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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.^[1]

This product has been synthesized (52% yield) from 4-Hydroxyphenylacetic acid via aerobic biotransformation using whole cell cultures of Arthrobacter protophormiae.^[2]^[3]

References

^ Santos, Sónia A. O.; Freire, Carmen S. R.; Domingues, M. Rosário M.; Silvestre, Armando J. D.; Neto, Carlos Pascoal (2011). "Characterization of Phenolic Components in Polar Extracts of Eucalyptus globulus Labill. Bark by High-Performance Liquid Chromatography–Mass Spectrometry". Journal of Agricultural and Food Chemistry 59 (17): 9386–93. doi:10.1021/jf201801q. PMID 21761864.
^ Robins, Karen T.; Osorio-Lozada, Antonio; Avi, Manuela; Meyer, Hans-Peter (2009). "Lonza: Biotechnology – A Key Ingredient for Success in the Future". CHIMIA International Journal for Chemistry 63 (6): 327–330. doi:10.2533/chimia.2009.327. |accessdate= requires |url= (help)
^ Sutton, Peter; Whittall, John; (2012). Practical Methods for Biocatalysis and Biotransformations 2. Chichester, West Sussex: John Wiley & Sons, Ltd. pp. 150–153. ISBN 9781119991397.

English Journal

Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae), decreases serotonin levels in rat hippocampus.

Farias FM, Passos CS, Arbo MD, Barros DM, Gottfried C, Steffen VM, Henriques AT.SourceCurso de Farmácia, Universidade Federal do Pampa, BR 472 km 592, CEP 97500-970, Uruguaiana, RS, Brazil.
Fitoterapia.Fitoterapia.2012 Sep;83(6):1138-43. Epub 2012 Apr 21.
Psychotria is a complex genus whose neotropical species are known by the presence of glucosidic monoterpene indole alkaloids. These compounds are able to display a large range of effects on the central nervous system, such as anxiolytic, antidepressant, analgesic, and impairment of learning and memo
PMID 22546150

Neuroprotection by Silencing iNOS Expression in a 6-OHDA Model of Parkinson's Disease.

Li M, Dai FR, Du XP, Yang QD, Chen Y.SourceDepartment of Neurology, Xiangya Hospital, Central South University, Changsha, 410008, People's Republic of China.
Journal of molecular neuroscience : MN.J Mol Neurosci.2012 Sep;48(1):225-33. Epub 2012 May 26.
In this study, we investigated the protective role of silenced iNOS expression in neuron death in the nigrostriatal pathway in a 6-OHDA animal model of Parkinson's disease (PD). The animal model was established by intrastriatal infusion of a single dose of 6-OHDA. Silencing of iNOS expression was es
PMID 22638860

Japanese Journal

Nasal instillation of nanoparticle-rich diesel exhaust particles slightly affects emotional behavior and learning capability in rats

YOKOTA Syunji,TAKASHIMA Hiromasa,OHTA Ryo,SAITO Yoshiaki,MIYAHARA Takashi,YOSHIDA Yuka,NEGURA Tsukasa,SENUMA Mika,USUMI Kenji,HIRABAYASHI Naoyuki,WATANABE Takaho,HORIUCHI Shinji,FUJITANI Yuji,HIRANO Seishiro,FUJIMAKI Hidekazu
Journal of toxicological sciences 36(3), 267-276, 2011-06-01
… The levels of dopamine and its metabolite (DOPAC) in the medial mammillary nucleus of the brain tended to be lower in the NRDEP-treated animals. …
NAID 10029135704

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

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★リンクテーブル★

リンク元	「カテコールアミン」「3,4-dihydroxyphenylacetic acid」「ジヒドロキシフェニル酢酸」
関連記事	「DOPA」

「カテコールアミン」

3,4-Dihydroxyphenylacetic acid
	IUPAC name 2-(3,4-Dihydroxyphenyl)acetic acid
Identifiers
CAS number	102-32-9
PubChem	547
ChemSpider	532
DrugBank	DB01702
MeSH	3,4-Dihydroxyphenylacetic+Acid
ChEBI	CHEBI:41941
ChEMBL	CHEMBL1284
Jmol-3D images	Image 1
	SMILES O=C(O)Cc1cc(O)c(O)cc1 ;
	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) ; Key: CFFZDZCDUFSOFZ-UHFFFAOYSA-N 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 ;
Properties
Molecular formula	C8H8O4
Molar mass	168.15 g mol−1
	Except where noted otherwise, 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