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;
UNII	X77S6GMS36 ;
CompTox Dashboard (EPA)	DTXSID5059791 ;
	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	182.175 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.^{[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.

^ 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.

[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.

[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. hdl:2066/47682. PMID 16214946. Archived from the original on 2011-02-27. Retrieved 2011-01-30.

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