5-Hydroxyindoleacetic Acid
5-HIAA · HIAA · 2-(5-hydroxy-1H-indol-3-yl)acetic acid · 5-oxyindoleaceticacid · 5-HYDROXY-3-INDOLEACETIC ACID · 5&＃039 · 5-HO-IAA · NSC 90432
식별자 및 물리적 특성
| CAS No. | 54-16-0 |
|---|---|
| 분자식 | C10H9NO3 |
| 평균 분자량 | 191.18 g/mol |
| 단동위원소 질량 | 191.05824315 g/mol |
| SMILES | O=C(O)Cc1c[nH]c2ccc(O)cc12 |
| InChIKey | DUUGKQCEGZLZNO-UHFFFAOYSA-N |
| PubChem CID | 1826 |
| ChEMBL | CHEMBL395915 |
| ChEBI | CHEBI:27823 |
| EC No. | 200-195-4 |
| DTXSID | DTXSID50861582 |
화학 및 물리적 성질
| XLogP | 1.1 |
|---|---|
| 극성 표면적 | 73.3 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 231 |
| 용해도 | 24 mg/mL>28.7 [ug/mL] (The mean of the results at pH 7.4)에탄올(50mg/ml)에 용해됩니다. |
| 녹는점 | 161 - 163 °C161-164 °C (dec.) (lit.) |
| Physical Description | Light red crystalline solid[Sigma-Aldrich MSDS] |
| Collision Cross Section | 148.4 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]137.1 Ų [M-H]- [CCS Type: DT140.9 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]141.1 Ų [M+H]+148.6 Ų [M+Na]+137.3 Ų [M-H]- |
| 끓는 점 | 326.92°C (rough estimate) |
| 밀도 | 1.2722 (rough estimate) |
| 굴절률 | 1.5310 (estimate) |
| 저장 조건 | -20°C |
| pKa(산도 계수) | 4.54±0.30(Predicted) |
| 물리적 상태 | 수정 같은 |
| 색상 | 황백색에서 보라색까지 |
| BRN | 168797 |
| 안정성 | 공기 민감성, 빛 민감성 |
| 주요 응용 | 임상 시험 |
| 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) |
| InChIKey | DUUGKQCEGZLZNO-UHFFFAOYSA-N |
| SMILES | OC(=O)Cc1c[nH]c2ccc(O)cc12 |
화학적 성질
beige crystalline powder
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: 1H-Indole-3-acetic acid, 5-hydroxy-5-Hydroxyindol-3-ylacetic acid: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia |
| 유해성 요약 | Causes somnolence in intraperitoneal lethal-dose studies of mice (LD50 = 1,125 mg/kg)[RTECS] May cause irritation[Sigma-Aldrich MSDS] See Indole-3-butyric acid. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (100%) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | NL3650000 |
| 관세 코드 | 29339980 |
| 안전 문구(S) | 22-24/25 |
| F 고인화성물질 | 8-10-23 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; ). It is formed when 5-HT is metabolized by monamine oxidase and aldehyde dehydrogenase in the liver. 5-HIAA is excreted in urine and has been used as a biomarker for detection of neuroendocrine tumors and an internal standard for the quantification of serotonin metabolism in rat brain using mass spectrometry. 5-HIAA has also been associated with autism, insomnia, and chronic migraine.
용도
5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.
일반 설명
5-Hydroxyindole-3-acetic acid (5-HIAA) is the catabolic end product of serotonin pathway. 5-HIAA is present in body fluids like cerebrospinal fluid (CSF), blood and urine. The expression levels of 5-HIAA is different among the normal and cancer patients. Sepiapterin reductase deficiency results in low level of 5-HIAA in CSF. 5-HIAA level is low in CSF in patients with bipolar 1 disorder with childhood attention-deficit hyperactivity disorder (ADHD).