3-Methoxy-4-hydroxyphenylglycol

3-Methoxy-4-hydroxyphenylglycol
Names
IUPAC name
1-(4-Hydroxy-3-methoxyphenyl) ethane-1,2-diol
Other names
MHPG
Identifiers
CAS Number
  • 534-82-7 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 10348 checkY
KEGG
  • C05594 checkY
MeSH Methoxyhydroxyphenylglycol
PubChem CID
  • 10805
UNII
  • 98LK01183Z checkY
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 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
Chemical formula
 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
Chemical compound

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 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.