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
KEGG
MeSH Homovanillic+acid
Properties
C9H10O4
Molar mass 182.18 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. "Regional homovanillic acid production in humans". Life Sciences. 53 (1): 63–75. doi:10.1016/0024-3205(93)90612-7. 
  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. PMID 16214946.