5-hydroxyindoleacetic acid

5-ヒドロキシインドール酢酸 5-HIAA

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

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/01/22 03:08:00」(JST)

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5-Hydroxyindoleacetic acid

Names
IUPAC name 2-(5-Hydroxy-1H-indol-3-yl)acetic acid
Identifiers
CAS Number	54-16-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27823 Y
ChemSpider	1760 Y
ECHA InfoCard	100.000.179
KEGG	C05635 Y
MeSH	Hydroxyindoleacetic+Acid
PubChem CID	1826
InChI 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
SMILES c1cc2c(cc1O)c(c[nH]2)CC(=O)O
Properties
Chemical formula	C10H9NO3
Molar mass	191.19 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin. In chemical analysis of urine samples, 5-HIAA is used to determine serotonin levels in the body.

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. The normal range is 2 to 6 mg per 24 hours.

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.

Elevated serotonin (hyperserotonemia) is one of the most common biological findings in autism and 5-HIAA may be elevated in patients with autistic spectrum disorders.

Limitations

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.

1. 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.
2. 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.
3. 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.
4. 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.

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. 

UpToDate Contents

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• 1. カルチノイド症候群および腫瘍局在の診断 diagnosis of the carcinoid syndrome and tumor localization
• 2. 小腸腫瘍の診断および病期分類 diagnosis and staging of small bowel neoplasms
• 3. 転移性の高分化型胃腸膵管系神経内分泌腫瘍：症状、予後、画像および生化学的モニタリング metastatic well differentiated gastroenteropancreatic neuroendocrine tumors presentation prognosis imaging and biochemical monitoring
• 4. 気管支神経内分泌（カルチノイド）腫瘍：疫学、危険因子、分類、組織学的検査、診断、および病期分類 bronchial neuroendocrine carcinoid tumors epidemiology risk factors classification histology diagnosis and staging
• 5. カルチノイド症候群の臨床的特徴 clinical features of the carcinoid syndrome

English Journal

• Olfactory bulb monoamine concentrations vary with time of day.

• Corthell JT, Stathopoulos AM, Watson CC, Bertram R, Trombley PQ.SourceFlorida State University, Department of Biological Science, Program in Neuroscience, Tallahassee, FL 32306, United States. Electronic address: corthell@neuro.fsu.edu.
• Neuroscience.Neuroscience.2013 Sep 5;247:234-41. doi: 10.1016/j.neuroscience.2013.05.040. Epub 2013 May 30.
• The olfactory bulb (OB) has been recently identified as a circadian oscillator capable of operating independently of the master circadian pacemaker, the suprachiasmatic nuclei of the hypothalamus. OB oscillations manifest as rhythms in clock genes, electrical activity, and odor sensitivity. Dopamine
• PMID 23727009

• Tryptophan-enriched cereal intake improves nocturnal sleep, melatonin, serotonin, and total antioxidant capacity levels and mood in elderly humans.

• Bravo R, Matito S, Cubero J, Paredes SD, Franco L, Rivero M, Rodríguez AB, Barriga C.SourceDepartment of Physiology "Neuroimmunophysiology and Chrononutrition Research Group", Faculty of Science, University of Extremadura (UEx), Badajoz, Spain, rbravo@unex.es.
• Age (Dordrecht, Netherlands).Age (Dordr).2013 Aug;35(4):1277-85. doi: 10.1007/s11357-012-9419-5. Epub 2012 May 24.
• Melatonin and serotonin rhythms, which exhibit a close association with the endogenous circadian component of sleep, are attenuated with increasing age. This decrease seems to be linked to sleep alterations in the elderly. Chrononutrition is a field of chronobiology that establishes the principle of
• PMID 22622709

• Biological basis of suicide and suicidal behavior.

• Pandey GN.SourceDepartment of Psychiatry, University of Illinois at Chicago, Chicago, IL, USA.
• Bipolar disorders.Bipolar Disord.2013 Aug;15(5):524-41. doi: 10.1111/bdi.12089. Epub 2013 Jun 15.
• OBJECTIVE: Suicide is a major public health concern as each year 30000 people die by suicide in the USA alone. In the teenage population, it is the second leading cause of death. There have been extensive studies of psychosocial factors associated with suicide and suicidal behavior. However, very li
• PMID 23773657

Japanese Journal

• 脳内5-hydroxytryptamine含量における非侵襲的マーカーとしての尿中5-hydroxyindoleacetic acid排泄量の測定 : 5,7-dihydroxytryptamineマイクロインジェクション後の脳-尿相関について

• 認知神経科学 = Japanese journal of cognitive neuroscience 19(2), 95-101, 2017-06
• NAID 40021265354

• Artificially reared mice exhibit anxiety-like behavior in adulthood

• Experimental Animals advpub(0), 267-274, 2016
• NAID 130005132736

• うつ病における血漿モノアミン代謝産物濃度の変化と臨床症状の関連の検討

• 日本生物学的精神医学会誌 25(1), 44-49, 2014
• NAID 130005395446

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• 5-hydroxyindoleacetic acid | definition of 5 ...

5-hydroxyindoleacetic acid [hi-drok″se-in″dōl-ah-se´tic] a product of serotonin metabolism excreted in large amounts in patients with carcinoid tumors. Abbreviated 5-HIAA. 5-hydroxyindoleacetic acid /5-hy·droxy·in·dole·ace·tic ac·id/ (-in″dōl-ah-se´tik ...

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