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Merck

286583

Sigma-Aldrich

5-Methoxytryptamine

97%

Sinónimos:

2-(5-Methoxyindol-3-yl)ethylamine, 3-(2-Aminoethyl)-5-methoxyindole, 5-MOT, 5-Methoxyindole-3-ethanamine, Deacetylmelatonin, NSC 56422

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About This Item

Fórmula empírica (notación de Hill):
C11H14N2O
Número de CAS:
Peso molecular:
190.24
Beilstein:
145587
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

97%

Formulario

solid

mp

121-123 °C (lit.)

grupo funcional

amine

cadena SMILES

COc1ccc2[nH]cc(CCN)c2c1

InChI

1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

Clave InChI

JTEJPPKMYBDEMY-UHFFFAOYSA-N

Información sobre el gen

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Descripción general

The protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied.

Aplicación

5-Methoxytryptamine was used as an agonist in the study of pharmacological profile of the 5-hydroxytryptamine 1 receptor.
Reactant for preparation of:
  • Carboline disaccharide domain of shishijimicin A
  • Melatonin analogs for the reduction of intraocular pressure
  • 5-HT4 receptor ligands
  • inhibitors of sortase A and isocitrate lyase
  • Therapeutic agents for treatment of ischemia/reperfusion (I/R) injury
  • Aurora and epidermal growth factor receptor kinase inhibitors
  • Agents for the treatment of human papillomavirus infection
  • Manzamine analogues for the control of neuroinflammation and cerebral infections
  • Inhibitors of pro-inflammatory cytokines
  • Tacrine-melatonin hybrids as multifunctional agents for alzheimer′s disease

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Amir Hanna-Elias et al.
European journal of medicinal chemistry, 44(7), 2952-2959 (2009-02-19)
Twenty-three indole-3-methanamines were designed, synthesized and evaluated as ligands for the 5-HT(4) receptor. Compounds I-d, I-j, I-o, I-q and I-u showed good affinity at 100 microM and I-o was found to be only 5-fold less potent than the agonists serotonin
Melatonin and its metabolites ameliorate ultraviolet B-induced damage in human epidermal keratinocytes.
Janjetovic Z, Nahmias ZP, Hanna S, et al.
Journal of Pineal Research, 57(1), 90-102 (2014)
R Hardeland
Reproduction, nutrition, development, 39(3), 399-408 (1999-07-27)
Melatonin seems to be an almost ubiquitous substance, which has been detected not only in metazoans, but also in all major non-metazoan taxa investigated, including bacteria, dinoflagellates, euglenoids, trypanosomids, fungi, rhodophyceans, pheophyceans, chlorophyceans and angiosperms. Despite its vast abundance, little
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Journal of pharmacological sciences, 106(1), 2-8 (2008-01-17)
Psychostimulants including amphetamines and cocaine, opioids including morphine, and some recreational drugs share the ability to cause drug dependence and addiction. Although these drugs of abuse primarily act on distinct molecular targets, such as monoamine transporters or receptors, they finally
Melissa M Martin et al.
Physiology & behavior, 105(2), 529-535 (2011-10-01)
Autistic spectrum disorders (ASDs) are classified as pervasive developmental disorders characterized by abnormalities in various cognitive and behavioral functions. Although exact underlying causes are still unknown, nearly 30% of autistic patients show elevated blood levels of serotonin (5-HT) and, therefore

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