Homovanillic acid

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Homovanillic acid
Structural formula of homovanillic acid
Ball-and-stick model of the homovanillic acid molecule
Names
Preferred IUPAC name
(4-Hydroxy-3-methoxyphenyl)acetic acid
Other names
2-(4-Hydroxy-3-methoxyphenyl)acetic acid; 3-Methoxy-4-hydroxyphenylacetic acid; 4-Hydroxy-3-methoxy-benzeneacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.616 Edit this at Wikidata
KEGG
MeSH Homovanillic+acid
UNII
  • 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) checkY
    Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N checkY
  • InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
    Key: QRMZSPFSDQBLIX-UHFFFAOYAZ
  • O=C(O)Cc1cc(OC)c(O)cc1
Properties
C9H10O4
Molar mass 182.175 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Homovanillic acid (HVA) is a major catecholamine metabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine.[1] Homovanillic acid is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.

In psychiatry and neuroscience, brain and cerebrospinal fluid levels of HVA are measured as a marker of metabolic stress caused by 2-deoxy-D-glucose.[2] HVA presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.

Fasting plasma levels of HVA are known to be higher in females than in males.[citation needed] This does not seem to be influenced by adult hormonal changes, as the pattern is retained in the elderly and post-menopausal as well as transgender people according to their genetic sex, both before and during cross-sex hormone administration.[3] Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.

See also[edit]

References[edit]

  1. ^ Lambert, G.W.; Eisenhofer, G.; Jennings, G.L.; Esler, M.D. (1993). "Regional homovanillic acid production in humans". Life Sciences. 53 (1): 63–75. doi:10.1016/0024-3205(93)90612-7. PMID 8515683.
  2. ^ Marcelis M, Suckling J, Hofman P, Woodruff P, Bullmore E, van Os J (September 2006). "Evidence that brain tissue volumes are associated with HVA reactivity to metabolic stress in schizophrenia". Schizophr. Res. 86 (1–3): 45–53. doi:10.1016/j.schres.2006.05.001. PMID 16806836.
  3. ^ Giltay E, Kho K, Blandjaar B, Verbeek M, Geurtz P, Geleijnse J, Gooren L (July 2005). "The sex difference of plasma homovanillic acid is unaffected by cross-sex hormone administration in transgender people". J Endocrinol. 187 (1): 109–16. doi:10.1677/joe.1.06307. hdl:2066/47682. PMID 16214946. Archived from the original on 2011-02-27. Retrieved 2011-01-30.
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