3,4-dihydroxyphenylacetic acid

• ドパミン中間代謝産物
• 3,4-ジヒドロキシフェニル酢酸、ジヒドロキシフェニル酢酸

関

DOPAC

WordNet

1. street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
2. any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
3. having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

1. 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/20 17:27:36」(JST)

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3,4-Dihydroxyphenylacetic acid

Names
Preferred IUPAC name (3,4-Dihydroxyphenyl)acetic acid
Other names 2-(3,4-Dihydroxyphenyl)acetic acid
Identifiers
CAS Number	102-32-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:41941 Y
ChEMBL	ChEMBL1284 Y
ChemSpider	532 Y
DrugBank	DB01702 Y
ECHA InfoCard	100.002.750
MeSH	3,4-Dihydroxyphenylacetic+Acid
PubChem	547
UNII	KEX5N0R4N5 N
InChI InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) Y Key: CFFZDZCDUFSOFZ-UHFFFAOYSA-N Y InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) Key: CFFZDZCDUFSOFZ-UHFFFAOYAU
SMILES O=C(O)Cc1cc(O)c(O)cc1
Properties
Chemical formula	C8H8O4
Molar mass	168.15 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine.

Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline).

DOPAC can be oxidized by hydrogen peroxide, leading to the formation of toxic metabolites which destroy dopamine storage vesicles in the substantia nigra. This may contribute to the failure of levodopa treatment of Parkinson's disease. A MAO-B inhibitor such as selegiline or rasagiline can prevent this from happening.

Biodegradation of dopamine

It can also be found in the bark of Eucalyptus globulus.

This product has been synthesized (52% yield) from 4-Hydroxyphenylacetic acid via aerobic biotransformation using whole cell cultures of Arthrobacter protophormiae.

References

UpToDate Contents

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• 1. 尿酸腎結石症 uric acid nephrolithiasis
• 2. 胃酸分泌の生理学 physiology of gastric acid secretion
• 3. 尿酸による腎疾患 uric acid renal diseases
• 4. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
• 5. バルプロ酸中毒 valproic acid poisoning

English Journal

• Effects of acute exposure to exogenous ammonia on cerebral monoaminergic neurotransmitters in juvenile Solea senegalensis.

• Weber RA, Maceira JJ, Mancebo MJ, Peleteiro JB, Martín LO, Aldegunde M.SourceDepartamento de Fisiología, Laboratorio de Fisiología Animal, Facultad de Biología, Campus Vida s/n, Universidad de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
• Ecotoxicology (London, England).Ecotoxicology.2012 Mar;21(2):362-9. Epub 2011 Oct 5.
• The present study explored the potential role of brain catecholaminergic and serotoninergic systems as neuronal targets for the toxicological effects of acute ammonia exposure (0.28 mg l(-1) of un-ionized ammonia for 12 and 24 h) in juvenile sole (Solea senegalensis). In addition, plasma cortisol
• PMID 21971970

• In vitro fermentation of a red wine extract by human gut microbiota: changes in microbial groups and formation of phenolic metabolites.

• Sanchez-Patan F, Cueva C, Monagas M, Walton GE, Gibson GR, Lebrón-Aguilar R, Quintanilla JE, Martin-Alvarez PJ, Moreno-Arribas MV, Bartolome B.AbstractAn in vitro batch culture fermentation experiment was conducted with faecal inocula from three healthy volunteers in the presence and absence of a red wine extract. Changes in main bacterial groups were determined by FISH during a 48 h fermentation period. The catabolism of main flavonoids (i.e., flavan-3-ols and anthocyanins) and the formation of wide a range of phenolic microbial metabolites were determined by a targeted UPLC-PAD-ESI-TQ MS method. Statistical analysis revealed that catechol/pyrocatechol, as well as 4-hydroxy-5-(phenyl)-valeric, 3- and 4-hydroxyphenylacetic, phenylacetic, phenylpropionic, and benzoic acids showed the greatest increases observed during fermentation, whereas 5-(3'-hydroxyphenyl)--valerolactone, its open form 4-hydroxy-5-(3'-hydroxyphenyl)-valeric acid and 3,4-dihydroxyphenylacetic acid represented the largest inter-individual variations in the catabolism of red wine polyphenols. Despite these changes, microbial metabolism did not produce significant changes in the main bacterial groups detected although a slight inhibition of the Clostridium histolyticum group was observed.
• Journal of agricultural and food chemistry.J Agric Food Chem.2012 Feb 7. [Epub ahead of print]
• An in vitro batch culture fermentation experiment was conducted with faecal inocula from three healthy volunteers in the presence and absence of a red wine extract. Changes in main bacterial groups were determined by FISH during a 48 h fermentation period. The catabolism of main flavonoids (i.e., fl
• PMID 22313337

• Coupled intracerebral microdialysis and electrophysiology for the assessment of dopamine neuron function in vivo.

