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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-13 01:15:23 UTC
HMDB IDHMDB00118
Secondary Accession Numbers
  • HMDB04285
Metabolite Identification
Common NameHomovanillic acid
DescriptionHomovanillic acid is a dopamine metabolite occurring in human biofluids. A high proportion of patients with neuroblastoma excrete increased amounts of it in their urine. Homovanillic acid is a major catecholamine metabolite. It is used as a reagent to detect oxidative enzymes.(Wikipedia).
Structure
Thumb
Synonyms
  1. (4-Hydroxy-3-methoxyphenyl)acetate
  2. (4-Hydroxy-3-methoxyphenyl)acetic acid
  3. 3-Methoxy-4-hydroxy-phenylacetic acid
  4. 3-Methoxy-4-hydroxyphenylacetate
  5. 3-Methoxy-4-hydroxyphenylacetic acid
  6. 4-hydroxy 3-methoxyphenylacetic acid
  7. 4-Hydroxy-3-methoxybenzeneacetate
  8. 4-Hydroxy-3-methoxybenzeneacetic acid
  9. 4-Hydroxy-3-methoxyphenylacetic acid
  10. Homovanilate
  11. Homovanilic acid
  12. Homovanillate
  13. Homovanillinic acid
  14. Vanilacetate
  15. Vanilacetic acid
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional IUPAC Namehomovanillic acid
CAS Registry Number306-08-1
SMILES
COC1=CC(CC(O)=O)=CC=C1O
InChI Identifier
InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChI KeyQRMZSPFSDQBLIX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassTyrosols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • aromatic ether(ChEBI)
  • monocarboxylic acid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Carboxylic Acid
  • Methoxyphenol
  • Phenylacetate
Direct ParentTyrosols and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17 mg/mLNot Available
LogP0.33LAHANN,TR ET AL. (1989)
Predicted Properties
PropertyValueSource
water solubility2.72 g/LALOGPS
logP1.02ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (strongest acidic)3.74ChemAxon
pKa (strongest basic)-4.9ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area66.76ChemAxon
rotatable bond count3ChemAxon
refractivity45.81ChemAxon
polarizability17.74ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Caudate Nucleus
  • Central Nervous System
  • Fibroblasts
  • Kidney
  • Spinal Cord
  • Striatum
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.082 +/- 0.050 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.048 +/- 0.009 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.03 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.047 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.078 +/- 0.029 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.029 +/- 0.045 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.027 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.029 +/- 0.005 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.166 +/- 0.147 uMAdult (>18 years old)Male
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.574 (0.302-0.845) uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1521 +/- 0.0177 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.658-1.434 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.324-1.098 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.105-0.262 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.33-0.668 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.346-0.716 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 +/- 0.07 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.19+/- 0.093 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.28 (0.15-0.41) uMAdolescent (13-18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0004 +/- 0.00006 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.89 +/- 0.47 uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.78 +/- 0.42 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.76 +/- 0.38 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.71 +/- 0.34 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.66 +/- 0.33 uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.66 +/- 0.48 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.54 +/- 0.211 uMAdolescent (13-18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.37 +/- 0.08 uMAdolescent (13-18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.14 +/- 0.54 uMNewborn (0-30 days old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.14 +/- 0.046 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.40 +/- 0.075 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.039 +/- 0.021 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.174 +/- 0.075 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.202 +/- 0.094 uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.94 +/- 0.11 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.384-0.765 uMChildren (1-13 years old)Not Specifiednormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.401 +/- 0.188 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.20 (0.047-0.35) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.26 +/- 1.58 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified4.93 +/-3.37 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified10.5 (2.0-19.0) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified17.1 (7.1-28.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified20.6 (15.6-31.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified7.5 (3.6-14.6) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified5.6 (2.1-47.3) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<=3.618 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified6.2 (1.8-12.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.3 (0.9-5.5) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.2 (0.4-4.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified10.9 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.133 +/- 0.015 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified4.3 (0.9-8.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.062 +/- 0.022 uMAdult (>18 years old)MaleSchizophrenia details
BloodDetected and Quantified0.071 +/- 0.022 uMAdult (>18 years old)FemaleSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.39773 (0.155-0.654) uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.083 +/- 0.000 uMInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1347 +/- 0.0121 uMAdult (>18 years old)Not SpecifiedParkinson's syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified0.654 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.155 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.292 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.49 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.49 +/- 0.08 uMChildren (1-13 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.39 +/- 0.091 uMAdult (>18 years old)Not SpecifiedNarcolepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.21 +/- 0.08 uMAdult (>18 years old)Not SpecifiedGrowth hormone deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.21 +/- 0.035 uMAdult (>18 years old)FemaleSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.19 +/- 0.030 uMAdult (>18 years old)FemaleSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.2572 +/- 0.1055 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.229 +/- 0.0782 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
Cerebrospinal Fluid (CSF)Detected and Quantified0.21 +/- 0.12 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.05 +/- 0.03 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.05 +/- 0.04 uMAdult (>18 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.19 +/- 0.09 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.20 +/- 0.09 uMAdult (>18 years old)Both
Major depression
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.17 +/- 0.084 uMAdult (>18 years old)Not SpecifiedPanic Disorder details
Cerebrospinal Fluid (CSF)Detected and Quantified0.16 +/- 0.095 uMElderly (>65 years old)Not SpecifiedParkinson's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.17 +/- 0.01 uMAdult (>18 years old)Not SpecifiedOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.17 +/- 0.01 uMNot SpecifiedNot SpecifiedFriedreich's ataxia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.15 +/- 0.03 uMAdult (>18 years old)Not SpecifiedAutosomal recessive spastic ataxia of Charlevoix-Saguena details
