5-Allyloxy-AMT

5-Allyloxy-AMT

Clinical data
Other names	5-Allyloxy-αMT; 5-AlO-AMT; 5-AlO-αMT; 5-Allyloxy-α-methyltryptamine; 2-(5-Allyloxy-1H-indol-3-yl)-1-methylethylamine; Compound 122
Drug class	Serotonin 5-HT2 receptor agonist
Identifiers
IUPAC name 1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine
Chemical and physical data
Formula	C14H18N2O
Molar mass	230.311 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C=CCOc1ccc2c(c1)c(c[nH]2)CC(N)C
InChI 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

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]

It is known to act as high-efficacy partial agonist or near-full agonist of the serotonin 5-HT_2A receptor (EC₅₀Tooltip half-maximal effective concentration = 162 nM; E_maxTooltip maximal efficacy = 89%) and of the serotonin 5-HT_2B receptor (EC₅₀ = 60 nM; E_max = 82%), whereas activity at the serotonin 5-HT_2C receptor and other serotonin receptors was not reported.^[1]

5-Allyloxy-AMT was the most potent serotonin 5-HT_2A receptor agonist reported in a large series of tryptamines that was evaluated in search of potent and selective serotonin 5-HT_2B receptor agonists.^[1] The only exceptions were the reference serotonin 5-HT_2A receptor agonists serotonin (5-HO-T) (EC₅₀ = 79 nM; E_max = 100%) and (S)-α-methylserotonin ((S)-αMS) (EC₅₀ = 54 nM; E_max = 103%).^[1]

See also

• 5-Ethoxy-AMT
• 5-Ethoxy-DMT
• 5-Methoxy-AMT
• 5-(Nonyloxy)tryptamine
• 5-Benzyloxytryptamine
• BW-723C86

References

1. 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.

External links

• 5-Allyloxy-AMT - Isomer Design