5-Methoxycarbonylamino-N-acetyltryptamine

CAS: 190277-13-5

Ref. 3D-FM25287

Product Information

• Name: 5-Methoxycarbonylamino-N-acetyltryptamine
• Synonyms: N-[3-[2-(Acetylamino)ethyl]-1H-indol-5-yl]carbamic acid methyl ester5-MCA-NATGR 135531, 5-Mca-Nat, Carbamic acid, N-[3-[2-(acetylamino)ethyl]-1H-indol-5-yl]-, methyl ester, Carbamic acid, [3-[2-(acetylamino)ethyl]-1H-indol-5-yl]-, methyl ester, Gr 135531
• CAS: 190277-13-5

Description

5-Methoxycarbonylamino-N-acetyltryptamine (5-MeO-NAT) is a tryptamine derivative that is the N-acetylated form of melatonin. It is a metabolite of melatonin, produced by the enzyme carboxylesterase, and has been found in wastewater treatment plants. 5-MeO-NAT binds to the MT2 receptor with high affinity and acts as an agonist, stimulating dopamine release in vitro. This drug has also been shown to have anti-inflammatory properties in vivo by inhibiting the production of proinflammatory cytokines in a model of tissue infection. The drug has also been shown to have a role in fetal development. 5-MeO-NAT is synthesized from serotonin by hydroxylation at position 5 on the indole ring and acetylation at position 3 on methoxybenzene ring. The synthesis proceeds via two routes: one starting from tryptophan and another

• Brand: Biosynth

Chemical properties

• Molecular weight: 275.3 g/mol
• Formula: C₁₄H₁₇N₃O₃
• Purity: Min. 95%
• Color/Form: Brown Solid
• InChI: InChI=1S/C14H17N3O3/c1-9(18)15-6-5-10-8-16-13-4-3-11(7-12(10)13)17-14(19)20-2/h3-4,7-8,16H,5-6H2,1-2H3,(H,15,18)(H,17,19)
• InChI key: InChIKey=MPZVHKLZCUEJFO-UHFFFAOYSA-N
• SMILES: COC(=O)Nc1ccc2[nH]cc(CCNC(C)=O)c2c1