バニリルマンデル酸 VMA
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)』「2015/06/11 11:46:57」(JST)
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Vanillylmandelic acid
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Names |
IUPAC name
(RS)-hydroxy(4-hydroxy-3-methoxy-phenyl)acetic acid
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Other names
α,4-Dihydroxy-3-methoxybenzeneacetic acid, VMA, Vanillomandelic acid, Vanillylmandelic acid, Vanilmandelic acid
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Identifiers |
Beilstein Reference
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2213227 |
CAS Registry Number
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55-10-7 Y |
ChEBI |
CHEBI:20106 Y |
ChemSpider |
1207 Y |
EC number |
201-701-6 |
InChI
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InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13) Y
Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N Y
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InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
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Jmol-3D images |
Image
Image |
MeSH |
Vanilmandelic+acid |
PubChem |
1245 |
SMILES
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COC1=C(C=CC(=C1)C(C(=O)O)O)O
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O=C(O)C(O)c1cc(OC)c(O)cc1
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Properties |
Chemical formula
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C9H10O5 |
Molar mass |
198.173 g/mol |
Appearance |
White powder |
Melting point |
133 °C (271 °F; 406 K) |
Hazards |
Safety data sheet |
MSDS at Sigma Aldrich |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is: Y/N?) |
Infobox references |
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Vanillyl mandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings[1] and is an end-stage metabolite of the catecholamines, epinephrine, and norepinephrine. It is produced via intermediary metabolites.
Contents
- 1 Chemical Synthesis
- 2 Biological Elimination
- 3 Clinical significance
- 4 References
Chemical Synthesis
VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla.[1] Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide.
Biological Elimination
VMA is found in the urine, along with other catecholamine metabolites, including homovanillic acid (HVA), metanephrine, and normetanephrine. In timed urine tests the quantity excreted (usually per 24 hours) is assessed along with creatinine clearance, and the quantity of cortisols, catecholamines, and metanephrines excreted is also measured.
Norepinephrine degradation. Vanillylmandelic acid is shown at top right. Enzymes are shown in boxes.
[2]
Clinical significance
Urinary VMA is elevated in patients with tumors that secrete catecholamines.[3]
These urinalysis tests are used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. These tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions.
Norepinephrine is metabolised into normetanephrine and VMA. Norepinephrine is one of the hormones produced by the adrenal glands, which are found on top of the kidneys. These hormones are released into the blood during times of physical or emotional stress, which are factors that may skew the results of the test.[citation needed]
References
- ^ a b Fatiadi, Alexander; and Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of Standards - A. Physics and Chemistry 78A (3): 411–412. doi:10.6028/jres.078A.024. Retrieved 19 December 2013.
- ^ 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.
- ^ Magera MJ, Thompson AL, Matern D, Rinaldo P (May 2003). "Liquid chromatography-tandem mass spectrometry method for the determination of vanillylmandelic acid in urine". Clin. Chem. 49 (5): 825–6. doi:10.1373/49.5.825. PMID 12709381.
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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Index of the central nervous system
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Description |
- Anatomy
- meninges
- cortex
- association fibers
- commissural fibers
- lateral ventricles
- basal ganglia
- diencephalon
- mesencephalon
- pons
- cerebellum
- medulla
- spinal cord
- Physiology
- Development
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Disease |
- Cerebral palsy
- Meningitis
- Demyelinating diseases
- Seizures and epilepsy
- Headache
- Stroke
- Sleep
- Congenital
- Injury
- Neoplasms and cancer
- Other
- Symptoms and signs
- head and neck
- eponymous
- lesions
- Tests
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Treatment |
- Procedures
- Drugs
- general anesthetics
- analgesics
- addiction
- epilepsy
- cholinergics
- migraine
- Parkinson's
- vertigo
- other
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Tumor markers
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Blood |
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Endocrine |
Thyroid cancer |
- Thyroglobulin
- Medullary thyroid cancer (Calcitonin
- Carcinoembryonic antigen)
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Pheochromocytoma |
- Normetanephrine
- Enolase 2
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Neuroendocrine tumors |
- Synaptophysin
- Chromogranin A
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Neuroblastoma |
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Nervous system |
Brain tumor |
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Astrocytoma |
- Glial fibrillary acidic protein
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NC/Melanoma |
- S100 protein
- Melanoma inhibitory activity
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Cardiovascular/
respiratory |
Lung cancer |
- Carcinoembryonic antigen
- Enolase 2
- Autocrine motility factor
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Hemangiosarcoma (endothelium) |
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Digestive |
Colorectal cancer |
- CA19-9
- Carcinoembryonic antigen
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Pancreatic cancer |
- 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 |
- Surface epithelial-stromal tumor
- EC
- EST
- Choriocarcinoma
- Dysgerminoma
- Sertoli-Leydig cell tumour
- GCT
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Testicular cancer |
- βhCG
- Alpha-fetoprotein/AFP-L3
- CD30
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Prostate cancer |
- Prostate-specific antigen
- Prostatic acid phosphatase
- Glutamate carboxypeptidase II
- erbB-3 receptor
- Early prostate cancer antigen-2
- SPINK1
- GOLM1
- PCA3
- TMPRSS2
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Germ cell tumor |
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Bladder cancer |
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Breast cancer |
- 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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Index of neoplasms and cancer
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Description |
- Tumor suppressing and oncogenes
- Tumor markers
- Carcinogen
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Disease |
- Neoplasms and cancer
- Symptoms and signs
- Paraneoplastic
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Treatment |
- Radiotherapy
- Drugs
- Immunotherapy
- intracellular chemotherapeutics
- extracellular chemotherapeutics
- adjuvant detoxification
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UpToDate Contents
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English Journal
- Pheochromocytoma presenting with remote bony recurrence twenty years after initial surgery: detection with 68Ga-DOTANOC PET/CT.
