1-Propyl-5-MeO-AMT

1-Propyl-5-MeO-AMT, also known as 1-propyl-5-methoxy-α-methyltryptamine, is a serotonin receptor modulator of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families.^[1][2][3] It is the 1-propyl derivative of 5-methoxy-α-methyltryptamine (5-MeO-AMT).^[3]

Other names1-Propyl-5-MeO-DMT; 1-Pr-5-MeO-DMT; 1-Propyl-5-methoxy-α-methyltryptamine; N1-n-Propyl-5-methoxy-α-methyltryptamine

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor modulator

PubChem CID

• 14739627

ChemSpider

• 23182714

Quick facts Clinical data, Other names ...

1-Propyl-5-MeO-AMT

Clinical data
Other names	1-Propyl-5-MeO-DMT; 1-Pr-5-MeO-DMT; 1-Propyl-5-methoxy-α-methyltryptamine; N1-n-Propyl-5-methoxy-α-methyltryptamine
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor modulator
Identifiers
IUPAC name 1-(5-methoxy-1-propylindol-3-yl)propan-2-amine
PubChem CID	14739627
ChemSpider	23182714
ChEMBL	ChEMBL439773
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN1C=C(C2=C1C=CC(=C2)OC)CC(C)N
InChI InChI=1S/C15H22N2O/c1-4-7-17-10-12(8-11(2)16)14-9-13(18-3)5-6-15(14)17/h5-6,9-11H,4,7-8,16H2,1-3H3 Key:DAGLCFOMYRIMJJ-UHFFFAOYSA-N

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Whereas most tryptamines are highly non-selective in terms of binding to serotonin receptors, 1-propyl-5-MeO-AMT shows selectivity for the serotonin 5-HT_2A receptor.^[1][2][3] Its affinities (K_i) for serotonin receptors were 12 nM for the serotonin 5-HT_2A receptor, 120 nM for the serotonin 5-HT_2C receptor, 5,000 nM for the serotonin 5-HT_1B receptor, 7,100 nM for the serotonin 5-HT_1A receptor, and >10,000 nM for the serotonin 5-HT_1D receptor, whereas other serotonin receptors were not reported.^[3] Its capacity and potency in activating the serotonin receptors was also not reported.^[3]

The drug was developed by Richard Glennon and colleagues and was first described in 1990.^[3] At the time, it was described as the most 5-HT_2A receptor-selective tryptamine known to date.^[3]