3-Methoxy-4-hydroxyphenylglycol

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.

3-Methoxy-4-hydroxyphenylglycol
Names
IUPAC name
1-(4-Hydroxy-3-methoxyphenyl) ethane-1,2-diol
Other names
MHPG
Identifiers
3D model (JSmol)
ChemSpider
KEGG
MeSH Methoxyhydroxyphenylglycol
UNII
  • InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3 checkY
    Key: FBWPWWWZWKPJFL-UHFFFAOYSA-N checkY
  • 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
  • COC1=C(C=CC(=C1)C(CO)O)O
  • Oc1ccc(cc1OC)C(O)CO
Properties
C9H12O4
Molar mass 184.18918
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Low levels of MHPG in the blood and cerebrospinal fluid are associated with anorexia nervosa and pathological gambling, indicating that norepinephrine may play a role in these behaviors.[2]

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

References
  1. 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.
  2. "Pharmacologic Approaches to the Treatment of Pathological Gambling". Mental Health eJournal. 1998;3(3). Medscape.
  3. Figure 11-4 in: Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 978-0-443-06911-6.
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