Cerebrospinal Fluid (CSF)Detected and Quantified0.50 +/- 0.32 uMChildren (1-13 years old)Not SpecifiedAutism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0002 +/- 0.00005 uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00137 (0.000604-0.00225) uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.038 +/- 0.016 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00017 (0.00013-0.00022) uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1282 +/- 0.0583 uMNot SpecifiedBothceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0585 (0.055-0.062) uMChildren (1-13 years old)Not Specifiedsepiapterin reductase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.187 +/- 0.065 uMAdult (>18 years old)Not SpecifiedParkinson's Disease details
UrineDetected and Quantified2.9 +/- 0.0 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  1. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. Pubmed: 16288991
Autism
  1. Narayan M, Srinath S, Anderson GM, Meundi DB: Cerebrospinal fluid levels of homovanillic acid and 5-hydroxyindoleacetic acid in autism. Biol Psychiatry. 1993 Apr 15-May 1;33(8-9):630-5. Pubmed: 7687150
Major depressive disorder
  1. Sheline Y, Bardgett ME, Csernansky JG: Correlated reductions in cerebrospinal fluid 5-HIAA and MHPG concentrations after treatment with selective serotonin reuptake inhibitors. J Clin Psychopharmacol. 1997 Feb;17(1):11-4. Pubmed: 9004051
Epilepsy
  1. Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. Pubmed: 1705463
  2. Shaywitz BA, Cohen DJ, Bowers MB: Reduced cerebrospinal fluid 5-hydroxyindoleacetic acid and homovanillic acid in children with epilepsy. Neurology. 1975 Jan;25(1):72-9. Pubmed: 803305
Schizophrenia
  1. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. Pubmed: 2480613
  2. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563
  3. Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. Pubmed: 115032
Friedreich's ataxia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
Growth hormone deficiency
  1. Burman P, Hetta J, Wide L, Mansson JE, Ekman R, Karlsson FA: Growth hormone treatment affects brain neurotransmitters and thyroxine [see comment] Clin Endocrinol (Oxf). 1996 Mar;44(3):319-24. Pubmed: 8729530
Hypothyroidism
  1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
Narcolepsy
  1. Strittmatter M, Isenberg E, Grauer MT, Hamann G, Schimrigk K: CSF substance P somatostatin and monoaminergic transmitter metabolites in patients with narcolepsy. Neurosci Lett. 1996 Nov 1;218(2):99-102. Pubmed: 8945737
Olivopontocerebral atrophy
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
Panic disorder
  1. Eriksson E, Westberg P, Alling C, Thuresson K, Modigh K: Cerebrospinal fluid levels of monoamine metabolites in panic disorder. Psychiatry Res. 1991 Mar;36(3):243-51. Pubmed: 1712114
Parkinson's disease
  1. LeWitt PA, Galloway MP, Matson W, Milbury P, McDermott M, Srivastava DK, Oakes D: Markers of dopamine metabolism in Parkinson's disease. The Parkinson Study Group. Neurology. 1992 Nov;42(11):2111-7. Pubmed: 1436520
Hereditary spastic paraplegia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID574
Phenol Explorer Metabolite ID574
FoodDB IDFDB001783
KNApSAcK IDC00029504
Chemspider ID1675
KEGG Compound IDC05582
BioCyc IDNot Available
BiGG ID46066
Wikipedia LinkHomovanillic acid
NuGOwiki LinkHMDB00118
Metagene LinkHMDB00118
METLIN ID971
PubChem Compound1738
PDB IDNot Available
ChEBI ID545959
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  3. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. Pubmed: 12649306
  4. Hyland K, Gunasekara RS, Munk-Martin TL, Arnold LA, Engle T: The hph-1 mouse: a model for dominantly inherited GTP-cyclohydrolase deficiency. Ann Neurol. 2003;54 Suppl 6:S46-8. Pubmed: 12891653
  5. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. Pubmed: 9849813
  6. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. Pubmed: 8884658
  7. Needlman R, Zuckerman B, Anderson GM, Mirochnick M, Cohen DJ: Cerebrospinal fluid monoamine precursors and metabolites in human neonates following in utero cocaine exposure: a preliminary study. Pediatrics. 1993 Jul;92(1):55-60. Pubmed: 8516085