- Parida GK1, Dhull VS, Sharma P, Bal C, Kumar R.Author information 1From the Department of Nuclear Medicine, All India Institute of Medical sciences, New Delhi, India.AbstractPheochromocytomas are rare tumors which can be malignant in 10% of cases. We present the case of a 75-year-old woman who presented with headache and palpitation for 1 year. She had a past history of right adrenalectomy for pheochromocytoma 20 years back. In between, the patient was asymptomatic. Twenty-four-hour urinary vanillylmandelic acid was raised. Noncontrast CT and ultrasound of abdomen were unremarkable. The patient underwent 68Ga-DOTANOC PET/CT that showed metastasis to left ilium, which was confirmed on biopsy.
- Clinical nuclear medicine.Clin Nucl Med.2014 Apr;39(4):365-6. doi: 10.1097/RLU.0b013e31828e98f0.
- Pheochromocytomas are rare tumors which can be malignant in 10% of cases. We present the case of a 75-year-old woman who presented with headache and palpitation for 1 year. She had a past history of right adrenalectomy for pheochromocytoma 20 years back. In between, the patient was asymptomatic. Twe
- PMID 23640231
- Monoamine metabolites in ventricular CSF of children with posterior fossa tumors: correlation with tumor histology and cognitive functioning.
- Varela M1, Alexiou GA, Liakopoulou M, Papakonstantinou E, Pitsouni D, Alevizopoulos GA.Author information 1Department of Neurosurgery.AbstractObject The biogenic amines (dopamine, epinephrine, norepinephrine, and serotonin) are involved in the regulation of multiple neuronal functions, and changes in monoamine concentrations in the CSF have been detected in several disorders. The aim of the present study was to investigate the role of biogenic amines in the ventricular CSF of children suffering from posterior fossa tumors and their possible correlation with tumor histology and cognitive functioning. Methods Twenty-two children with posterior fossa tumors who were treated surgically at Children's Hospital "Agia Sofia" were studied. Patients ranged in age from 5.5 to 15 years. The study population included patients who suffered from hydrocephalus and were treated by ventriculoperitoneal shunt placement. During the operation for shunt placement, a CSF sample was obtained for the assessment of 3-methoxy-4-hydroxyphenylglycol (MHPG), homovanillic acid (HVA), and 5-hydroxyindoleacetic acid (5-HIAA). Simultaneously, a blood sample was also obtained for assessment of the same metabolites in the serum. The concentration of vanillylmandelic acid (VMA) was evaluated in 24-hour urine samples in 11 patients. Cerebrospinal fluid from a control group of children was also studied. Executive functions were assessed using the short form of the Wechsler Intelligence Scale for Children (WISC). Results Twelve patients suffered from astrocytomas, 9 from medulloblastomas, and 1 from an ependymoma. The MHPG concentration in CSF was significantly higher in patients with astrocytomas compared with patients with medulloblastomas. Twenty-four-hour urine samples of VMA were significantly higher in patients with astrocytomas compared with patients with medulloblastomas. The MHPG concentration in CSF was negatively correlated with the verbal scale of the WISC and there was a trend toward a significant negative correlation with the total WISC score. Homovanillic acid in CSF was positively correlated with the performance scale of the WISC. There was a significant correlation between HVA and MHPG levels in CSF. The CSF concentration of 5-HIAA was significantly correlated with the HVA concentration in serum. Twenty-four-hour urine VMA samples were statistically significantly correlated with HVA concentration in both CSF and serum, with MHPG in CSF, and with 5-HIAA in serum. Conclusions This study showed that children with posterior fossa tumors have differences in the levels of monoamine metabolites in CSF. Further studies with a larger number of patients are obviously needed to verify these observations as well as studies to correlate the monoamine metabolite levels with the neuropsychological and behavioral findings in children with posterior fossa tumors.
- Journal of neurosurgery. Pediatrics.J Neurosurg Pediatr.2014 Apr;13(4):375-9. doi: 10.3171/2014.1.PEDS13425. Epub 2014 Feb 21.
