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Homovanillic acid

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Title: Homovanillic acid  
Author: World Heritage Encyclopedia
Language: English
Subject: Vanillylmandelic acid, 3,4-Dihydroxyphenylacetic acid, 3-Methoxytyramine, Dopamine, HVA
Collection: Neurochemistry, O-Methylated Natural Phenols, Phenolic Human Metabolites, Vanilloids
Publisher: World Heritage Encyclopedia

Homovanillic acid

Homovanillic acid
Structural formula of homovanillic acid
Ball-and-stick model of the homovanillic acid molecule
IUPAC name
2-(4-Hydroxy-3-methoxy-phenyl)acetic acid
ChemSpider  Y
Jmol-3D images Image
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).
 Y  (: Y/N?)

Homovanillic acid (HOC6H3(OCH3)CH2COOH; synonyms: 3-methoxy-4-hydroxyphenyl acetic acid; HVA; 4-hydroxy-3-methoxy-benzeneacetic acid; 4-hydroxy-3-methoxyphenylacetic acid) is a major catecholamine metabolite and is produced throughout the body.[1] It 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. 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 transsexuals according to their genetic sex, both before and during cross-sex hormone administration. Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.[3]

See also


  1. ^ Lambert, G.W.; Eisenhofer, G.; Jennings, G.L.; Esler, M.D. "Regional homovanillic acid production in humans". Life Sciences 53 (1): 63–75.  
  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".  
  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 transsexual subjects".  
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