  8. Houston JP, Maas JW, Bowden CL, Contreras SA, McIntyre KL, Javors MA: Cerebrospinal fluid HVA, central brain atrophy, and clinical state in schizophrenia. Psychiatry Res. 1986 Nov;19(3):207-14. Pubmed: 3797547
  9. Scatton B, Dennis T, L'Heureux R, Monfort JC, Duyckaerts C, Javoy-Agid F: Degeneration of noradrenergic and serotonergic but not dopaminergic neurones in the lumbar spinal cord of parkinsonian patients. Brain Res. 1986 Aug 13;380(1):181-5. Pubmed: 2428421
  10. Javors MA, Bowden CL, Maas JW: 3-methoxy-4-hydroxyphenylglycol, 5-hydroxyindoleacetic acid, and homovanillic acid in human cerebrospinal fluid. Storage and measurement by reversed-phase high-performance liquid chromatography and coulometric detection using 3-methoxy-4-hydroxyphenyllactic acid as an internal standard. J Chromatogr. 1984 Dec 12;336(2):259-69. Pubmed: 6085084
  11. Court JA, Lloyd S, Thomas N, Piggott MA, Marshall EF, Morris CM, Lamb H, Perry RH, Johnson M, Perry EK: Dopamine and nicotinic receptor binding and the levels of dopamine and homovanillic acid in human brain related to tobacco use. Neuroscience. 1998 Nov;87(1):63-78. Pubmed: 9722142
  12. Reynolds GP, Garrett NJ: Striatal dopamine and homovanillic acid in Huntington's disease. J Neural Transm. 1986;65(2):151-5. Pubmed: 2939198
  13. Kay AD, Schapiro MB, Riker AK, Haxby JV, Rapoport SI, Cutler NR: Cerebrospinal fluid monoaminergic metabolites are elevated in adults with Down's syndrome. Ann Neurol. 1987 Apr;21(4):408-11. Pubmed: 2437853
  14. Lovenberg W, Levine RA, Robinson DS, Ebert M, Williams AC, Calne DB: Hydroxylase cofactor activity in cerebrospinal fluid of normal subjects and patients with Parkinson's disease. Science. 1979 May 11;204(4393):624-6. Pubmed: 432666
  15. Ruberg M, Javoy-Agid F, Hirsch E, Scatton B, LHeureux R, Hauw JJ, Duyckaerts C, Gray F, Morel-Maroger A, Rascol A, et al.: Dopaminergic and cholinergic lesions in progressive supranuclear palsy. Ann Neurol. 1985 Nov;18(5):523-9. Pubmed: 3000280
  16. Kaminski R, Powchick P, Warne PA, Goldstein M, McQueeney RT, Davidson M: Measurement of plasma homovanillic acid concentrations in schizophrenic patients. Prog Neuropsychopharmacol Biol Psychiatry. 1990;14(3):271-87. Pubmed: 2193315
  17. Birkmayer W, Birkmayer GJ: Nicotinamidadenindinucleotide (NADH): the new approach in the therapy of Parkinson's disease. Ann Clin Lab Sci. 1989 Jan-Feb;19(1):38-43. Pubmed: 2644889
  18. Lambert GW, Eisenhofer G, Jennings GL, Esler MD: Regional homovanillic acid production in humans. Life Sci. 1993;53(1):63-75. Pubmed: 8515683
  19. Pifl C, Schingnitz G, Hornykiewicz O: The neurotoxin MPTP does not reproduce in the rhesus monkey the interregional pattern of striatal dopamine loss typical of human idiopathic Parkinson's disease. Neurosci Lett. 1988 Oct 5;92(2):228-33. Pubmed: 3263594
  20. Grant DB, Dunger DB, Smith I, Hyland K: Familial glucocorticoid deficiency with achalasia of the cardia associated with mixed neuropathy, long-tract degeneration and mild dementia. Eur J Pediatr. 1992 Feb;151(2):85-9. Pubmed: 1537368
  21. Eriksson E, Westberg P, Alling C, Thuresson K, Modigh K: Cerebrospinal fluid levels of monoamine metabolites in panic disorder. Psychiatry Res. 1991 Mar;36(3):243-51. Pubmed: 1712114
  22. Lepore V, Di Reda N, Defazio G, Pedone D, Giovine A, Lanzi C, Tartaglione B, Livrea P: Dopaminomimetic action of diphenylhydantoin in rat striatum: effect on homovanillic acid and cyclic AMP levels. Psychopharmacology (Berl). 1985;86(1-2):27-30. Pubmed: 2991966
  23. Levreri I, Caruso U, Deiana F, Buoncompagni A, De Bernardi B, Marchese N, Melioli G: The secretion of ibuprofen metabolites interferes with the capillary chromatography of urinary homovanillic acid and 4-hydroxy-3-methoxymandelic acid in neuroblastoma diagnosis. Clin Chem Lab Med. 2005;43(2):173-7. Pubmed: 15843212
  24. Broderick PA, Barr GA, Sharpless NS, Bridger WH: Biogenic amine alterations in limbic brain regions of muricidal rats. Res Commun Chem Pathol Pharmacol. 1985 Apr;48(1):3-15. Pubmed: 2581293
  25. Sullivan GM, Oquendo MA, Huang YY, Mann JJ: Elevated cerebrospinal fluid 5-hydroxyindoleacetic acid levels in women with comorbid depression and panic disorder. Int J Neuropsychopharmacol. 2006 Oct;9(5):547-56. Epub 2005 Nov 1. Pubmed: 16259647
