Homovanillic acid

Homovanillic acid
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
CAS Number	306-08-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:545959 ;
ChEMBL	ChEMBL1562 ;
ChemSpider	1675 ;
ECHA InfoCard	100.005.616
KEGG	C05582 ;
MeSH	Homovanillic+acid
PubChem CID	1738;
	InChI 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) Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N ; 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;
	SMILES O=C(O)Cc1cc(OC)c(O)cc1;
Properties
Chemical formula	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).
	verify (what is ?)
	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. 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.

References

↑ 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.
↑ 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. PMID 16214946.

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[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.

[pmid16806836-2] 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.

Homovanillic acid

See also

References