5-ヒドロキシインドール酢酸 5-HIAA
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"
- relating to or containing acetic acid
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
- 酢の,すっぱい
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/11/20 14:25:50」(JST)
[Wiki en表示]
| 5-Hydroxyindoleacetic acid |
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IUPAC name
2-(5-Hydroxy-1H-indol-3-yl)acetic acid
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| Identifiers |
| CAS number |
54-16-0 Y |
| PubChem |
1826 |
| ChemSpider |
1760 Y |
| KEGG |
C05635 Y |
| MeSH |
Hydroxyindoleacetic+Acid |
| ChEBI |
CHEBI:27823 Y |
| ChEMBL |
CHEMBL395915 Y |
| Jmol-3D images |
Image 1 |
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c1cc2c(cc1O)c(c[nH]2)CC(=O)O
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InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14) Y
Key: DUUGKQCEGZLZNO-UHFFFAOYSA-N Y
InChI=1/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
Key: DUUGKQCEGZLZNO-UHFFFAOYAY
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| Properties |
| Molecular formula |
C10H9NO3 |
| Molar mass |
191.18 g mol−1 |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin in the human body. In chemical analysis of urine samples, 5-HIAA is used to determine the body's levels of serotonin.
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Contents
- 1 Clinical significance
- 2 Limitations
- 3 References
- 4 Further reading
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Clinical significance
5-HIAA is tested by 24-hour urine samples combined with an acidic additive to maintain pH below 3. Certain foods and drugs are known to interfere with the measurement. 5-HIAA levels can vary depending on other complications, including tumors, renal malfunction, and small bowel resection.
Since 5-HIAA is a metabolite of serotonin, testing is most frequently performed for the diagnosis of carcinoid tumors of the enterochromaffin (Kultschitzsky) cells of the small intestine, which release large amounts of serotonin. Values greater than 25 mg per 24 hours (higher if the patient has malabsorption) are strong evidence for carcinoid.
Low levels of 5-HIAA in the cerebrospinal fluid have been associated with aggressive behavior and suicide by violent means, correlating with diminished serotonin levels.[1]
Elevated serotonin (hyperserotonemia) is one of the most common biological findings in autism[2] and 5-HIAA may be elevated in patients with autistic spectrum disorders.
Limitations
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This section does not cite any references or sources. (March 2011) |
5-HIAA may be normal with nonmetastatic carcinoid tumor and may be normal even with the carcinoid syndrome, particularly in subjects without diarrhea, because some patients with the carcinoid syndrome excrete nonhydroxylated indolic acids.
- Midgut carcinoids are most apt to produce the carcinoid syndrome with 5-HIAA elevation. Patients with renal disease may have falsely low 5-HIAA levels in the urine.
- 5-HIAA is increased in untreated patients with malabsorption, who have increased urinary tryptophan metabolites. Such patients include those with celiac disease, tropical sprue, Whipple disease, stasis syndrome, and cystic fibrosis. It is increased in those with chronic intestinal obstruction.
- Poor correlation exists between 5-HIAA level and the clinical severity of the carcinoid syndrome. 3 recent studies confirm its use as a prognostic factor in this disease.
- 5-HIAA is the major urinary metabolite of serotonin, a ubiquitous bioactive amine. Serotonin, and consequently 5-HIAA, are produced in excess by most carcinoid tumors, especially those producing the carcinoid syndrome of flushing, hepatomegaly (enlarged liver), diarrhea, bronchospasm, and heart disease. Quantitation of urinary 5-HIAA is the best test for carcinoid, but scrupulous care must be taken that specimen collection and patient preparation have been correct. Carcinoid tumors may cause increased excretion of tryptophan, 5-hydroxytryptophan and histamine as well as serotonin. Serum serotonin assay may detect some carcinoids missed by 5-HIAA assay.
The production and metabolism of serotonin, and thus 5-HIAA, is dependent upon the tissue of origin of the tumor. Tumors from midgut cells, such as ileal carcinoid usually contain and release large quantities of serotonin. These amounts may not be fully reflected in the amount of 5-HIAA in urine, because little is metabolized. Foregut tumors lack the decarboxylase enzyme necessary to convert 5-hydroxytryptophan to serotonin, resulting in minimal to no elevation in urinary 5-HIAA levels. Tumors derived from hindgut cells (rectal carcinoid) rarely produce excess serotonin or 5-HIAA. Of 75 patients with carcinoid tumors, 75% had above normal urinary 5-HIAA excretion and 64% had above normal serotonin excretion.[citation needed]
References
- ^ Thomas Bronisch: Der Suizid: Ursachen Warnsignale Prävention. 5. Auflage, C.H.Beck, München 2007, ISBN 978-3-406-55967-9, S. 63–65 (German).
