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Merck

M14935

Sigma-Aldrich

5-Methoxy-3-Indolessigsäure

98%

Synonym(e):

2-(5-Methoxy-3-indolyl)acetic acid

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About This Item

Empirische Formel (Hill-System):
C11H11NO3
CAS-Nummer:
Molekulargewicht:
205.21
Beilstein:
187161
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

98%

mp (Schmelzpunkt)

145-148 °C (dec.) (lit.)

SMILES String

COc1ccc2[nH]cc(CC(O)=O)c2c1

InChI

1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)

InChIKey

COCNDHOPIHDTHK-UHFFFAOYSA-N

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Anwendung

  • Reactant for preparation of aryloxybenzothiazoles as inhibitors of NO production
  • Reactant for preparation of transcription inhibitors of novel Gli1 as antitumor agents
  • Reactant for preparation of indole derivatives as NR2B/NMDA receptor antagonists
  • Reactant for preparation of indolyl esters and amides related to indomethacin as selective COX-2 inhibitors
  • Reactant for preparation of quinoline salicylic acid series of P-selectin antagonists
  • Reactant for preparation of prostaglandin D2 receptor antagonists

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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A M Galzin et al.
The Journal of endocrinology, 118(3), 389-397 (1988-09-01)
5-Methoxytryptamine is a potent agonist of presynaptic 5-hydroxytryptamine autoreceptors modulating serotonin release in the central nervous system. This methoxyindole can be synthesized in the pineal gland, but its presence in vivo is still controversial, probably because of rapid catabolism by
F Raynaud et al.
Journal of chromatography, 564(1), 103-113 (1991-03-08)
A liquid chromatographic analysis with electrochemical detection of 5-methoxytryptamine, 5-methoxytryptophol, 5-methoxyindoleacetic acid and melatonin is described. Optimal elution conditions were determined by studying several variables: pH, buffer salt, counter ion and organic modifier. Measurement of 5-methoxyindoles in the pineal gland
H Meissl et al.
Journal of pineal research, 17(2), 69-78 (1994-09-01)
The effect of benzodiazepines (BZP) on melatonin release was investigated in the pineal gland of the rainbow trout, Oncorhynchus mykiss, maintained under in vitro perifusion culture conditions. Melatonin and the methoxyindoles 5-methoxytryptophol (5-MTOL), 5-methoxyindoleacetic acid (5-MIAA), and 5-methoxytryptamine (5-MT) were
E S Rom-Bugoslavskaja et al.
Acta physiologica Hungarica, 70(4), 397-401 (1987-01-01)
In intact Wistar pubertal male rats held on LD 8:16 (winter) and 16:8 (summer) pineal melatonin (M) production and other pineal indoles content serotonin (S), 5-methoxytriptamine (5-MT), N-acetylserotonin (N-aS), 5-hydroxyindoleacetic acid (5-HIAA) and 5-methoxyindoleacetic acid (5-MIAA) were investigated in basic
John M Wilson et al.
Forensic science international, 148(1), 31-36 (2004-12-21)
Foxy is the colloquial name for the hallucinogen 5-ethoxy-diisopropyltryptamine (5-MeO-DIPT). A non-fatality involving a 23-year-old Caucasian man who ingested a capsule containing 5-MeO-DIPT is described. He presented to the Emergency Department, not with visual nor auditory hallucinations but with sensory

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