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Record Information
StatusExpected but not Quantified
Creation Date2012-09-13 11:50:25 UTC
Update Date2019-07-23 06:35:18 UTC
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.
2-Methylphenylamine (acd/name 4.0)HMDB
O-Toluidine (acd/name 4.0)HMDB
Rcra waste number u328HMDB
Chemical FormulaC7H9N
Average Molecular Weight107.1531
Monoisotopic Molecular Weight107.073499293
IUPAC Name2-methylaniline
Traditional Nametoluidine
CAS Registry Number95-53-4
InChI Identifier
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
  • Aminotoluene
  • Substituted aniline
  • Aniline
  • Primary aromatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physiological effect

Health effect:




Indirect biological role:

Biological role:

Environmental role:

Physical Properties
Experimental Properties
Melting Point-16.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16.6 mg/mL at 25 °CNot Available
LogP1.32Not Available
Predicted Properties
Water Solubility10.8 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-ee7fe6869533a6858f94JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-68480e71423ffd272f9dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-ee7fe6869533a6858f94JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-68480e71423ffd272f9dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7900000000-661d661a8df390a5081aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-052f-9500000000-1da8fd338a6e499f67b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e311b1811a6d3a59268aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1c57a6134b99aef82338JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1843caa3f26f243817ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e44d3c280fede3615b13JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-3cd853f6114cba521a13JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-b4d6fdb227e5b9621611JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-2900000000-2f6e21711a72ca0477a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4l-7900000000-c0f650fc70669757d0e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9400000000-bcd0a7b786b0217f655cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9100000000-4312ff484c74be498895JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-4e34b2af3ed0df18b3b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-8facfe25a950827aa822JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00kf-9000000000-978c9096a7e167a13bc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-59dad1d5d1802381bc6aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-31d6e4c02cb1c35d7e2dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-ee83d5d19af792cc8783JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4faf1f04148279e9331aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4b5d5bc4707cf980910eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-a715018533d6dc4e8052JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-0370f837fa70b324ecfeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-9000000000-f0196e420945b736f49bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-1000f1353d3e835b7498JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3b8b19ef01e3a1cb8a0dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-aecf80c0988d8154d1e9JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-5900000000-f04208345695340d7d9fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  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 ]
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  6. Briggs TB, Smith RR: Exertional rhabdomyolysis associated with decerebrate posturing. Neurosurgery. 1986 Aug;19(2):297-9. [PubMed:3748364 ]
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  9. Ralph D: Rhabdomyolysis and acute renal failure. JACEP. 1978 Mar;7(3):103-6. [PubMed:633672 ]
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  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 ]