Homovanillic acid
Chemical compound
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Names | ||
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Preferred IUPAC name
(4-Hydroxy-3-methoxyphenyl)acetic acid
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Other names
2-(4-Hydroxy-3-methoxyphenyl)acetic acid; 3-Methoxy-4-hydroxyphenylacetic acid; 4-Hydroxy-3-methoxy-benzeneacetic acid
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Identifiers | ||
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3D model (
JSmol
)
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ChEBI | ||
ChEMBL | ||
ChemSpider |
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ECHA InfoCard |
100.005.616
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KEGG |
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MeSH | Homovanillic+acid | |
PubChem
CID
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UNII | ||
CompTox Dashboard
(
EPA
)
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Properties | ||
C 9 H 10 O 4 | ||
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).
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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
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
catecholamines |
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tryptophan → serotonin |
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serotonin → melatonin |
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