  26. Lekman A, Witt-Engerstrom I, Gottfries J, Hagberg BA, Percy AK, Svennerholm L: Rett syndrome: biogenic amines and metabolites in postmortem brain. Pediatr Neurol. 1989 Nov-Dec;5(6):357-62. Pubmed: 2604799
  27. Losonczy MF, Song IS, Mohs RC, Mathe AA, Davidson M, Davis BM, Davis KL: Correlates of lateral ventricular size in chronic schizophrenia, II: biological measures. Am J Psychiatry. 1986 Sep;143(9):1113-8. Pubmed: 2428259
  28. Seeldrayers P, Messina D, Desmedt D, Dalesio O, Hildebrand J: CSF levels of neurotransmitters in Alzheimer-type dementia. Effects of ergoloid mesylate. Acta Neurol Scand. 1985 May;71(5):411-4. Pubmed: 2409733
  29. Lembreghts M, Ansseau M: [Biological markers in schizophrenia] Encephale. 1993 Sep-Oct;19(5):501-23. Pubmed: 8306920
  30. Dale G, McGill AC, Seviour JA, Craft AW: Urinary excretion of HMMA and HVA in infants. Ann Clin Biochem. 1988 May;25 ( Pt 3):233-6. Pubmed: 3400977
  31. Sardar AM, Czudek C, Reynolds GP: Dopamine deficits in the brain: the neurochemical basis of parkinsonian symptoms in AIDS. Neuroreport. 1996 Mar 22;7(4):910-2. Pubmed: 8724671
  32. Ormazabal A, Garcia-Cazorla A, Fernandez Y, Fernandez-Alvarez E, Campistol J, Artuch R: HPLC with electrochemical and fluorescence detection procedures for the diagnosis of inborn errors of biogenic amines and pterins. J Neurosci Methods. 2005 Mar 15;142(1):153-8. Pubmed: 15652629
  33. Ali SF, Kordsmeier KJ, Gough B: Drug-induced circling preference in rats. Correlation with monoamine levels. Mol Neurobiol. 1995 Aug-Dec;11(1-3):145-54. Pubmed: 8561958
  34. von Holst H, Lindquist C, Sedvall G: Increased concentrations of the monoamine metabolites homovanillic acid and 5-hydroxyindoleacetic acid in lumbar and central CSF and of 3-methoxy-4-hydroxyphenylglycol in lumbar CSF after subarachnoid haemorrhage. Acta Neurochir (Wien). 1985;77(3-4):146-51. Pubmed: 2416192
  35. Strittmatter M, Isenberg E, Grauer MT, Hamann G, Schimrigk K: CSF substance P somatostatin and monoaminergic transmitter metabolites in patients with narcolepsy. Neurosci Lett. 1996 Nov 1;218(2):99-102. Pubmed: 8945737
  36. Curtin F, Walker JP, Peyrin L, Soulier V, Badan M, Schulz P: Reward dependence is positively related to urinary monoamines in normal men. Biol Psychiatry. 1997 Aug 15;42(4):275-81. Pubmed: 9270904
  37. Abramowsky CR, Taylor SR, Anton AH, Berk AI, Roederer M, Murphy RF: Flow cytometry DNA ploidy analysis and catecholamine secretion profiles in neuroblastoma. Cancer. 1989 May 1;63(9):1752-6. Pubmed: 2702581
  38. Sumiyoshi T, Yotsutsuji T, Kurachi M, Itoh H, Kurokawa K, Saitoh O: Effect of mental stress on plasma homovanillic acid in healthy human subjects. Neuropsychopharmacology. 1998 Jul;19(1):70-3. Pubmed: 9608578
  39. Jolicoeur FB, Rivest R, Drumheller A: Hypokinesia, rigidity, and tremor induced by hypothalamic 6-OHDA lesions in the rat. Brain Res Bull. 1991 Feb;26(2):317-20. Pubmed: 1901508
  40. Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. Pubmed: 115032
  41. di Rocco A, Bottiglieri T, Dorfman D, Werner P, Morrison C, Simpson D: Decreased homovanilic acid in cerebrospinal fluid correlates with impaired neuropsychologic function in HIV-1-infected patients. Clin Neuropharmacol. 2000 Jul-Aug;23(4):190-4. Pubmed: 11020122
  42. Van Der Heyden JC, Rotteveel JJ, Wevers RA: Decreased homovanillic acid concentrations in cerebrospinal fluid in children without a known defect in dopamine metabolism. Eur J Paediatr Neurol. 2003;7(1):31-7. Pubmed: 12615172
  43. Brautigam C, Wevers RA, Jansen RJ, Smeitink JA, de Rijk-van Andel JF, Gabreels FJ, Hoffmann GF: Biochemical hallmarks of tyrosine hydroxylase deficiency. Clin Chem. 1998 Sep;44(9):1897-904. Pubmed: 9732974
  44. Amin F, Stroe AE, Kahn T, Knott PJ, Kahn RS, Davidson M: Control of renal factors in plasma homovanillic acid measurements. Neuropsychopharmacology. 1998 Apr;18(4):317-20. Pubmed: 9509499
