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5-Methoxytryptamine

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5-Methoxytryptamine Basic information

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
  • 608-07-1
Mol File:
608-07-1.mol
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5-Methoxytryptamine Chemical Properties

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
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
16.91±0.30(Predicted)
form 
crystalline
color 
white
Merck 
13,6032
BRN 
145587
InChI
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
InChIKey
JTEJPPKMYBDEMY-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(OC)C=C2)C(CCN)=C1
CAS DataBase Reference
608-07-1(CAS DataBase Reference)
NIST Chemistry Reference
5-Methoxytryptamine(608-07-1)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36/37/38-20/21/22
Safety Statements 
36-26
WGK Germany 
3
RTECS 
NL4110000
8
HS Code 
29339900
Toxicity
LD50 intraperitoneal in mouse: 176mg/kg

MSDS

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5-Methoxytryptamine Usage And Synthesis

Description

5-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 Properties

White to tan crystalline powder

Uses

5-Methoxytryptamine (Mexamine, Methoxytryptamine) is a 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.

Definition

ChEBI: 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+).

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

General Description

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

Biochem/physiol Actions

Nonselective serotonin receptor agonist that lacks affinity for the 5-HT3 receptor.

Synthesis

5-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.

Clinical claims and research

The effects of the 5-HT receptor agonist, 5-methoxytryptamine, on plasma glucose levels were investigated in rats. 5-Methoxytryptamine induced a significant hyperglycemia above the dosage of 1 mg/kg. 5-Methoxytryptamine-induced hyperglycemia was antagonized by pretreatment with the 5-HT1 and 5-HT2 receptor antagonist, methysergide, or the 5-HT2A receptor antagonist, ketanserin, whereas the 5-HT3 and 5-HT4 receptor antagonist, tropisetron, and the 5-HT4 receptor antagonist, SDZ 205-557 (2-methoxy-4-amino-5-chloro-benzoic acid 2-(diethylamino) ethyl ester), showed no effect. In addition, the peripheral 5-HT2 receptor antagonist, xylamidine, reduced 5-methoxytryptamine-induced hyperglycemia.
Hyperglycemia induced by the 5-HT receptor agonist, 5-methoxytryptamine, in rats: involvement of the peripheral 5-HT2A receptor.

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