- ^ Burgess, NK; Sweeten, TL; McMahon, WM; Fujinami, RS (2006). "Hyperserotoninemia and altered immunity in autism.". Journal of autism and developmental disorders 36 (5): 697–704. doi:10.1007/s10803-006-0100-7. PMID 16614791.
Further reading
- Berk, J. Edward; Bockus, Henry L. (1985). Bockus gastroenterology. Philadelphia: W.A. Saunders. ISBN 0-7216-1777-8. - Johnson HC Jr, “Urine Tests,” Volume 1, 342-7.
- Schultz AL, “5-Hydroxyindoleacetic Acid,” Methods in Clinical Chemistry, Pesce AJ and Kaplan LA, eds, St Louis, MO: Mosby-Year Book Inc, 1987, 714-20.
- Berk, J. Edward; Bockus, Henry L. (1985). Bockus gastroenterology. Philadelphia: W.A. Saunders. ISBN 0-7216-1777-8. - Warner RR, “Carcinoid Tumor,” Volume 3, 1874-6.
- Agranovich AL, Anderson GH, Manji M, Acker BD, Macdonald WC, Threlfall WJ (May 1991). "Carcinoid tumour of the gastrointestinal tract: prognostic factors and disease outcome". J Surg Oncol 47 (1): 45–52. doi:10.1002/jso.2930470111. PMID 1708841.
- Feldman JM (May 1986). "Urinary serotonin in the diagnosis of carcinoid tumors". Clin. Chem. 32 (5): 840–4. PMID 2421946. http://www.clinchem.org/cgi/pmidlookup?view=long&pmid=2421946.
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Neurotransmitter metabolic intermediates
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| catecholamines |
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Anabolism
(tyrosine→epinephrine)
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Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine
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Catabolism/
metabolites
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dopamine: DOPAL · DOPAC · MOPET · Hydroxytyrosol · 3-Methoxytyramine · Homovanillic acid
norepinephrine: 3,4-Dihydroxymandelic acid · Normetanephrine · Vanillylmandelic acid · 3-Methoxy-4-hydroxyphenylglycol · Dihydroxyphenylethylene glycol
epinephrine: Metanephrine
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| tryptophan→serotonin |
anabolism: 5-Hydroxytryptophan
catabolism: 5-Hydroxyindoleacetic acid
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| serotonin→melatonin |
Normelatonin
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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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Cholinergics
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Receptor ligands
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mAChR
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- Agonists: 77-LH-28-1
- AC-42
- AC-260,584
- Aceclidine
- Acetylcholine
- AF30
- AF150(S)
- AF267B
- AFDX-384
- Alvameline
- AQRA-741
- Arecoline
- Bethanechol
- Butyrylcholine
- Carbachol
- CDD-0034
- CDD-0078
- CDD-0097
- CDD-0098
- CDD-0102
- Cevimeline
- Choline
- cis-Dioxolane
- Ethoxysebacylcholine
- LY-593,039
- L-689,660
- LY-2,033,298
- McNA343
- Methacholine
- Milameline
- Muscarine
- NGX-267
- Ocvimeline
- Oxotremorine
- PD-151,832
- Pilocarpine
- RS86
- Sabcomeline
- SDZ 210-086
- Sebacylcholine
- Suberylcholine
- Talsaclidine
- Tazomeline
- Thiopilocarpine
- Vedaclidine
- VU-0029767
- VU-0090157
- VU-0152099
- VU-0152100
- VU-0238429
- WAY-132,983
- Xanomeline
- YM-796
Antagonists: 3-Quinuclidinyl Benzilate
- 4-DAMP
- Aclidinium Bromide
- Anisodamine
- Anisodine
- Atropine
- Atropine Methonitrate
- Benactyzine
- Benzatropine/Benztropine
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine/Dicycloverine
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine/Ethylbenztropine
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba Toxin 3
- Mamba Toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-Piperidyl Benzilate
- N-Methyl-3-Piperidyl Benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine/Hyoscine
- Solifenacin
- Telenzepine
- Tiotropium bromide
- Tolterodine
- Trihexyphenidyl
- Tripitamine
- Tropatepine
- Tropicamide
- WIN-2299
- Xanomeline
- Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine
- chlorphenamine
- cyproheptadine
- dimenhydrinate
- diphenhydramine
- doxylamine
- mepyramine/pyrilamine
- phenindamine
- pheniramine
- tripelennamine
- triprolidine, etc)
- Tricyclic Antidepressants (Amitriptyline
- doxepin
- trimipramine, etc)
- Tetracyclic Antidepressants (Amoxapine
- maprotiline, etc)
- Typical Antipsychotics (Chlorpromazine
