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Product Name:5-Methoxytryptamine
Synonyms:1H-Indole-3-ethanamine, 5-methoxy-;3-(2-aminoethyl)-5-methoxy-indol;5-methoxy-1h-indole-3-ethanamin;5MOT;Ethanamine,2-(5-methoxy-3-indolyl)-;Indole, 3-(2-aminoethyl)-5-methoxy-;Meksamin (free base);Methoxytryptamine
CAS:608-07-1
MF:C11H14N2O
MW:190.24
EINECS:210-153-7
Product Categories:Agonists;Amines;Heterocycles;Indole Derivatives;Intermediates & Fine Chemicals;Neurochemicals;Indole/indoline/oxindole;Indole and Indoline;Pharmaceuticals;Bioactive Small Molecules;Building Blocks;C11;Cell Biology;Chemical Synthesis;PHARMACEUTICAL INTERMEDIATES;Tryptamines;pharmacetical;Indoline & Oxindole;Indoles;Building Blocks;Heterocyclic Building Blocks;Non-Chiral heterocyclic compounds;Heterocyclic Building Blocks;M
Mol File:608-07-1.mol
Melting point 121-123 °C (lit.)
Boiling point 325.75°C (rough estimate)
density 1.0815 (rough estimate)
refractive index 1.5700 (estimate)
storage temp. 2-8°C
form crystalline
pka16.91±0.30(Predicted)
color white
Merck 13,6032
Description5-Methoxytryptamine (5-MT), also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels.It is biosynthesized via the deacetylation of melatonin in the pineal gland.
The protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied.
Melatonin and its metabolites ameliorate ultraviolet B-induced damage in human epidermal keratinocytes.
Chemical PropertiesWhite to tan crystalline powder
UsesA tryptamine derivative that is closely related to the neurotransmitter Melatonin (M215000) and Serotonin (S274980). It acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors but has no affinity for the 5-HT3 receptor.
Uses5-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
Uses5HT agonist
DefinitionChEBI: 5-methoxytryptamine is a member of the class of tryptamines that is the methyl ether derivative of serotonin. It has a role as a serotonergic agonist, a human metabolite, a mouse metabolite, a 5-hydroxytryptamine 2A receptor agonist, a 5-hydroxytryptamine 2C receptor agonist, a 5-hydroxytryptamine 2B receptor agonist, an antioxidant, a radiation protective agent, a neuroprotective agent and a cardioprotective agent. It is a member of tryptamines, an aromatic ether and a primary amino compound. It derives from a serotonin. It is a conjugate base of a 5-methoxytryptamine(1+).
General DescriptionThe protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied.
Biochem/physiol ActionsNonselective serotonin receptor agonist that lacks affinity for the 5-HT3 receptor.
Chemical Synthesis5-Methoxytryptamine (358) was synthesized from 3-(2-iodoethyl)-5-methoxyindole (176) by reaction with 1-methyl-benzylamine (MeCN, 24 h, RT) and subsequent catalytic debenzylation of 44 (H2, Pd/C, EtOH, 24 h, RT, 4 bar). The resulting 5-methoxytryptamine (358 was then reacted with 4-bromobenzoylchloride (THF, NEt3, RT, ON) and the resulting tryptamide 359 was reduced with aluminum hydride to N-(4-bromobenzyl)-5-methoxytryptamine (19) (LiAlH4, AlCl3, Et2O, 5 h, RT), which was isolated as its hydrogen oxalate salt.
