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Pyrrolidinylethylindole

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Class of chemical compounds

Pyrrolidinylethylindoles, or3-(2-pyrrolidinylethyl)indoles, also known aspyr-tryptamines orN,N-tetramethylenetryptamines, are a group ofcyclized tryptamines in which theamine has been replaced with orcyclized into apyrrolidinering. They can also be thought of asderivatives of thepsychedelic tryptamineN,N-diethyltryptamine (DET) in which theethyl groups attached to the amine have been connected together to form a ring. Examples of pyrrolidinylethylindoles includepyr-T,4-HO-pyr-T,5-MeO-pyr-T,4-F-5-MeO-pyr-T, andL-760790.

Pyrrolidinylethylindoles are known to act asserotonin receptor agonists, primarily of theserotonin5-HT1A receptor and to variably lesser extents of the serotonin5-HT2A receptor. In addition, they are known to bepsychoactive drugs and some havepsychedelic-like effects, although they are very different in their subjective effects compared to other psychedelic tryptamines.[1][2][3][4][5][6][7][8][9][10]

Chemical structures of selected pyrrolidinylethylindoles

See also

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References

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  1. ^Shulgin, Alexander;Shulgin, Ann (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.
  2. ^Shulgin AT (2003)."Basic Pharmacology and Effects". In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137.ISBN 978-0-12-433951-4. Retrieved1 February 2025.
  3. ^Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN 978-0-85608-011-1.OCLC 2176880.OL 4850660M.The cyclic analogue of DET, 3-(2-pyrrolidinoethyl)indole (4.13), was as active as the parent compound in behavioural tests in rodents, cats, and primates (Brimblecombe, 1967; Hunt and Brimblecombe, 1967; Brad Icy and Johnston, 1970). The compound was effective at doses down to 0·5 mg./kg. (s.c.) in disrupting the ability of monkeys to perform learned responses, but it is active only at levels which approach its lethal dose and it is unlikely to be tested in man. [...] Compounds of interest which have not been tested in man include [...] 5-methoxy-3-(2-pyrrolidinoethyl)indole, which is the most potent tryptamine so far revealed by the open field test, though its high toxicity will preclude tests in man (Brimblecombe, 1967; Hunt and Brimblecombe, 1967).
  4. ^Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics".Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43.doi:10.1007/7854_2017_475.ISBN 978-3-662-55878-2.PMID 28401524.Tethering the dialkyl groups into a heterocyclic ring gave mixed results; N-pyrrolidyl had an affinity similar to N,N-dimethyltryptamine (110 vs. 75 nM, respectively), but the affinity for the N-piperidyl was much lower, at 760 nM.
  5. ^McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes".Neuropharmacology.29 (3):193–198.doi:10.1016/0028-3908(90)90001-8.PMID 2139186.
  6. ^Sard H, Kumaran G, Morency C, Roth BL, Toth BA, He P, Shuster L (October 2005). "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist".Bioorganic & Medicinal Chemistry Letters.15 (20):4555–4559.doi:10.1016/j.bmcl.2005.06.104.PMID 16061378.
  7. ^Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024)."Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties".Molecular Psychiatry.29 (8):2346–2358.doi:10.1038/s41380-024-02506-8.PMC 11412900.PMID 38486047.
  8. ^Puigseslloses P, Islam MN, Ketsela G, Holy M, Niello M, Berzosa X, Camarasa J, Pubill D, Sitte H, Escubedo E, López-Arnau R, Nadal-Gratacós N (2023)."5-MeO-MET, 5-MeO-DET and 5-MeO-pyr-T strongly bind to 5-HT1A and 5-HT2A receptors and act as partial SERT substrates".Neuroscience Applied.2 103724.doi:10.1016/j.nsa.2023.103724.
  9. ^Laban U, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE (March 2001). "A novel fluorinated tryptamine with highly potent serotonin 5-HT1A receptor agonist properties".Bioorganic & Medicinal Chemistry Letters.11 (6):793–795.doi:10.1016/s0960-894x(01)00062-2.PMID 11277522.
  10. ^Warren AL, Lankri D, Cunningham MJ, Serrano IC, Parise LF, Kruegel AC, et al. (June 2024)."Structural pharmacology and therapeutic potential of 5-methoxytryptamines"(PDF).Nature.630 (8015):237–246.doi:10.1038/s41586-024-07403-2.PMC 11152992.PMID 38720072.
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
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Cyclized
Bioisosteres
Phenethylamines
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Ψ-PEA
MDxx
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25x-NB (NBOMes)
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Lysergamides
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Natural sources
5-HT1
5-HT1A
5-HT1B
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5-HT1F
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5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
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5-HT5A
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Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
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N-Acetyltryptamines
α-Alkyltryptamines
α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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