Wikipedia

5-Allyloxy-AMT

(Redirected from 5-Allyloxy-αMT)

5-Allyloxy-AMT, also known as 5-allyloxy-α-methyltryptamine, is a serotonin 5-HT2 receptor agonist of the tryptamine, 5-alkyloxytryptamine, and α-alkyltryptamine families.[1]

5-Allyloxy-AMT
Clinical data
Other names5-Allyloxy-αMT; 5-AlO-AMT; 5-AlO-αMT; 5-Allyloxy-α-methyltryptamine; 2-(5-Allyloxy-1H-indol-3-yl)-1-methylethylamine; Compound 122
Drug classSerotonin 5-HT2 receptor agonist
Identifiers
  • 1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine
Chemical and physical data
FormulaC14H18N2O
Molar mass230.311 g·mol−1
3D model (JSmol)
  • C=CCOc1ccc2c(c1)c(c[nH]2)CC(N)C
  • InChI=1S/C14H18N2O/c1-3-6-17-12-4-5-14-13(8-12)11(9-16-14)7-10(2)15/h3-5,8-10,16H,1,6-7,15H2,2H3
  • Key:KHCKGFUWTBZCNH-UHFFFAOYSA-N

It is known to act as high-efficacy partial agonist or near-full agonist of the serotonin 5-HT2A receptor (EC50Tooltip half-maximal effective concentration = 162 nM; EmaxTooltip maximal efficacy = 89%) and of the serotonin 5-HT2B receptor (EC50 = 60 nM; Emax = 82%), whereas activity at the serotonin 5-HT2C receptor and other serotonin receptors was not reported.[1]

5-Allyloxy-AMT was the most potent serotonin 5-HT2A receptor agonist reported in a large series of tryptamines that was evaluated in search of potent and selective serotonin 5-HT2B receptor agonists.[1] The only exceptions were the reference serotonin 5-HT2A receptor agonists serotonin (5-HO-T) (EC50 = 79 nM; Emax = 100%) and (S)-α-methylserotonin ((S)-αMS) (EC50 = 54 nM; Emax = 103%).[1]

See also

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References

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  1. ^ a b c d Schumacher M (2008). Chirale Arylmethoxytryptamine als 5-HT2B-Rezeptoragonisten: Synthese, Analytik und in-vitro-Pharmakologie [Chiral arylmethoxytryptamines as 5-HT2B receptor agonists: synthesis, analysis, and in vitro pharmacology] (Thesis). doi:10.5283/EPUB.10667.
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