5-Methoxytryptamine

Base Information

• Chemical Name: 5-Methoxytryptamine
• CAS No.: 608-07-1
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.245
• Hs Code.: 29339900
• European Community (EC) Number: 210-153-7
• NSC Number: 56422
• UNII: 3VMW6141KC
• DSSTox Substance ID: DTXSID60209638
• Nikkaji Number: J7.009B
• Wikipedia: 5-methoxytryptamine
• Wikidata: Q4352011
• Pharos Ligand ID: Y6SQ2W7KNWCG
• Metabolomics Workbench ID: 38466
• ChEMBL ID: CHEMBL8165
• Mol file: 608-07-1.mol

Synonyms:5 Methoxytryptamine;5-Methoxytryptamine;Meksamine;Methoxytryptamine;Mexamine

Chemical Property of 5-Methoxytryptamine

Chemical Property:

• Appearance/Colour: White to tan crystalline powder
• Melting Point: 245-250 °C (dec.)(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 380oC
• PKA: 16.91±0.30(Predicted)
• PSA: 51.04000
• Density: 1.0815 (rough estimate)
• LogP: 2.37800
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 190.110613074
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxytryptamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2CCN
• 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.
• 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.

Technology Process of 5-Methoxytryptamine

There total 52 articles about 5-Methoxytryptamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-ethoxycarbonyl-3-(2-phthalimidoethyl)-5-methoxyindole (55747-53-0) → 2-(5-methoxyindol-3-yl)ethylamine (608-07-1)

Guidance literature:

2-ethoxycarbonyl-3-(2-phthalimidoethyl)-5-methoxyindole; With water; sodium hydroxide; at 88 - 90 ℃;

With hydrogenchloride; In water; at 10 - 110 ℃; Temperature;

Reference yield: 99.0%

5-methoxy-3-(2-nitroethyl)-1H-indole (68935-49-9) → 2-(5-methoxyindol-3-yl)ethylamine (608-07-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃;

DOI:10.1016/j.cclet.2010.05.012

Reference yield: 99.0%

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate (67199-10-4) → 2-(5-methoxyindol-3-yl)ethylamine (608-07-1)

Guidance literature:

With sodium hydroxide; In methanol; for 4h; Heating;

DOI:10.3987/COM-00-8930

upstream raw materials:

5-methoxylindole

methyl magnesium iodide

diethyl ether

chloroacetonitrile

Downstream raw materials:

6-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

N-Chloracetyl-5-methoxytryptamin

(1R,2'S,4'R,5'R)-1-(5'-benzoylamino-4'-methyl-1',3'-dioxan-2'-yl)methyl-6-methoxy-1,2,3,4-tetrahydrocarboline-3-carboline

2-(2-chloro-ethyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-benzamide

Refernces

• 1、 Somei, Masanori,Oshikiri, Naoki,Hasegawa, Masakazu,Yamada, Fumio. "Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (±)-3a,3a'-bispyrrolo[2,3-b]indoles". . p. 1237 - 1242. Retrieved 1999.
• 2、 Cheng, Didi,Li, Jingyi,Li, Yujin,Ling, Fei,Liu, Lei,Liu, Tao,Zhong, Weihui. "Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source". supporting information. p. 4107 - 4113. Retrieved 2021/06/17.
• 3、 Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta. "N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential". . . Retrieved 2021/08/17.