  45. Mashige F, Ohkubo A, Matsushima Y, Takano M, Tsuchiya E, Kanazawa H, Nagata Y, Takai N, Shinozuka N, Sakuma I: High-performance liquid chromatographic determination of catecholamine metabolites and 5-hydroxyindoleacetic acid in human urine using a mixed-mode column and an eight-channel electrode electrochemical detector. J Chromatogr B Biomed Appl. 1994 Aug 5;658(1):63-8. Pubmed: 7524950
  46. Lambert GW, Eisenhofer G, Esler MD: The influence of aging on the plasma concentration and renal clearance of homovanillic acid. Psychoneuroendocrinology. 1994;19(1):33-41. Pubmed: 9210210
  47. Konradi C, Kornhuber J, Sofic E, Heckers S, Riederer P, Beckmann H: Variations of monoamines and their metabolites in the human brain putamen. Brain Res. 1992 May 8;579(2):285-90. Pubmed: 1628216
  48. Riddle MA, Jatlow PI, Anderson GM, Cho SC, Hardin MT, Cohen DJ, Leckman JF: Plasma debrisoquin levels in the assessment of reduction of plasma homovanillic acid. The debrisoquin method. Neuropsychopharmacology. 1989 Jun;2(2):123-9. Pubmed: 2742727
  49. Honma T, Miyagawa M, Suda M, Wang RS, Kobayashi K, Sekiguchi S: Effects of perinatal exposure to bisphenol A on brain neurotransmitters in female rat offspring. Ind Health. 2006 Jul;44(3):510-24. Pubmed: 16922197
  50. Sambo P, Baroni SS, Luchetti M, Paroncini P, Dusi S, Orlandini G, Gabrielli A: Oxidative stress in scleroderma: maintenance of scleroderma fibroblast phenotype by the constitutive up-regulation of reactive oxygen species generation through the NADPH oxidase complex pathway. Arthritis Rheum. 2001 Nov;44(11):2653-64. Pubmed: 11710721
  51. Ferreira C, Paes M, Gouveia A, Ferreira E, Padua F, Fiuza T: Plasma homovanillic acid and prolactin in systemic lupus erythematosus. Lupus. 1998;7(6):392-7. Pubmed: 9736322
  52. Post RM, Goodwin FK: Time-dependent effects of phenothiazines on dopamine turnover in psychiatric patients. Science. 1975 Oct 31;190(4213):488-9. Pubmed: 1166321
  53. Azzaro AJ, King J, Kotzuk J, Schoepp DD, Frost J, Schochet S: Guinea pig striatum as a model of human dopamine deamination: the role of monoamine oxidase isozyme ratio, localization, and affinity for substrate in synaptic dopamine metabolism. J Neurochem. 1985 Sep;45(3):949-56. Pubmed: 3928811
  54. Silbergeld EK, Chisolm JJ Jr: Lead poisoning: altered urinary catecholamine metabolites as indicators of intoxication in mice and children. Science. 1976 Apr 9;192(4235):153-5. Pubmed: 1257763
  55. Kish SJ, Shannak K, Rajput A, Deck JH, Hornykiewicz O: Aging produces a specific pattern of striatal dopamine loss: implications for the etiology of idiopathic Parkinson's disease. J Neurochem. 1992 Feb;58(2):642-8. Pubmed: 1729408
  56. Kania BF: Presynaptic stimulation of dopaminergic CNS structures in sheep as a mechanism of immobilising action of Immobyl (fentanyl + azaperone). Res Vet Sci. 1985 Mar;38(2):179-83. Pubmed: 4039834
  57. Ebinger G, Michotte Y, Herregodts P: The significance of homovanillic acid and 3,4-dihydroxyphenylacetic acid concentrations in human lumbar cerebrospinal fluid. J Neurochem. 1987 Jun;48(6):1725-9. Pubmed: 3572399
  58. Burman P, Hetta J, Wide L, Mansson JE, Ekman R, Karlsson FA: Growth hormone treatment affects brain neurotransmitters and thyroxine [see comment] Clin Endocrinol (Oxf). 1996 Mar;44(3):319-24. Pubmed: 8729530
  59. Narayan M, Srinath S, Anderson GM, Meundi DB: Cerebrospinal fluid levels of homovanillic acid and 5-hydroxyindoleacetic acid in autism. Biol Psychiatry. 1993 Apr 15-May 1;33(8-9):630-5. Pubmed: 7687150
  60. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473
  61. Bowers MB Jr, Hoffman FJ Jr, Morton JB: Diazepam and haloperidol. Effect on regional brain homovanillic acid levels. Neuropsychopharmacology. 1991 Aug;5(1):65-9. Pubmed: 1930613
  62. Amin F, Silverman JM, Siever LJ, Smith CJ, Knott PJ, Davis KL: Genetic antecedents of dopamine dysfunction in schizophrenia. Biol Psychiatry. 1999 May 1;45(9):1143-50. Pubmed: 10331106

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxybenzeneacetic acid → S-Adenosylhomocysteine + Homovanillic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Homovanillin + NAD + Water → Homovanillic acid + NADH + Hydrogen Iondetails
Homovanillin + NADP + Water → Homovanillic acid + NADPH + Hydrogen Iondetails