ContaminantDB: Homovanillic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:29:15 UTC

Update Date

2026-05-21 14:38:36 UTC

Accession Number

CHEM003297

Identification

Common Name

Homovanillic acid

Class

Small Molecule

Description

Homovanillic 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.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Ether
Food Toxin
Indicator and Reagent
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4-Hydroxy-3-methoxyphenyl)acetic acid	ChEBI
3-Methoxy-4-hydroxyphenylacetate	ChEBI
3-Methoxy-4-hydroxyphenylacetic acid	ChEBI
4-Hydroxy-3-methoxybenzeneacetic acid	ChEBI
HVA	ChEBI
Vanillacetic acid	ChEBI
(4-Hydroxy-3-methoxyphenyl)acetate	Generator
4-Hydroxy-3-methoxybenzeneacetate	Generator
Vanillacetate	Generator
Homovanillate	Generator
3-Methoxy-4-hydroxy-phenylacetic acid	HMDB
4-Hydroxy 3-methoxyphenylacetic acid	HMDB
4-Hydroxy-3-methoxyphenylacetic acid	HMDB
Homovanilate	HMDB
Homovanilic acid	HMDB
Homovanillinic acid	HMDB
Vanilacetate	HMDB
Vanilacetic acid	HMDB
3 Methoxy 4 hydroxyphenylacetic acid	HMDB
Acid, 3-methoxy-4-hydroxyphenylacetic	HMDB
Acid, 4-hydroxy-3-methoxyphenylacetic	HMDB
4 Hydroxy 3 methoxyphenylacetic acid	HMDB
Acid, homovanillic	HMDB
3'-Methoxy-4'-hydroxyphenylacetic acid	HMDB
3’-methoxy-4’-hydroxyphenylacetic acid	HMDB
4'-Hydroxy-3'-methoxy-phenylacetic acid	HMDB
2-(4-Hydroxy-3-methoxyphenyl)acetic acid	HMDB
4'-Hydroxy-3'-methoxyphenylacetic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Mass

182.173 g/mol

Monoisotopic Mass

182.058 g/mol

CAS Registry Number

306-08-1

IUPAC Name

Not Available

Traditional Name

homovanillic acid

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 Key

QRMZSPFSDQBLIX-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Organic compounds

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:545959 )
phenols (CHEBI:545959 )
monomethoxybenzene (CHEBI:545959 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Brain
Caudate Nucleus
Central Nervous System
Fibroblasts
Kidney
Spinal Cord
Striatum

Pathways

Name	SMPDB Link	KEGG Link
Tyrosine Metabolism	SMP00006	map00350
Dopamine beta-hydroxylase deficiency	SMP00498	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	138 - 140°C
Boiling Point	Not Available
Solubility	17 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	2.72 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.15	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.81 m³·mol⁻¹	ChemAxon
Polarizability	17.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-056r-1962000000-4f8e427392aa8e136095	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-056r-2972000000-f53a7b3ac40c099e3c99	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9800000000-def178a40b9d8cc16724	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06vi-0596000000-729a4b24107b98261cb2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056r-1962000000-4f8e427392aa8e136095	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-056r-2972000000-f53a7b3ac40c099e3c99	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056r-1962000000-24557ef3db49c59cd5dd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-cb0e3eb7a6d9e785a2f8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01w0-9352000000-0e2f11bc503dd5ce6345	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-994a78c607c1b6a724d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00fr-4900000000-ca5ef14a72dcdf3cf9fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00dl-9700000000-44f2784ec5407e93ea57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0019-0900000000-aafe8aee1cf8c42b941a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-1900000000-313fe6eb451badd5c052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0609-6900000000-11aa4fb169e782205ea3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-9200000000-637a59b417fe2b2e7f58	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-9000000000-7b87b58730add4511c8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0019-0900000000-aafe8aee1cf8c42b941a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-1900000000-313fe6eb451badd5c052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0609-6900000000-11aa4fb169e782205ea3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9200000000-1bc951858c2e658a79af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-7b87b58730add4511c8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0900000000-0c3c4c703b4b9743a521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0900000000-a5e048e5e58ed8e57ecd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0079-0900000000-35fbf40336719c96dd3d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-b408942abbf2cafac06e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-39dd2b8775ad5c5ec2f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4900000000-c9fd7643f48c0e43dc87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-57e5685e37a2d70f9ab4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0900000000-b8470b9851db4df96b61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-3900000000-2690d7c586d4f7c3dccf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-0900000000-713f0600845faa67fec3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-0900000000-30a79a8a4d5cf0ffc864	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-2900000000-6f967f9e7f7117a9d1e4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-3900000000-b8c848b70c066282b36f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Homovanillic_acid

