Homovanillic acid

Last updated
Homovanillic acid
Homovanillic acid.svg
Homovanillic acid 3D ball.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Homovanillic+acid
PubChem CID
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) Yes check.svgY
    Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancewhite solid
Melting point 138-140 °C
17 mg/mL
log P 0.33
Vapor pressure 0.00000823 mmHg
Acidity (pKa)pKa1 = 4.41
pKa2 = 10.53
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

References

  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.
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