5-Hydroxyindole-3-acetic acid

Names

[ CAS No. ]:
54-16-0

[ Name ]:
5-Hydroxyindole-3-acetic acid

[Synonym ]:
5-Hydroxyindoleacetic acid
(5-Hydroxy-1H-indol-3-yl)acetic acid
2-(5-Hydroxy-1H-indol-3-yl)acetic acid
(5-hydroxyindol-3-yl)acetic acid
5-hydroxy-indole-3-acetic acid
EINECS 200-195-4
MFCD00005639
5-Hydroxyindoleacetate
5-Hydroxyindole-3-acetic Acid
1H-Indole-3-acetic acid, 5-hydroxy-
5-Hydroxyindolacetic Acid

Biological Activity

[Description]:

5-Hydroxyindole-3-acetic acid is the main metabolite of serotonin or metanephrines, which can be used as a biomarker of neuroendocrine tumors.

[Related Catalog]:

Research Areas >> Neurological Disease

Natural Products >> Acids and Aldehydes

Research Areas >> Cancer

[Target]

Human Endogenous Metabolite

[In Vitro]

5-Hydroxyindole-3-acetic acid (5HIAA) is a metabolite issued from serotonin metabolism, and the latter is synthetized from the essential amino acid tryptophan. Serotonin is mainly metabolised by monoamine oxidase in the liver and the lungs[1].

[References]

[1]. Corcuff JB, et al. Urinary sampling for 5HIAA and metanephrines determination: revisiting the recommendations. Endocr Connect. 2017 Aug;6(6):R87-R98.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.496±0.06 g/cm3

[ Boiling Point ]:
497.1±30.0 °C at 760 mmHg

[ Melting Point ]:
161-164ºC (dec.)(lit.)

[ Molecular Formula ]:
C₁₀H₉NO₃

[ Molecular Weight ]:
191.183

[ Flash Point ]:
254.4±24.6 °C

[ Exact Mass ]:
191.058243

[ PSA ]:
73.32000

[ LogP ]:
0.26

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.740

[ Water Solubility ]:
Sparingly soluble (11 g/L) (25 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL3650000

CHEMICAL NAME :: 1H-Indole-3-acetic acid, 5-hydroxy-

CAS REGISTRY NUMBER :: 54-16-0

BEILSTEIN REFERENCE NO. :: 0168797

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H9-N-O3

MOLECULAR WEIGHT :: 191.20

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1125 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 1,515,1976 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2000 mg/kg/20W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumor types after systemic administration not seen spontaneously

REFERENCE :: AICCA6 Acta Unio Internationalis Contra Cancrum. (Louvain, Belgium) V.1-20, 1936-64. For publisher information, see IJCNAW. Volume(issue)/page/year: 19,660,1963

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22;S24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
NL3650000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Permeation of Dopamine Sulfate through the Blood-Brain Barrier.

PLoS ONE 10 , e0133904, (2015)

Dopamine sulfate (DA-3- and DA-4-S) have been determined in the human brain, but it is unclear whether they are locally formed in the central nervous system (CNS), or transported into the CNS from per...

Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

The urinary ratio of 3-hydroxykynurenine/3-hydroxyanthranilic acid is an index to predicting the adverse effects of D-tryptophan in rats.

J. Nutr. Sci. Vitaminol. 60(4) , 261-8, (2014)

The adverse effects of D-tryptophan and the possibility of it being a surrogate index for predicting adverse effects in rats were investigated. Male rats were fed one of several test diets (20% casein...