3-Methoxy-4-hydroxyphenylglycol

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3-Methoxy-4-hydroxyphenylglycol

IUPAC name 1-(4-Hydroxy-3-methoxyphenyl) ethane-1,2-diol
Other names MHPG
Identifiers
CAS number	67423-45-4
PubChem	10805
ChemSpider	10348^Y
KEGG	C05594^Y
MeSH	Methoxyhydroxyphenylglycol
Jmol-3D images	Image 1 Image 2
SMILES COC1=C(C=CC(=C1)C(CO)O)O Oc1ccc(cc1OC)C(O)CO
InChI InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3^Y Key: FBWPWWWZWKPJFL-UHFFFAOYSA-N^Y InChI=1/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3 Key: FBWPWWWZWKPJFL-UHFFFAOYAR
Properties
Molecular formula	C₉H₁₂O₄
Molar mass	184.18918
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG) is a metabolite of norepinephrine degradation. In the brain, it is the principal norepinephrine metabolite. It is released into the blood and cerebrospinal fluid,^[1] and a blood sample of it may therefore be an indication of recent sympathetic nervous system activity.

Low levels of it in the blood and CSF are connected to Anorexia nervosa.

Norepinephrine degradation. 3-Methoxy-4-hydroxyphenylglycol is shown at right. Enzymes are shown in boxes.^[2]

References

^ Increase in cerebrospinal fluid and plasma levels of 3-methoxy-4- hydroxyphenylglycol in acute stroke T Kanda, K Azuma, F Sakai and Y Tazaki. Department of Internal Medicine, School of Medicine, Kitasato University, Sagamihara, Japan.
^ Figure 11-4 in: Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5.

Neurotransmitter metabolic intermediates

catecholamines

Anabolism (tyrosine→epinephrine)	Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine

Catabolism/ metabolites	dopamine: DOPAL · DOPAC · MOPET · Hydroxytyrosol · 3-Methoxytyramine · Homovanillic acid norepinephrine: 3,4-Dihydroxymandelic acid · Normetanephrine · Vanillylmandelic acid · 3-Methoxy-4-hydroxyphenylglycol · Dihydroxyphenylethylene glycol epinephrine: Metanephrine

tryptophan→serotonin

anabolism: 5-Hydroxytryptophan
catabolism: 5-Hydroxyindoleacetic acid

serotonin→melatonin

Normelatonin

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

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