- thioridazine, etc)
- Atypical Antipsychotics (Clozapine
- olanzapine
- quetiapine, etc)
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nAChR
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- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Lobeline
- MEM-63,908/RG-3487
- Nicotine
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- RJR-2429
- Sazetidine A
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberylcholine
- Suxamethonium/Succinylcholine
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
Antagonists: 18-Methoxycoronaridine
- α-Bungarotoxin
- α-Conotoxin
- Alcuronium
- Amantadine
- Anatruxonium
- Atracurium
- Bupropion
- Chandonium
- Chlorisondamine
- Cisatracurium
- Coclaurine
- Coronaridine
- Dacuronium
- Decamethonium
- Dextromethorphan
- Dextropropoxyphene
- Dextrorphan
- Diadonium
- DHβE
- Dimethyltubocurarine/Metocurine
- Dipyrandium
- Dizocilpine/MK-801
- Doxacurium
- Duador
- Esketamine
- Fazadinium
- Gallamine
- Hexafluronium
- Hexamethonium/Benzohexonium
- Ibogaine
- Isoflurane
- Ketamine
- Kynurenic acid
- Laudexium/Laudolissin
- Levacetylmethadol
- Malouetine
- Mecamylamine
- Memantine
- Methadone (Levomethadone)
- Methorphan/Racemethorphan
- Methyllycaconitine
- Metocurine
- Mivacurium
- Morphanol/Racemorphan
- Neramexane
- Nitrous Oxide
- Pancuronium
- Pempidine
- Pentamine
- Pentolinium
- Phencyclidine
- Pipecuronium
- Radafaxine
- Rapacuronium
- Rocuronium
- Surugatoxin
- Thiocolchicoside
- Toxiferine
- Trimethaphan
- Tropeinium
- Tubocurarine
- Vecuronium
- Xenon
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Reuptake inhibitors
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Plasmalemmal
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CHT Inhibitors
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- Hemicholinium-3/Hemicholine
- Triethylcholine
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Vesicular
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Enzyme inhibitors
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Anabolism
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ChAT inhibitors
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- 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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Catabolism
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AChE inhibitors
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BChE inhibitors
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- Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.
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Others
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Precursors
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- Choline (Lecithin)
- Citicoline
- Cyprodenate
- Dimethylethanolamine
- Glycerophosphocholine
- Meclofenoxate/Centrophenoxine
- Phosphatidylcholine
- Phosphatidylethanolamine
- Phosphorylcholine
- Pirisudanol
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Cofactors
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- Acetic acid
- Acetylcarnitine
- Acetyl-coA
- Vitamin B5 (Pantethine
- Pantetheine
- Panthenol)
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Others
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- Acetylcholine releasing agents: α-Latrotoxin
- β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime
- Obidoxime
- Pralidoxime
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UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Limited value for urinary 5-HIAA excretion as prognostic marker in gastrointestinal neuroendocrine tumours.
- Zandee WT1, Kamp K1, van Adrichem RC1, Feelders RA1, de Herder WW2.
- European journal of endocrinology.Eur J Endocrinol.2016 Nov;175(5):361-6. doi: 10.1530/EJE-16-0392. Epub 2016 Aug 4.
- OBJECTIVE: To determine if urinary 5-hydroxyindoleacetic acid (5-HIAA) excretion is of prognostic value for overall survival (OS) in patients with a gastrointestinal neuroendocrine tumour (NET) and to compare the prognostic value with patient characteristics, ENETS/WHO grading, ENETS TNM staging and
- PMID 27491374
- The Association between Elevated Levels of Peripheral Serotonin and Its Metabolite - 5-Hydroxyindoleacetic Acid and Bone Strength and Metabolism in Growing Rats with Mild Experimental Chronic Kidney Disease.
