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Merck

286583

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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Fórmula empírica (notación de Hill):
C11H14N2O
Número CAS:
608-07-1
Peso molecular:
190.24
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24857245
EC Number:
210-153-7
Beilstein/REAXYS Number:
145587
MDL number:
MFCD00005662
Assay:
97%
Form:
solid

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InChI key

JTEJPPKMYBDEMY-UHFFFAOYSA-N

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

SMILES string

COc1ccc2[nH]cc(CCN)c2c1

assay

97%

form

solid

drug control

Új pszichoaktív anyag / New psychoactive substance (Hungary), 78/2022. (XII. 28.) BM rendelet

mp

121-123 °C (lit.)

functional group

amine

Quality Level

200

Gene Information

human ... HTR1A(3350), HTR2A(3356), HTR2C(3358)
rat ... Htr2a(29595), Htr2c(25187), Htr7(65032)

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General description

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

Application

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCN1828
BCCM2087
BCCL6994
BCCJ5354
BCCG8355

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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)
Takayuki Nakagawa et al.
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
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
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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