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M14935

Sigma-Aldrich

5-Methoxy-3-indoleacetic acid

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H11NO3
CAS Number:
3471-31-6
Molecular Weight:
205.21
Beilstein:
187161
EC Number:
222-438-3
MDL number:
MFCD00005638
UNSPSC Code:
12352100
PubChem Substance ID:
24896651
NACRES:
NA.22

Assay

98%

mp

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)

InChI key

COCNDHOPIHDTHK-UHFFFAOYSA-N

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Application

  • 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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Indole ≥99%

Sigma-Aldrich

I3408

Indole

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
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
M S Grace et al.
Neuroscience, 62(2), 615-623 (1994-09-01)
Melatonin modulates a variety of rhythmic processes in vertebrates, and is synthesized in both the retina and pineal gland. We have shown previously that retinal melatonin is deacetylated generating 5-methoxytryptamine, which is then deaminated by monoamine oxidase, producing 5-methoxyindoleacetic acid
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
J Yáñez et al.
Neurochemistry international, 27(2), 195-200 (1995-08-01)
Synthesis and release of the pineal hormone melatonin is in all vertebrates primarily regulated by the light/dark cycle. In pineal organs of teleost fish, like in other non-mammalian vertebrates, melatonin formation is regulated by a direct photoreception of the pineal
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