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1-Propyl-5-MeO-AMT

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Pharmaceutical compound
1-Propyl-5-MeO-AMT
Clinical data
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;Serotonin5-HT2A receptormodulator
Identifiers
  • 1-(5-methoxy-1-propylindol-3-yl)propan-2-amine
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • CCCN1C=C(C2=C1C=CC(=C2)OC)CC(C)N
  • 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

1-Propyl-5-MeO-AMT, also known as1-propyl-5-methoxy-α-methyltryptamine, is aserotonin receptor modulator of thetryptamine,α-alkyltryptamine, and5-methoxytryptamine families.[1][2][3] It is the 1-propylderivative of5-methoxy-α-methyltryptamine (5-MeO-AMT).[3]

Whereas most tryptamines are highlynon-selective in terms of binding toserotonin receptors, 1-propyl-5-MeO-AMT showsselectivity for theserotonin5-HT2A receptor.[1][2][3] Itsaffinities (Ki) for serotonin receptors were 12 nM for the serotonin 5-HT2A receptor, 120 nM for the serotonin5-HT2C receptor, 5,000 nM for the serotonin5-HT1B receptor, 7,100 nM for the serotonin5-HT1A receptor, and >10,000 nM for the serotonin5-HT1D receptor, whereas other serotonin receptors were not reported.[3] Its capacity andpotency in activating the serotonin receptors was also not reported.[3]

The drug was developed byRichard Glennon and colleagues and was first described in 1990.[3] At the time, it was described as the most 5-HT2A receptor-selective tryptamine known to date.[3]

See also

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References

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  1. ^abAraújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review".Archives of Toxicology.89 (8):1151–1173.Bibcode:2015ArTox..89.1151A.doi:10.1007/s00204-015-1513-x.PMID 25877327.Like phenylalkylamines, the tryptamine hallucinogens such as LSD, psilocin, DMT or 5-MeO-DMT act as 5-HT2 receptor agonists, but they are much less selective, binding to a variety of 5-HT1 and 5-HT2 receptor subtypes (including 5-HT1A, 5-HT1B, 5-HT1C, 5-HT2A and 5-HT2C receptors) with different affinities (Blair et al. 2000; Fantegrossi et al. 2006, 2008a; McKenna et al. 1990; Peden et al. 1981; Strassman et al. 1996; Winter et al. 2000). For example, N1-n-propyl-5-methoxyα-methyltryptamine binds preferentially at 5-HT2 receptors (Glennon et al. 1990), while 5-MeO-DIPT has a considerably increased affinity for 5-HT1A receptors, although it also has affinity for 5-HT2A and 5-HT2C receptors (Fantegrossi et al. 2006).
  2. ^abVangveravong S (1994)."Synthesis of trans-2-(indol-3-yl)cyclopropylamines: Rigid tryptamine analogues".ProQuest.ProQuest 304131663. Retrieved22 March 2025.For example, 1-n-propyl-5-methoxy-α-methyltryptamine binds with significant affinity and selectivity at the 5-HT2 receptor relative to other 5-HT receptors.76 [...] 76. Glennon. R. A.; Chaurasia, Titeler, M. Binding of Indolylalkylamines at 5-HT Serotonin Receptors: Examination of a Hydrophobic Binding Region. J. Med. Chen 1990, 33, 2777-2784.
  3. ^abcdefgGlennon RA, Chaurasia C, Titeler M (October 1990). "Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region".Journal of Medicinal Chemistry.33 (10):2777–2784.doi:10.1021/jm00172a016.PMID 2213830.Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-α-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki > 10000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

External links

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5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
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Tryptamines
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andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
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