5-Fluoro-EPT

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5-Fluoro-EPT
5-Fluoro-EPT.svg
Identifiers
  • N-ethyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]propan-1-amine
PubChem CID
Chemical and physical data
Formula C15H21FN2
Molar mass 248.345 g·mol−1
3D model (JSmol)
  • CCCN(CC)CCC1=CNC2=C1C=C(C=C2)F
  • InChI=1S/C15H21FN2/c1-3-8-18(4-2)9-7-12-11-17-15-6-5-13(16)10-14(12)15/h5-6,10-11,17H,3-4,7-9H2,1-2H3
  • Key:QONMHCQBCANXJS-UHFFFAOYSA-N

5-Fluoro-EPT (5F-EPT, 5-fluoro-N-ethyl-N-propyltryptamine) is a psychedelic tryptamine derivative related to drugs such as EPT and 5-MeO-EPT. It acts as a potent full agonist at the 5-HT2A receptor with an EC50 of 5.54 nM and an efficacy of 104% (compared to serotonin). It produces a head-twitch response in animal studies, and is claimed to have antidepressant activity. [1]

See also

Related Research Articles

5-MeO-DPT Chemical compound

5-MeO-DPT, is a psychedelic and entheogenic designer drug.

5-Fluoro-AMT Chemical compound

5-Fluoro-α-methyltryptamine, also known as PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent, a 5-HT2A receptor agonist, and a potent and specific MAO-A inhibitor. It produces a strong head-twitch response in mice, and this effect is known to correlate with psychedelic effects in humans, which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.

5-Fluoro-DMT Chemical compound

5-Fluoro-N,N-dimethyltryptamine is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT. Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist, while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT1A than 5-HT2A.

6-Fluoro-DMT Chemical compound

6-Fluoro-N,N-dimethyltryptamine (6-Fluoro-DMT) is a synthetic drug of the tryptamine chemical class.

4-Fluoro-5-methoxy-DMT

4-Fluoro-5-Methoxy-N,N-dimethyltryptamine (4-F-5-MeO-DMT) was first described by David E. Nichols team in 2000. It is a potent 5-HT1A agonist. Substitution with the 4-fluorine markedly increased 5-HT1A selectivity over 5-HT2A/2C receptors with potency greater than that of the 5-HT1A agonist 8-OH-DPAT.

5-Ethoxy-DMT Chemical compound

5-Ethoxy-DMT is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology.

O-4310 Chemical compound

O-4310 (1-isopropyl-6-fluoro-psilocin) is a tryptamine derivative developed by Organix Inc which acts as a serotonin receptor agonist. It is claimed to have an EC50 of 5nM at 5-HT2A with 89% efficacy vs 5-HT, and 100x selectivity over 5-HT2C, while being apparently inactive at the 5-HT2B antitarget.

6-Fluoro-AMT Chemical compound

6-Fluoro-α-methyltryptamine is a tryptamine derivative related to compounds such as alpha-methyltryptamine and 5-MeO-AMT, which has been sold as a designer drug. Animal tests showed it to be somewhat less active than AMT or 5-fluoro-AMT, but it was nevertheless allegedly manufactured and sold from the laboratory operated by Leonard Pickard and Gordon Todd Skinner, who described 6-fluoro-AMT as "a beast".

5-Chloro-αMT Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

Ethylpropyltryptamine Chemical compound

Ethylpropyltryptamine is a rarely encountered psychedelic substance from the tryptamine class, which makes it structurally related to DMT, MET, DET, and DPT.

4-HO-EPT Chemical compound

4-HO-EPT (4-hydroxy-N-ethyl-N-propyltryptamine) is a rarely encountered chemical compound of the tryptamine class, which makes it structurally related to psilocin (4-HO-DMT).

4-HO-McPT Chemical compound

4-HO-McPT (4-hydroxy-N-methyl-N-cyclopropyltryptamine) is a psychedelic tryptamine derivative. It has serotonergic effects, and has reportedly been sold as a designer drug since around 2016, but was not definitively identified by forensic laboratories until 2018. It is illegal in Finland.

5-MeO-EPT

5-MeO-EPT is a psychedelic tryptamine derivative which has been sold as a designer drug.

5-MeO-MET

5-MeO-MET (5-Methoxy-N-methyl-N-ethyltryptamine) is a relatively rare designer drug from the substituted tryptamine family, related to compounds such as N-methyl-N-ethyltryptamine and 5-MeO-DMT. It was first synthesised in the 1960s and was studied to a limited extent, but was first identified on the illicit market in June 2012 in Sweden. It was made illegal in Norway in 2013, and is controlled under analogue provisions in numerous other jurisdictions.

5-MeO-DBT Chemical compound

5-MeO-DBT is a rare substituted tryptamine derivative, which is thought to be a psychoactive substance and was identified in a designer drug sample by a forensic laboratory in Slovenia in March 2021, although only analytical studies have been conducted and no pharmacological data is available. It is nevertheless controlled under drug analogue legislation in a number of jurisdictions.

5-Fluoro-AET Chemical compound

5-Fluoro-α-ethyltryptamine (5-F-AET) is a tryptamine derivative which acts as a serotonin–dopamine releasing agent and agonist of the 5-HT2A receptor.

5-Chloro-DMT Chemical compound

5-Chloro-N,N-dimethyltryptamine (5-chloro-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-fluoro-DMT. It acts as a serotonin receptor agonist and has primarily sedative effects in animal studies. It has been sold as a designer drug.

5-Fluoro-MET Chemical compound

5-Fluoro-MET (5F-MET, 5-fluoro-N-methyl-N-ethyltryptamine) is a psychedelic tryptamine derivative related to drugs such as 5-Fluoro-DMT and N-Methyl-N-ethyltryptamine (MET). It acts as an agonist at the 5-HT2A receptor with an EC50 of 20.6 nM and produces a head-twitch response in animal studies. Ring fluorination in this case increases efficacy at 5-HT2A, with 5F-MET having an efficacy of 87.6% vs 5-HT, vs 36.2% for the partial agonist MET. It is claimed to have antidepressant activity.

5-Fluoro-DET Chemical compound

5-Fluoro-DET is a tryptamine derivative related to drugs such as DET and 5-MeO-DET. It acts as an inhibitor of the enzyme myeloperoxidase, and is also thought to be an agonist at the 5-HT2A receptor.

6-Fluoro-DET Chemical compound

6-Fluoro-DET is a substituted tryptamine derivative related to drugs such as DET and 5-fluoro-DET. It acts as a partial agonist at the 5-HT2A receptor, but while it produces similar physiological effects to psychedelic drugs, it does not appear to produce psychedelic effects itself even at high doses. For this reason it saw some use as an active placebo in early clinical trials of psychedelic drugs but was regarded as having little use otherwise, though more recent research into compounds such as AL-34662 and AAZ-A-154 has shown that these kind of non-psychedelic 5-HT2A agonists can have various useful applications.

References

  1. WO 2021/168082,Kruegel AC, Sporn J,"Specific Tryptamines for use in the Treatment of Mood Disorders.",published 26 August 2021, assigned to Gilgamesh Pharmaceuticals, Inc..