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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:52:52 UTC
Update Date2019-07-23 06:35:21 UTC
HMDB IDHMDB0042008
Secondary Accession Numbers
  • HMDB42008
Metabolite Identification
Common NameRitalinic acid
DescriptionRitalinic acid, also known as ritalinate, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Ritalinic acid is a very strong basic compound (based on its pKa). These are amino acids having a (-NH2) group attached to the beta carbon atom.
Structure
Data?1563863721
Synonyms
ValueSource
alpha-Phenyl-2-piperidineacetic acidChEBI
a-Phenyl-2-piperidineacetateGenerator
a-Phenyl-2-piperidineacetic acidGenerator
alpha-Phenyl-2-piperidineacetateGenerator
Α-phenyl-2-piperidineacetateGenerator
Α-phenyl-2-piperidineacetic acidGenerator
RitalinateGenerator
Ritalinic acid, (r*,r*)-(+-)-isomerHMDB
Chemical FormulaC13H17NO2
Average Molecular Weight219.2796
Monoisotopic Molecular Weight219.125928793
IUPAC Name2-phenyl-2-(piperidin-2-yl)acetic acid
Traditional Namephenyl(piperidin-2-yl)acetic acid
CAS Registry Number19395-41-6
SMILES
OC(=O)C(C1CCCCN1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C13H17NO2/c15-13(16)12(10-6-2-1-3-7-10)11-8-4-5-9-14-11/h1-3,6-7,11-12,14H,4-5,8-9H2,(H,15,16)
InChI KeyINGSNVSERUZOAK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP-0.32ALOGPS
logP-0.36ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)10.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.96 m³·mol⁻¹ChemAxon
Polarizability23.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9300000000-dc71fffe4d675962db98Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9520000000-ab57a14766f106dcb1b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-5349879fc5f8fc76b391Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-95b28a43f0777e9401baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-2cd3ebd39ba590055567Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-5349879fc5f8fc76b391Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-075b4840fbe857e8ccd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-210f28bbecb4977a5c73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0090000000-000b03fadb8e0e2d157fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-2090000000-bd71fa6fb9aa28c3acbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9030000000-c0a3a1f5012bbceaa097Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-95395a90021329c45c72Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-6fe94992bc8c559c4637Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-73161376dc9cb328306eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0090000000-e7f25e818947f99330e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-2090000000-2ca8b1684e34e53b75e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9020000000-2c2191b99d6ac20c55fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-d71faf730653bf91a556Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-77b8b619d738c3b695a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-de04d59769d400990721Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-aa4185502c8a9a60efaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1390000000-048fb36cd4edbad95c33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl0-6960000000-9328f8392654359c6eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-9400000000-8ae7fa901297e62a7518Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0970000000-1096f4480c2201e7f4a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2910000000-662a13b5c79c77499c05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9500000000-c47bd04961e3ff01ba1cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID78360
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkRitalinic acid
      METLIN IDNot Available
      PubChem Compound86863
      PDB IDNot Available
      ChEBI ID83481
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Paterson SM, Moore GA, Florkowski CM, George PM: Determination of methylphenidate and its metabolite ritalinic acid in urine by liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jan 15;881-882:20-6. doi: 10.1016/j.jchromb.2011.11.007. Epub 2011 Nov 28. [PubMed:22204874 ]
      2. Beck O, Stephanson N, Sandqvist S, Franck J: Determination of amphetamine and methylphenidate in exhaled breath of patients undergoing attention-deficit/hyperactivity disorder treatment. Ther Drug Monit. 2014 Aug;36(4):528-34. doi: 10.1097/FTD.0000000000000046. [PubMed:24452069 ]
      3. Gahr M, Kolle MA: Methylphenidate intoxication: somnolence as an uncommon clinical symptom and proof of overdosing by increased serum levels of ritalinic acid. Pharmacopsychiatry. 2014 Sep;47(6):215-8. doi: 10.1055/s-0034-1387700. Epub 2014 Aug 14. [PubMed:25121992 ]