- Pawlak D1, Oksztulska-Kolanek E2, Znorko B2, Domaniewski T2, Rogalska J3, Roszczenko A3, Brzóska MM3, Pryczynicz A4, Kemona A4, Pawlak K2.
- PloS one.PLoS One.2016 Oct 6;11(10):e0163526. doi: 10.1371/journal.pone.0163526. eCollection 2016.
- Chronic kidney disease (CKD) is associated with disturbances in bone strength and metabolism. The alterations of the serotonergic system are also observed in CKD. We used the 5/6 nephrectomy model of CKD to assess the impact of peripheral serotonin and its metabolite- 5-hydroxyindoleacetic acid on b
- PMID 27711209
- Daily profiles of melatonin synthesis-related indoles in the pineal glands of young chickens (Gallus gallus domesticus L.).
- Adamska I1, Lewczuk B2, Markowska M3, Majewski PM4.
- Journal of photochemistry and photobiology. B, Biology.J Photochem Photobiol B.2016 Oct 5;164:335-343. doi: 10.1016/j.jphotobiol.2016.10.001. [Epub ahead of print]
- The aim of the present study was to characterize the daily profiles of melatonin synthesis-related indoles in the pineal glands of male Hy-Line chickens hatched in the winter and reared under controlled light (L:D 12:12) conditions. The pineal glands were isolated from 16-day-old birds immediately a
- PMID 27723491
Japanese Journal
- Time-Dependent Effects of L-Tryptophan Administration on Urinary Excretion of L-Tryptophan Metabolites
- , , ,
- Journal of Nutritional Science and Vitaminology 60(4), 255-260, 2014
- … We have previously reported that dietary supplementation with up to 5.0 g/d of L-tryptophan (L-Trp) for 21 d has no adverse effects, judging from the levels of general blood variables, in healthy women. … The subjects were randomly assigned to receive a placebo (0 g/d) or 1.0, 2.0, 3.0, 4.0, or 5.0 g/d of L-Trp for 21 d each with a 5-wk washout period between trials. …
- NAID 130004695717
- Measurement of plasma 5-hydroxyindole acetic acid by liquid chromatography tandem mass spectrometry-Comparison with HPLC methodology
- MILLER Adrian G.,BROWN Heather,DEGG Tim,ALLEN Keith,KEEVIL Brian G.
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 878(7), 695-699, 2010-03-01
- NAID 10028033488
- 動物愛護センター搬入時における子イヌの気質評価 : 性格診断テスト評価値と尿中生理指標濃度との関連性
- 藤岡 智佳,松澤 淑美,遠山 千紘 [他],植竹 勝治,江口 祐輔,田中 智夫
- 日本家畜管理学会誌・応用動物行動学会誌 45(4), 145-152, 2009-12-25
- … 搬入当日から2日目の13:00〜13:30の間に自然排尿された子イヌの尿を採取し、高速液体クロマトグラフィーを用いて尿中カテコールアミン、セロトニンおよびセロトニン代謝物(5-HIAA)濃度を測定した。 …
- NAID 110007503491
Related Links
- 2-(5-Hydroxy-1H-indol-3-yl)acetic acid ... 5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin. ... in subjects without diarrhea, because some patients with the carcinoid syndrome excrete nonhydroxylated indolic acids.
- 5-HIAA is a urine test that measures the amount of 5-hydroxyindoleacetic acid (5- HIAA) -- a breakdown product of a hormone called serotonin. This test tells how ... Alternative Names. HIAA; 5-hydroxyindole acetic acid; Serotonin metabolite ...
Related Pictures
★リンクテーブル★
[★]
- 英
- 5-hydroxyindole acetic acid, 5-HIAA
- 関
- セロトニン
[★]
- 関
- 5-ヒドロキシインドール酢酸 5-hydroxyindole acetic acid
[★]
5-ヒドロキシインドール酢酸 5-hydroxyindole acetic acid
[★]
5-ヒドロキシインドール酢酸 5-hydroxyindole acetic acid
[★]
5-ヒドロキシインドール酢酸 5-HIAA
[★]
- 関
- acetate、acetic acid、AcOH、CH3COOH