- Object The biogenic amines (dopamine, epinephrine, norepinephrine, and serotonin) are involved in the regulation of multiple neuronal functions, and changes in monoamine concentrations in the CSF have been detected in several disorders. The aim of the present study was to investigate the role of bio
- PMID 24559277
- Diagnostic Challenge of Pheochromocytoma in a Patient Receiving Levodopa for Parkinson's Disease.
- Shimodaira M, Niwa T, Nakajima K, Kobayashi M, Shimodaira M, Niwa T, Nakajima K, Kobayashi M.Author information The Department of Internal Medicine, Iida Municipal Hospital, Nagano, Japan.AbstractObjective The diagnosis of pheochromocytoma in patients receiving levodopa is challenging because the standard diagnostic biochemical tests are considered to be confounded by dopaminergic therapy. We aim to showcase our experience with the diagnosis of pheochromocytoma in a known case of Parkinson's disease receiving levodopa.Methods We present a case of an elderly male who was diagnosed as pheochromocytoma while receiving dopaminergic therapy for Parkinson's disease.Results A 75 year-old man presented with vague abdominal symptoms. Computed tomography revealed a 3.5 x 3.2-cm right adrenal mass with a well-defined margin. As revealed by magnetic resonance imaging, the mass was hypointense on T1-weighted and hyperintense on T2-weighted images. Biochemical tests revealed elevated levels of urinary dopamine, which was considered to be caused by levodopa therapy. However, the concurrent elevation of urinary adrenaline, and metanephrine, vanillylmandelic acid levels suggested an underlying of pheochromocytoma. 123I-metaiodobenzylguanidine (123I-MIBG) scintigraphy performed under levodopa therapy, showed positive tracer uptake in the right adrenal gland. Histopathology of the adrenalectomy specimen confirmed the diagnosis of pheochromocytoma.Conclusion Our experience with the present case indicates that although the standard diagnostic biochemical tests for pheochromocytoma may be confounded by dopaminergic therapy, 123I-MIBG scintigraphy has diagnostic value for confirming pheochromocytoma even in patients receiving dopaminergic therapy.
- Endocrine practice : official journal of the American College of Endocrinology and the American Association of Clinical Endocrinologists.Endocr Pract.2014 Mar 18:1-14. [Epub ahead of print]
- Objective The diagnosis of pheochromocytoma in patients receiving levodopa is challenging because the standard diagnostic biochemical tests are considered to be confounded by dopaminergic therapy. We aim to showcase our experience with the diagnosis of pheochromocytoma in a known case of Parkinson's
- PMID 24641926
Japanese Journal
- 家族歴にMenkes病を認める新生児3例の臨床像の検討
- 八木 麻理子,楠 典子,李 知子,粟野 宏之,森岡 一朗,児玉 浩子,竹島 泰弘,飯島 一誠
- 脳と発達 46(1), 26-29, 2014
- 【目的】Menkes病 (MD) 早期診断の手がかりを検討する. 【方法】家族歴にMDを認め罹患リスクのある男児3例 (罹患児1例, 非罹患児2例) の新生児期の臨床像を比較した. 【結果】MDに特徴的なkinky hairは, 出生直後は極軽微で見逃す危険性があった. 血清銅は, 罹患児では経時的に低下したが, 非罹患児では上昇した. MDで上昇するとされる尿HVA/VMA比は, 罹患児ではc …
- NAID 130005005676
- New semi-quantitative ^<123>I-MIBG estimation method compared with scoring system in follow-up of advanced neuroblastoma : utility of total MIBG retention ratio versus scoring method
- SANO Yuko,OKUYAMA Chio,IEHARA Tomoko,MATSUSHIMA Shigenori,YAMADA Kei,HOSOI Hajime,NISHIMURA Tsunehiko
- Annals of nuclear medicine 26(6), 462-470, 2012-07-01
- NAID 10030949416
- 住吉 崇幸,清水 洋祐,井上 貴博 [他]
- 泌尿器科紀要 57(8), 429-433, 2011-08
- … A more detailed examination at our hospital revealed elevation of vanillylmandelic acid in urine and 131Imetaiodobenzylguanidine uptake in the tumor. …
- NAID 40018942640
Related Links
- vanillylmandelic acid [vah-nil″il-man-del´-ik] VMA; the primary end-product of catecholamine metabolism excreted in the urine. Urinary VMA levels are used in screening patients for pheochromocytoma. va·nil·lyl·man·del·ic ac·id (VMA),
- vanillylmandelic acid [vah-nil″il-man-del´-ik] VMA; the primary end-product of catecholamine metabolism excreted in the urine. Urinary VMA levels are used in screening patients for pheochromocytoma. va·nil·lyl·man·del·ic ac·id (VMA),
Related Pictures
★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
[★]
- 英
- vanillylmandelic acid, VMA
- 同
- バニルマンデリン酸, 4-hydroxy-3-methoxymandelic acid
[show details]
[★]
バニリルマンデル酸 vanillylmandelic acid