`Foxtrot' fumarate: a water-soluble salt of <i>N</i>,<i>N</i>-diallyl-5-methoxytryptamine (5-MeO-DALT)

Pham, Duyen N. K.; Sammeta, Vamshikrishna Reddy; Chadeayne, Andrew R.; Golen, James A.; Manke, David R.

doi:10.1107/s2056989021002838

Cited by 4 publications

(1 citation statement)

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“…norpsilocin (Chadeayne et al, 2020b), 4-acetoxy-N,N-diallyltryptamine (Pham et al, 2021a), 5-methoxy-N,N-diallyltryptamine (Pham, Sammeta et al, 2021), 5-methoxy-N,N-din-propyltryptamine (Pham et al, 2021c), 4-hydroxy-N-methyl-N-isopropyltryptamine (Chadeayne et al, 2020a), 5-methoxy-2-methyl-N,N-dimethyltryptamine (Pham et al, 2021b), 4-hydroxy-N,N-di-n-propyltryptamine (Chadeayne, Pham et al, 2019), and 4-acetoxy-N,N-dimethyltryptamine (Chadeayne et al, 2019a).…”

Section: Figurementioning

confidence: 99%

N-Cyclohexyltryptamine: freebase, bromide and fumarate

Naeem,

Le,

Bauer

et al. 2023

Acta Cryst E

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The solid-state structures of N-cyclohexyltryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine}, C16H22N2, and two of its salts, N-cyclohexyltryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium bromide}, C16H23N2 +·Br−, and N-cyclohexyltryptammonium fumarate (III) (systematic name: bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium} (2E)-but-2-enedioate), 2C16H23N2 +·C4H2O4 2−, were determined by single-crystal X-ray diffraction. The freebase compound forms infinite chains along [010] through N—H...N hydrogen bonds. The bromide salt is held together by N—H...Br interactions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N—H...O hydrogen bonds.

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Section: Figurementioning

confidence: 99%

N-Cyclohexyltryptamine: freebase, bromide and fumarate

Naeem,

Le,

Bauer

et al. 2023

Acta Cryst E

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Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice

Glatfelter,

Clark,

Cavalco

et al. 2024

ACS Chem. Neurosci.

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5-methoxy-N,N-dimethyltrytpamine (5-MeO-DMT) analogs are used as recreational drugs, but they are also being developed as potential medicines, warranting further investigation into their pharmacology. Here, we investigated the neuropharmacology of 5-MeO-DMT and several of its N-alkyl, Nallyl, and 2-methyl analogs, with three major aims: 1) to determine in vitro receptor profiles for the compounds, 2) to characterize in vitro functional activities at serotonin (5-HT) 2A receptors (5-HT 2A ) and 1A receptors (5-HT 1A ), and 3) to examine the influence of 5-HT 1A on 5-HT 2A -mediated psychedelic-like effects in the mouse head twitch response (HTR) model. In vitro receptor binding and functional assays showed that all 5-MeO-DMT analogs bind with high affinity and activate multiple targets (e.g., 5-HT receptor subtypes, alpha adrenergic receptors), including potent effects at 5-HT 2A and 5-HT 1A . In C57Bl/6J mice, subcutaneous injection of the analogs induced HTRs with varying potencies (ED 50 range = 0.2−1.8 mg/kg) and maximal effects (E max range = 20− 60 HTRs/30 min), while inducing hypothermia and hypolocomotion at higher doses (ED 50 range = 3.2−20.6 mg/kg). 5-HT 2A antagonist pretreatment blocked drug-induced HTRs, whereas 5-HT 1A antagonist pretreatment enhanced HTRs. In general, N,Ndialkyl and N-isopropyl derivatives displayed HTR activity, while the N-methyl, N-ethyl, and 2-methyl analogs did not. Importantly, blockade of 5-HT 1A unmasked latent HTR activity for the N-ethyl analog and markedly increased maximal responses for other HTRactive compounds (40−90 HTRs/30 min), supporting the notion that 5-HT 1A agonist activity can dampen 5-HT 2A -mediated HTRs. Suppression of 5-HT 2A -mediated HTRs by 5-HT 1A only occurred after high 5-MeO-DMT doses, suggesting involvement of other receptors in modulating psychedelic-like effects. Overall, our findings provide key information about the receptor target profiles for 5-MeO-DMT analogs, the structure−activity relationships for inducing psychedelic-like effects, and the critical role of 5-HT 1A agonism in modulating acute psychoactive effects of 5-HT 2A agonists.

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