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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:50:25 UTC
Update Date2017-12-07 04:29:57 UTC
HMDB IDHMDB0041965
Secondary Accession Numbers
  • HMDB41965
Metabolite Identification
Common NameO-Toluidine
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.
Structure
Thumb
Synonyms
ValueSource
1-amino-2-MethylbenzeneChEBI
1-Methyl-2-aminobenzeneChEBI
2-amino-1-MethylbenzeneChEBI
2-AminotolueneChEBI
2-Methyl-1-aminobenzeneChEBI
2-MethylbenzamineChEBI
2-MethylbenzenamineChEBI
2-ToluidineChEBI
O-AminotolueneChEBI
O-MethylanilineChEBI
O-MethylbenzenamineChEBI
O-TolylamineChEBI
2-Methyl-anilineHMDB
2-Methyl-benzenamineHMDB
2-MethylanilineHMDB
2-Methylphenylamine (acd/name 4.0)HMDB
O-ToluideHMDB
O-ToluidinHMDB
O-Toluidine (acd/name 4.0)HMDB
O-ToluidynaHMDB
ortho-ToluidineHMDB
Rcra waste number u328HMDB
Chemical FormulaC7H9N
Average Molecular Weight107.1531
Monoisotopic Molecular Weight107.073499293
IUPAC Name2-methylaniline
Traditional Nametoluidine
CAS Registry Number95-53-4
SMILES
CC1=CC=CC=C1N
InChI Identifier
InChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3
InChI KeyRNVCVTLRINQCPJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Substituted aniline
  • Aniline
  • Primary aromatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Role

Indirect biological role:

Biological role:

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-16.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16.6 mg/mL at 25 °CNot Available
LogP1.32Not Available
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 Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-ee7fe6869533a6858f94View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-68480e71423ffd272f9dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-ee7fe6869533a6858f94View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-68480e71423ffd272f9dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7900000000-661d661a8df390a5081aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-052f-9500000000-1da8fd338a6e499f67b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e311b1811a6d3a59268aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1c57a6134b99aef82338View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1843caa3f26f243817ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e44d3c280fede3615b13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-3cd853f6114cba521a13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-b4d6fdb227e5b9621611View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-2900000000-2f6e21711a72ca0477a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4l-7900000000-c0f650fc70669757d0e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9400000000-bcd0a7b786b0217f655cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9100000000-4312ff484c74be498895View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-4e34b2af3ed0df18b3b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-8facfe25a950827aa822View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00kf-9000000000-978c9096a7e167a13bc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-59dad1d5d1802381bc6aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-31d6e4c02cb1c35d7e2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-ee83d5d19af792cc8783View in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4faf1f04148279e9331aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4b5d5bc4707cf980910eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-a715018533d6dc4e8052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-0370f837fa70b324ecfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-9000000000-f0196e420945b736f49bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-1000f1353d3e835b7498View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3b8b19ef01e3a1cb8a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-aecf80c0988d8154d1e9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-5900000000-f04208345695340d7d9fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004550
KNApSAcK IDNot Available
Chemspider ID13854136
KEGG Compound IDC14403
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkToluidine
METLIN IDNot Available
PubChem Compound7242
PDB IDNot Available
ChEBI ID66892
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed: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. [PubMed:540633 ]
  3. Oganov RG, Aleksandrov AA, Vinogradova IV: [Sensitivity to insulin in acute myocardial infarct]. Kardiologiia. 1977 Jan;17(1):89-94. [PubMed:857071 ]
  4. Preece MA, Newall RG: Dextrostix-Eyetone in the insulin hypoglycaemia test. Br Med J. 1977 Jul 16;2(6080):152-4. [PubMed: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. [PubMed:949848 ]
  6. Briggs TB, Smith RR: Exertional rhabdomyolysis associated with decerebrate posturing. Neurosurgery. 1986 Aug;19(2):297-9. [PubMed:3748364 ]
  7. Akmal M, Massry SG: Peripheral nerve damage in patients with nontraumatic rhabdomyolysis. Arch Intern Med. 1983 Apr;143(4):835-6. [PubMed:6301396 ]
  8. Schulze VE Jr: Rhabdomyolysis as a cause of acute renal failure. Postgrad Med. 1982 Dec;72(6):145-7, 150-8. [PubMed:7145778 ]
  9. Ralph D: Rhabdomyolysis and acute renal failure. JACEP. 1978 Mar;7(3):103-6. [PubMed: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. [PubMed: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. [PubMed:8219998 ]
  12. Line RL, Rust GS: Acute exertional rhabdomyolysis. Am Fam Physician. 1995 Aug;52(2):502-6. [PubMed: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. [PubMed:7394218 ]
  14. Milne CJ: Rhabdomyolysis, myoglobinuria and exercise. Sports Med. 1988 Aug;6(2):93-106. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:1230533 ]