関: 4-hydroxy-3-methoxyphenylglycol、MHPG

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/16 01:13:16」(JST)

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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.

English Journal

Norepinephrine and its metabolites are involved in the synthesis of neuromelanin derived from the locus coeruleus.

Wakamatsu K1, Tabuchi K1, Ojika M2, Zucca FA3, Zecca L3, Ito S1.
Journal of neurochemistry.J Neurochem.2015 Nov;135(4):768-76. doi: 10.1111/jnc.13237. Epub 2015 Sep 4.
In order to elucidate the chemical structure of black to brown pigments, neuromelanins (NMs), in the substantia nigra (SN) and the locus coeruleus (LC) in the central nervous system of humans and other mammalian species during aging, chemical degradative methods are powerful tools. HPLC analysis aft
PMID 26156066

Cerebrospinal fluid monoamine metabolite concentrations as intermediate phenotypes between glutamate-related genes and psychosis.

Andreou D1, Söderman E2, Axelsson T3, Sedvall GC2, Terenius L2, Agartz I4, Jönsson EG5.
Psychiatry research.Psychiatry Res.2015 Sep 30;229(1-2):497-504. doi: 10.1016/j.psychres.2015.06.023. Epub 2015 Jun 27.
Glutamate-related genes have been associated with schizophrenia, but the results have been ambiguous and difficult to replicate. Homovanillic acid (HVA), 5-hydroxyindoleacetic acid (5-HIAA) and 3-methoxy-4-hydroxyphenylglycol (MHPG) are the major degradation products of the monoamines dopamine, sero
PMID 26142836

Peripheral Neuropathy Induces HCN Channel Dysfunction in Pyramidal Neurons of the Medial Prefrontal Cortex.

Cordeiro Matos S1, Zhang Z1, Séguéla P2.
The Journal of neuroscience : the official journal of the Society for Neuroscience.J Neurosci.2015 Sep 23;35(38):13244-56. doi: 10.1523/JNEUROSCI.0799-15.2015.
Neuropathic pain is a debilitating condition for which the development of effective treatments has been limited by an incomplete understanding of its molecular basis. The cationic current Ih mediated by hyperpolarization-activated cyclic nucleotide-gated (HCN) channels plays an important role in pai
PMID 26400952

Japanese Journal

Brain glycogen decreases during prolonged exercise

Matsui Takashi,Soya Shingo,Okamoto Masahiro,Ichitani Yukio,Kawanaka Kentaro,Soya Hideaki,松井崇,征矢英昭
The Journal of physiology 589(13), 3383-3393, 2011-06
… Further, in the cortex, the levels of methoxyhydroxyphenylglycol (MHPG) and 5-hydroxyindoleacetic acid (5-HIAA) with potential involvement in degradation of the brain glycogen increased during prolonged exercise and negatively correlated with the glycogen levels. …
NAID 120004288251

Related Pictures

Norepinephrine degradation. Catechol-O Neurochemistry II flashcards | Quizlet Peripheral blood mononuclear cells Lourdes Leon HairstylesAll New Hairstyles Dopamine degradation. Voltage-clamp analysis of voltage-gated Hydroxy-3-methoxyphenyl) ethane-1,2 Metoxi-4-hidroxifenilglicol

★リンクテーブル★

リンク元	「カテコールアミン」「MHPG」「メトキシヒドロキシフェニルグリコール」「4-hydroxy-3-methoxyphenylglycol」

「カテコールアミン」

3-Methoxy-4-hydroxyphenylglycol
Names
	IUPAC name 1-(4-Hydroxy-3-methoxyphenyl) ethane-1,2-diol
	Other names MHPG
Identifiers
CAS Registry Number	67423-45-4
ChemSpider	10348
	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 ; Key: FBWPWWWZWKPJFL-UHFFFAOYSA-N ; 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 ;
Jmol-3D images	Image; Image
KEGG	C05594
MeSH	Methoxyhydroxyphenylglycol
PubChem	10805
	SMILES 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

　　[★]

英: catecholamine catecholamines CA
同: カテコラミン
関: 副腎髄質ホルモン

カテコールでかつアミンを持つ構造

Wikipedia

ドーパミン、ノルアドレナリン、アドレナリン

生合成

チロシン tyrosine
 (フェニル基の3位にOHを導入) ：律速酵素
 -チロシン 3-モノオキシゲナーゼ tyrosine 3-monooxygenase, チロシン水酸化酵素 tyrosine hydroxylase
 ←{H₄・biopterin}
 →{H₂・biopterin}
L-ドーパ L-dopa
 (アミノ酸から脱炭酸)
 -芳香族アミノ酸デカルボキシラーゼ dopa decarboxylase + {ピリドキサル5-リン酸(VB₆)}
 →CO₂
ドパミン dopamine
 (β位の炭素にOHを導入)
 -ドーパミン β-モノオキシゲナーゼ dopamine β-monoxygenase, dopamine β-odidase
 ←O₂ + ビタミンC(アスコルビン酸)
 →H₂O + デヒドロアスコルビン酸
ノルアドレナリン norepinephrine
 (アミノ基にメチル基を転移)
 -フェニルエタノールアミン N-メチルトランスフェラーゼ phenylethanolamine N-methyl transferase
 ←S-アデノシルメチオニン S-adenosylmethionine
 →S-アデノシルホモシステイン S-adenosylhemocysteine
アドレナリン epinephrine

分解

ドパミン、ノルアドレナリン、アドレナリンはいずれも以下の酵素により分解される

分解産物

ドパミン dopamine	－－－→	ジヒドロキシフェニル酢酸 3,4-dihydroxyphenylacetic acid DOPAC	－－－→	ホモバニリン酸 homovanillic acid HVA
｜｜	MAO COMT
｜｜ ↓
ノルエピネフリン norepinephrine	－－－→	バニリルマンデリン酸 vanillylmandelic acid VMA 　　　　　　　・メトキシヒドロキシフェニルグリコール methoxyhydroxyphenylglycol MHPG
｜｜ ↓	MAO COMT
エピネフリン epinephrine	－－－→
	MAO COMT