ホモバニリン酸 HVA
WordNet
- 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
- 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
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 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)』「2014/08/28 16:52:01」(JST)
[Wiki en表示]
Homovanillic acid |
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IUPAC name
2-(4-Hydroxy-3-methoxy-phenyl)acetic acid
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Identifiers |
CAS number |
306-08-1 Y |
PubChem |
1738 |
ChemSpider |
1675 Y |
KEGG |
C05582 Y |
MeSH |
Homovanillic+acid |
ChEBI |
CHEBI:545959 Y |
ChEMBL |
CHEMBL1562 Y |
Jmol-3D images |
Image 1 |
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InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12) Y
Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N Y
InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
Key: QRMZSPFSDQBLIX-UHFFFAOYAZ
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Properties |
Molecular formula |
C9H10O4 |
Molar mass |
182.17 g mol−1 |
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
Y (verify) (what is: Y/N?) |
Infobox references |
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Homovanillic acid (HOC6H3(OCH3)CH2COOH; synonyms: 3-methoxy-4-hydroxyphenyl acetic acid; HVA; 4-hydroxy-3-methoxy-benzeneacetic acid; 4-hydroxy-3-methoxyphenylacetic acid) is a major catecholamine metabolite and is produced through out the body.[1] It is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.
In psychiatry and neuroscience, brain and cerebrospinal fluid levels of HVA are measured as a marker of metabolic stress caused by 2-deoxy-D-glucose.[2] HVA presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.
Fasting plasma levels of HVA are known to be higher in females than in males. This does not seem to be influenced by adult hormonal changes, as the pattern is retained in the elderly and post-menopausal as well as transsexuals according to their genetic sex, both before and during cross-sex hormone administration. Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.[3]
See also
References
- ^ Lambert, G.W.; Eisenhofer, G.; Jennings, G.L.; Esler, M.D. "Regional homovanillic acid production in humans". Life Sciences 53 (1): 63–75. doi:10.1016/0024-3205(93)90612-7.
- ^ Marcelis M, Suckling J, Hofman P, Woodruff P, Bullmore E, van Os J (September 2006). "Evidence that brain tissue volumes are associated with HVA reactivity to metabolic stress in schizophrenia". Schizophr. Res. 86 (1–3): 45–53. doi:10.1016/j.schres.2006.05.001. PMID 16806836.
- ^ Giltay E, Kho K, Blandjaar B, Verbeek M, Geurtz P, Geleijnse J, Gooren L (July 2005). "The sex difference of plasma homovanillic acid is unaffected by cross-sex hormone administration in transsexual subjects". J Endocrinol 187 (1): 109–16. doi:10.1677/joe.1.06307. PMID 16214946.
Neurotransmitter metabolic intermediates
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catecholamines |
Anabolism
(tyrosine→epinephrine) |
- Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine
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Catabolism/
metabolites |
dopamine: |
- DOPAL
- DOPAC
- MOPET
- Hydroxytyrosol
- 3-Methoxytyramine
- Homovanillic acid
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norepinephrine: |
- 3,4-Dihydroxymandelic acid
- Normetanephrine
- Vanillylmandelic acid
- 3-Methoxy-4-hydroxyphenylglycol
- Dihydroxyphenylethylene glycol
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epinephrine: |
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tryptophan→serotonin |
anabolism: |
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catabolism: |
- 5-Hydroxyindoleacetic acid
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serotonin→melatonin |
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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Tumor markers
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Blood |
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Endocrine |
Thyroid cancer
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- Thyroglobulin
- Medullary thyroid cancer (Calcitonin
- Carcinoembryonic antigen)
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Pheochromocytoma
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- Normetanephrine
- Enolase 2
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Neuroendocrine tumors
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- Synaptophysin
- Chromogranin A
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Neuroblastoma
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Nervous system |
Brain tumor
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Astrocytoma
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- Glial fibrillary acidic protein
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NC/Melanoma
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- S-100 protein
- Melanoma inhibitory activity
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Cardiovascular/
respiratory |
Lung cancer
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- Carcinoembryonic antigen
- Enolase 2
- Autocrine motility factor
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Hemangiosarcoma (endothelium)
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Digestive |
Colorectal cancer
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- CA19-9
- Carcinoembryonic antigen
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Pancreatic cancer
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- CA19-9
- Carcinoembryonic antigen
- CA 242
- Tumor-associated glycoprotein 72
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Hepatocellular carcinoma
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Reproductive/
urinary/
breast |
Ovarian tumor
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- Surface epithelial-stromal tumor
- EC
- EST
- Choriocarcinoma
- Dysgerminoma
- Sertoli-Leydig cell tumour
- GCT
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Testicular cancer
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- βhCG
- Alpha-fetoprotein/AFP-L3
- CD30
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Prostate cancer
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- Prostate specific antigen
- Prostatic acid phosphatase
- Glutamate carboxypeptidase II
- erbB-3 receptor
- Early prostate cancer antigen-2
- SPINK1
- GOLPH2
- PCA3
- TMPRSS2
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Germ cell tumor
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Bladder cancer
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Breast cancer
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- CA 15-3
- erbB-2 receptor
- erbB-3 receptor
- Cathepsin D
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General histology |
Sarcoma
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Carcinoma (epithelium)
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Musculoskeletal |
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UpToDate Contents
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English Journal
- Development of a diagnostic method for Parkinson's disease by reverse-phase high-performance liquid chromatography coupled with integrated pulsed amperometric detection.