• Panin F, Cathala A, Piazza PV, Spampinato U.SourceInserm U862, Neurocentre Magendie, Physiopathology of Addiction Group, 146 rue Léo Saignât, 33076, Bordeaux F-33000, France; Université de Bordeaux, 146 rue Léo Saignât, 33076, Bordeaux F-33000, France.
• Journal of pharmacological and toxicological methods.J Pharmacol Toxicol Methods.2012 Feb 2. [Epub ahead of print]
• Introduction: The central dopaminergic system is involved in the pathophysiology of several neuropsychiatric disorders. Intracerebral microdialysis and electrophysiology provide two powerful techniques to investigate dopamine (DA) function and the mechanism of action of psychotropic drugs in vivo. M
• PMID 22326873

Japanese Journal

• 3,4-ジヒドロキシフェニル酢酸(DOPAC) (広範囲 血液・尿化学検査 免疫学的検査(第7版・4)その数値をどう読むか) -- (内分泌学的検査 副腎髄質・交感神経系)

• 谷田部 緑,眞田 寛啓
• 日本臨床 68(-) (982), 412-415, 2010-07
• NAID 40017200774

• The Effects of in Utero Exposure to a Migrant, 4,4'-Butylidenebis(6-t-butyl-m-cresol), from Nitrile-Butadiene Rubber Gloves on Monoamine Neurotransmitter in Rats(Biochemistry)

• SATOH Kanako,NONAKA Ryouichi,OHASHI Norio,SHIMIZU Midori,OSHIO Shigeru,TAKEDA Ken
• Biological & pharmaceutical bulletin 31(12), 2211-2215, 2008-12-01
• … 4,4'-Butylidenebis(6-t-butyl-m-cresol) (BBBC) can be eluted from disposable gloves made of nitrile-butadiene rubber and possibly also detected in food. …
• NAID 110007005017

• ENVIRONMENTAL ENRICHMENT MODULATES BEHAVIOR AND MESOCORTICOLIMBIC DOPAMINE SYSTEM IN YOUNG ADULT RAT

• 浦川 将,増田 匡,金 泰善,三角 吉代,飛田 秀樹,西野 仁雄
• Nagoya medical journal 48(2), 139-151, 2007-02-28
• … Furthermore, microdialysis in the NAC indicated that enriched rats showed a lower level in 3, 4-dihydroxyphenylacetic acid and homovanillic acid, major metabolites of DA. …
• NAID 110006426514

Related Links

• 3,4-Dihydroxyphenylacetic acid 98% | Sigma-Aldrich

Sigma-Aldrich offers Aldrich-850217, 3,4-Dihydroxyphenylacetic acid for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Packaging 1, 5 g in glass bottle Application 3,4 ...

• 3,4-Dihydroxyphenylacetic Acid 102-32-9 | 東京化成工業株式会社

[3,4-Dihydroxyphenylacetic Acid] [102-32-9] | 価格や在庫、物性値などの詳細情報ページです。 ... 別名 (英名) 4-Carboxymethylcatechol 別名 (英名) 4-Carboxymethylpyrocatechol 別名 (英名) Catechol-4-acetic Acid 別名 (英名)

Related Pictures

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★リンクテーブル★

リンク元	「カテコールアミン」「ジヒドロキシフェニル酢酸」「3,4-ジヒドロキシフェニル酢酸」「DOPAC」

「カテコールアミン」

　　[★]

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

• MAO monoamine oxidase
• COMT cathechol O-methyltransferase

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

薬理作用

昇圧作用

• (ドパミン、ドブタミン)アシドーシス存在下で効力低下

臨床検査

• 褐色細胞腫、神経芽腫の診断に用いられる。

基準値

カテコールアミン３分画(血漿)(BML)

• アドレナリン：≦0.10 ng/mL
• ノルアドレナリン：0.10～0.50 ng/mL
• ドパミン：≦0.03 ng/mL

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「ジヒドロキシフェニル酢酸」

　　[★]

英

3,4-dihydroxyphenylacetic acid、DOPAC

関

3,4-ジヒドロキシフェニル酢酸

「3,4-ジヒドロキシフェニル酢酸」

　　[★]

英

3,4-dihydroxyphenylacetic acid

関

ジヒドロキシフェニル酢酸

「DOPAC」

　　[★]

ヒドロキシフェニル酢酸

関

3,4-dihydroxyphenylacetic acid