b5d5bc4707cf980910e2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-a715018533d6dc4e80522015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-0370f837fa70b324ecfe2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-9000000000-f0196e420945b736f49b2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-1000f1353d3e835b74982015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3b8b19ef01e3a1cb8a0d2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-aecf80c0988d8154d1e92015-04-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-5900000000-f04208345695340d7d9f2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (21)
Uses/SourcesThis is a toxic chemical found in cigarettes or generated by tobacco combustion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41965
PubChem Compound ID7242
ChEMBL IDCHEMBL1381
ChemSpider ID13854136
KEGG IDC14403
UniProt IDNot Available
OMIM ID
ChEBI ID66892
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia Linko-toluidine
References
Synthesis ReferenceNot Available
MSDST3D4217.pdf
General References
  1. Lawson NS, Haven GT, Moore TD: Long-term stability of glucose in lyophilized quality control serum. A study utilizing data from the Quality Assurance Service (QAS) Program of the College of American Pathologists. Am J Clin Pathol. 1978 Sep;70(3 Suppl):523-31. [707419 ]
  2. Roberts MC, Norman P: A re-evaluation of the D (+) xylose absorption test in the horse. Equine Vet J. 1979 Oct;11(4):239-43. [540633 ]
  3. Oganov RG, Aleksandrov AA, Vinogradova IV: [Sensitivity to insulin in acute myocardial infarct]. Kardiologiia. 1977 Jan;17(1):89-94. [857071 ]
  4. Preece MA, Newall RG: Dextrostix-Eyetone in the insulin hypoglycaemia test. Br Med J. 1977 Jul 16;2(6080):152-4. [871822 ]
  5. Kiang SW, Kuan JW, Kuan SS, Guilbault GG: Measurement of glucose in plasma, with use of immobilized glucose oxidase and peroxidase. Clin Chem. 1976 Aug;22(8):1378-82. [949848 ]
  6. Briggs TB, Smith RR: Exertional rhabdomyolysis associated with decerebrate posturing. Neurosurgery. 1986 Aug;19(2):297-9. [3748364 ]
  7. Akmal M, Massry SG: Peripheral nerve damage in patients with nontraumatic rhabdomyolysis. Arch Intern Med. 1983 Apr;143(4):835-6. [6301396 ]
  8. Schulze VE Jr: Rhabdomyolysis as a cause of acute renal failure. Postgrad Med. 1982 Dec;72(6):145-7, 150-8. [7145778 ]
  9. Ralph D: Rhabdomyolysis and acute renal failure. JACEP. 1978 Mar;7(3):103-6. [633672 ]
  10. Yasunaga Y, Nakanishi H, Naka N, Miki T, Tsujimura T, Itatani H, Okuyama A, Aozasa K: Alterations of the p53 gene in occupational bladder cancer in workers exposed to aromatic amines. Lab Invest. 1997 Dec;77(6):677-84. [9426406 ]
  11. Viner BM, Kisel' VL, Krendal' FP, Rubtsova ER: [A modification of the ortho-toluidine method for determining glucose in the blood]. Eksp Klin Farmakol. 1993 May-Jun;56(3):62-4. [8219998 ]
  12. Line RL, Rust GS: Acute exertional rhabdomyolysis. Am Fam Physician. 1995 Aug;52(2):502-6. [7625324 ]
  13. De La Morena Garcia E, Garcia Lomas Pico LA, Salas Salas FJ, Cantero Garcia-Arenal L: [Comparison of the blood glucose levels obtained by the Reflomat-Glucose-Reflotest and the orthotoluidine method]. Rev Clin Esp. 1980 Mar 31;156(6):403-5. [7394218 ]
  14. Milne CJ: Rhabdomyolysis, myoglobinuria and exercise. Sports Med. 1988 Aug;6(2):93-106. [3062736 ]
  15. Sefer S, Degoricija V, Bilic B, Trotic R, Milanovic-Stipkovic B, Ratkovi-Gusic I, Kes P: Acute carbon monoxide poisoning as the cause of rhabdomyolysis and acute renal failure. Acta Med Croatica. 1999;53(4-5):199-202. [10914136 ]
  16. Tkaczewski W, Chojnacki J, Bogoniowska Z: The effect of glucagon on the blood levels of gastrin, insulin and glucose in patients with gastric and duodenal ulcers. Acta Hepatogastroenterol (Stuttg). 1979 Oct;26(5):396-8. [525217 ]
  17. Klimek K, Gdakowicz B, Gregorczyk J: [Ability of the tissues to assimilate glucose and the pyruvate and lactate levels after intravenous glucose load in patients with peripheral facial paralysis]. Neurol Neurochir Pol. 1985 Sep-Oct;19(5):395-400. [3831793 ]
  18. Polushina ND: [The effect of mineral water on serotonin and insulin production (an experimental study)]. Vopr Kurortol Fizioter Lech Fiz Kult. 1998 Jul-Aug;(4):9-10. [9855765 ]
  19. Varkonyi T, Balint GA, Csati S, Varro V: Laboratory method for measuring small amounts of tissue glycogen. Biochem Exp Biol. 1980;16(2):175-9. [7348198 ]
  20. Oganov RG, Aleksandrov AA, Vinogradova NV, Korochkin IM: [Content of immunoreactive insulin and catecholamines in blood plasma and disorders of carbohydrate metabolism in patients with myocardial infarct]. Kardiologiia. 1975 Sep;15(9):91-100. [1230533 ]
  21. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Nuclear receptor subfamily 1 group I member 2
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.24 uMNVS_NR_hPXRNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]