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

MSDS

General References

1. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. Reynolds GP, Garrett NJ: Striatal dopamine and homovanillic acid in Huntington's disease. J Neural Transm. 1986;65(2):151-5.

8. 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.

9. 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.

10. 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.

11. 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.

12. 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.

13. Lambert GW, Eisenhofer G, Jennings GL, Esler MD: Regional homovanillic acid production in humans. Life Sci. 1993;53(1):63-75.

14. 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.

15. 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.

16. 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.

17. 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.

18. 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.

19. 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.

20. 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.

21. 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.

22. 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.

23. 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.

24. 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.

25. 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.

26. 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.

27. Lembreghts M, Ansseau M: [Biological markers in schizophrenia]. Encephale. 1993 Sep-Oct;19(5):501-23.

28. 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.

29. 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.

30. 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.

31. 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.

32. 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.

33. 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.

34. 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.

35. 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.

36. 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.

37. 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.

38. 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.

39. 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.

40. 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.

41. 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.

42. 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.

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.

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.

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.

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.

47. 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.

48. 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.

49. 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.

50. 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.

51. 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.

52. 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.

53. Post RM, Goodwin FK: Time-dependent effects of phenothiazines on dopamine turnover in psychiatric patients. Science. 1975 Oct 31;190(4213):488-9.

54. 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.

55. 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.

56. 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.

57. 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.

58. 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.

59. 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.

60. 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.

61. 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.

62. 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.

63. 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.

64. Boto-Ordonez M, Urpi-Sarda M, Queipo-Ortuno MI, Tulipani S, Tinahones FJ, Andres-Lacueva C: High levels of Bifidobacteria are associated with increased levels of anthocyanin microbial metabolites: a randomized clinical trial. Food Funct. 2014 Aug;5(8):1932-8. doi: 10.1039/c4fo00029c.

65. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510

66. https://www.ncbi.nlm.nih.gov/pubmed/?term=10331106

67. https://www.ncbi.nlm.nih.gov/pubmed/?term=11020122

68. https://www.ncbi.nlm.nih.gov/pubmed/?term=115032

69. https://www.ncbi.nlm.nih.gov/pubmed/?term=1166321

70. https://www.ncbi.nlm.nih.gov/pubmed/?term=11710721

71. https://www.ncbi.nlm.nih.gov/pubmed/?term=1257763

72. https://www.ncbi.nlm.nih.gov/pubmed/?term=12615172

73. https://www.ncbi.nlm.nih.gov/pubmed/?term=12649306

74. https://www.ncbi.nlm.nih.gov/pubmed/?term=12891653

75. https://www.ncbi.nlm.nih.gov/pubmed/?term=14688447

76. https://www.ncbi.nlm.nih.gov/pubmed/?term=1537368

77. https://www.ncbi.nlm.nih.gov/pubmed/?term=15652629

78. https://www.ncbi.nlm.nih.gov/pubmed/?term=15843212

79. https://www.ncbi.nlm.nih.gov/pubmed/?term=16259647

80. https://www.ncbi.nlm.nih.gov/pubmed/?term=1628216

81. https://www.ncbi.nlm.nih.gov/pubmed/?term=16288991

82. https://www.ncbi.nlm.nih.gov/pubmed/?term=16922197

83. https://www.ncbi.nlm.nih.gov/pubmed/?term=1712114

84. https://www.ncbi.nlm.nih.gov/pubmed/?term=1729408

85. https://www.ncbi.nlm.nih.gov/pubmed/?term=1901508

86. https://www.ncbi.nlm.nih.gov/pubmed/?term=1930613

87. https://www.ncbi.nlm.nih.gov/pubmed/?term=2026685

88. https://www.ncbi.nlm.nih.gov/pubmed/?term=2193315

89. https://www.ncbi.nlm.nih.gov/pubmed/?term=24007816

90. https://www.ncbi.nlm.nih.gov/pubmed/?term=24010549

91. https://www.ncbi.nlm.nih.gov/pubmed/?term=2409733

92. https://www.ncbi.nlm.nih.gov/pubmed/?term=2416192

93. https://www.ncbi.nlm.nih.gov/pubmed/?term=2428259

94. https://www.ncbi.nlm.nih.gov/pubmed/?term=2428421

95. https://www.ncbi.nlm.nih.gov/pubmed/?term=2437853

96. https://www.ncbi.nlm.nih.gov/pubmed/?term=24416192

97. https://www.ncbi.nlm.nih.gov/pubmed/?term=24423636

98. https://www.ncbi.nlm.nih.gov/pubmed/?term=2480613

99. https://www.ncbi.nlm.nih.gov/pubmed/?term=2581293

100. https://www.ncbi.nlm.nih.gov/pubmed/?term=2604799

101. https://www.ncbi.nlm.nih.gov/pubmed/?term=2644889

102. https://www.ncbi.nlm.nih.gov/pubmed/?term=2702581

103. https://www.ncbi.nlm.nih.gov/pubmed/?term=2742727

104. https://www.ncbi.nlm.nih.gov/pubmed/?term=2939198

105. https://www.ncbi.nlm.nih.gov/pubmed/?term=2991966

106. https://www.ncbi.nlm.nih.gov/pubmed/?term=3000280

107. https://www.ncbi.nlm.nih.gov/pubmed/?term=3263594

108. https://www.ncbi.nlm.nih.gov/pubmed/?term=3400977

109. https://www.ncbi.nlm.nih.gov/pubmed/?term=3572399

110. https://www.ncbi.nlm.nih.gov/pubmed/?term=3797547

111. https://www.ncbi.nlm.nih.gov/pubmed/?term=3928811

112. https://www.ncbi.nlm.nih.gov/pubmed/?term=4039834

113. https://www.ncbi.nlm.nih.gov/pubmed/?term=432666

114. https://www.ncbi.nlm.nih.gov/pubmed/?term=6085084

115. https://www.ncbi.nlm.nih.gov/pubmed/?term=6198473

116. https://www.ncbi.nlm.nih.gov/pubmed/?term=7524950

117. https://www.ncbi.nlm.nih.gov/pubmed/?term=7687150

118. https://www.ncbi.nlm.nih.gov/pubmed/?term=8087979

119. https://www.ncbi.nlm.nih.gov/pubmed/?term=8306920

120. https://www.ncbi.nlm.nih.gov/pubmed/?term=8353435

121. https://www.ncbi.nlm.nih.gov/pubmed/?term=8515683

122. https://www.ncbi.nlm.nih.gov/pubmed/?term=8516085

123. https://www.ncbi.nlm.nih.gov/pubmed/?term=8561958

124. https://www.ncbi.nlm.nih.gov/pubmed/?term=8724671

125. https://www.ncbi.nlm.nih.gov/pubmed/?term=8729530

126. https://www.ncbi.nlm.nih.gov/pubmed/?term=8884658

127. https://www.ncbi.nlm.nih.gov/pubmed/?term=8945737

128. https://www.ncbi.nlm.nih.gov/pubmed/?term=9210210

129. https://www.ncbi.nlm.nih.gov/pubmed/?term=9270904

130. https://www.ncbi.nlm.nih.gov/pubmed/?term=9439441

131. https://www.ncbi.nlm.nih.gov/pubmed/?term=9509499

132. https://www.ncbi.nlm.nih.gov/pubmed/?term=9608578

133. https://www.ncbi.nlm.nih.gov/pubmed/?term=9722142

134. https://www.ncbi.nlm.nih.gov/pubmed/?term=9732974

135. https://www.ncbi.nlm.nih.gov/pubmed/?term=9736322

136. https://www.ncbi.nlm.nih.gov/pubmed/?term=9849813