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286583

Sigma-Aldrich

5-Methoxytryptamine

97%

Synonym(s):

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

Empirical Formula (Hill Notation):
C11H14N2O
CAS Number:
608-07-1
Molecular Weight:
190.24
Beilstein:
145587
EC Number:
210-153-7
MDL number:
MFCD00005662
UNSPSC Code:
12352100
PubChem Substance ID:
24857245
NACRES:
NA.22

Assay

97%

form

solid

mp

121-123 °C (lit.)

SMILES string

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

InChI key

JTEJPPKMYBDEMY-UHFFFAOYSA-N

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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)

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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)
Rut Vleugels et al.
PloS one, 8(5), e65052-e65052 (2013-06-07)
Serotonin (5-hydroxytryptamine, 5-HT) is known for its key role in modulating diverse physiological processes and behaviors by binding various 5-HT receptors. However, a lack of pharmacological knowledge impedes studies on invertebrate 5-HT receptors. Moreover, pharmacological information is urgently needed in
Brian J Prendergast
Endocrinology, 151(2), 714-721 (2009-12-08)
Environmental day length drives nocturnal pineal melatonin secretion, which in turn generates or entrains seasonal cycles of physiology, reproduction, and behavior. In mammals, melatonin (MEL) binds to a number of receptor subtypes including high-affinity (MT1 and MT2) and low-affinity (MT3
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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