- Oh M1, Huh E2, Oh MS3, Jeong JS4, Hong SP5.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2018 May 10;153:110-116. doi: 10.1016/j.jpba.2018.02.025. Epub 2018 Feb 15.
- PMID 29477128
- Chemical characterization complemented with chemometrics for the botanical origin identification of unifloral and multifloral honeys from India.
- Devi A1, Jangir J2, K A AA3.
- Food research international (Ottawa, Ont.).Food Res Int.2018 May;107:216-226. doi: 10.1016/j.foodres.2018.02.017. Epub 2018 Feb 6.
- PMID 29580480
- DNA methylation of ANKK1 and response to aripiprazole in patients with acute schizophrenia: A preliminary study.
- Miura I1, Kunii Y2, Hino M2, Hoshino H2, Matsumoto J2, Kanno-Nozaki K2, Horikoshi S2, Kaneko H2, Bundo M3, Iwamoto K3, Yabe H2.
- Journal of psychiatric research.J Psychiatr Res.2018 May;100:84-87. doi: 10.1016/j.jpsychires.2018.02.018. Epub 2018 Feb 23.
- PMID 29499474
Japanese Journal
- Pentamines as Substrate for Human Spermine Oxidase
- Takao Koichi,Shirahata Akira,Samejima Keijiro [他]
- Biological & pharmaceutical bulletin 36(3), 407-411, 2013-03
- NAID 40019588342
- Pentamines as Substrate for Human Spermine Oxidase
- 高尾 浩一,白幡 晶,鮫島 啓二郎,Casero Robert Anthony Jr.,Igarashi Kazuei,杉田 義昭
- Biological and Pharmaceutical Bulletin 36(3), 407-411, 2013-03
- … H2O2 was measured by a HPLC method that analyzed fluorescent dimers derived from the oxidation of homovanillic acid in the presence of horseradish peroxidase. …
- NAID 120005352593
- Pentamines as Substrate for Human Spermine Oxidase
- Takao Koichi,Shirahata Akira,Samejima Keijiro,Casero Jr. Robert Anthony,Igarashi Kazuei,Sugita Yoshiaki
- Biological and Pharmaceutical Bulletin 36(3), 407-411, 2013
- … H2O2 was measured by a HPLC method that analyzed fluorescent dimers derived from the oxidation of homovanillic acid in the presence of horseradish peroxidase. …
- NAID 130003382080
Related Links
- homovanillic acid /ho·mo·va·nil·lic ac·id/ (ho″mo-vah-nil´ik) a major terminal urinary metabolite, converted from dopa, dopamine, and norepinephrine. ho·mo·va·nil·lic acid (hō′mō-və-nĭl′ĭk, hŏm′ō-) n. A dopamine metabolite occurring in ...
- homovanillic acid ho·mo·va·nil·lic acid (hō'mō-və-nĭl'ĭk, hŏm'ō-) n. A dopamine metabolite occurring in human urine.
Related Pictures
![](http://msp.c.yimg.jp/image?q=tbn:ANd9GcQT2U0qTtGUXNgw-LRyFWf5H32jyszEnWDClu0S59BxWMhbt3j-Gov8_9A:http://upload.wikimedia.org/wikipedia/commons/a/aa/Homovanillic_acid.png)
![](http://msp.c.yimg.jp/image?q=tbn:ANd9GcS-e8mlhuwd6efBKlC5f71zLAg3NyOCyZ-uP_tUbUdh3HR0uggFe5At5TQ:http://www.nature.com/clpt/journal/v76/n5/images/clpt2004516f1.jpg)
![](http://msp.c.yimg.jp/image?q=tbn:ANd9GcS8fUSkhVYqvga1nIjP92lwf78wrneY39f_YGYJDab-lK_dfedudsnZ5uQ:http://www.scbt.jp/images/gels/91298.jpg)
![](http://msp.c.yimg.jp/image?q=tbn:ANd9GcTqzfzUmD2Vnmn8K5vEq5PnEoogIyM9UmBlAbT1Fb_tN09xSVHtmO2nZg:http://www.bmrb.wisc.edu/metabolomics/standards/homovanillic_acid/lit/7908.png)
![](http://msp.c.yimg.jp/image?q=tbn:ANd9GcTZEwbKF0XGdYuak69-0H0QaqtX4PhzryZOu-MkBDeFoVJ4r7FWly19Xpk:http://www.rdchemicals.com/molimg/big/7902.gif)
★リンクテーブル★
[★]
- 英
- catecholamine catecholamines CA
- 同
- カテコラミン
- 関
- 副腎髄質ホルモン
Wikipedia
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
分解産物
薬理作用
昇圧作用
臨床検査
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
[★]
- 英
- vanillylmandelic acid VMA, 3-methoxy-4-hydroxymandelic acid
- 同
- バニルマンデリン酸 vanilmandelic acid
- 関
- マンデル酸、バニリン酸、ホモバリニン酸
[★]
- 英
- homovanillic acid, HVA
- 関
臨床関連
[★]
- 同
- homovanillic acid
[★]
- 関
- homovanillic acid、HVA