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Pyrrolidinylmethylindole

Pyrrolidinylmethylindoles, or 3-(pyrrolidin-2-ylmethyl)-1H-indoles, also known as α,N-trimethylenetryptamines, are a group of cyclized tryptamines in which the amine has been cyclized with the α position of the ethyl side chain via a propyl group to form a pyrrolidine ring. They include the psychedelic and related compounds MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, and 5-MeO-MPMI and the triptans and related compounds eletriptan and CP-135807. Pyrrolidinylmethylindoles are known to act as serotonin receptor agonists, including of the serotonin 5-HT1 and/or 5-HT2 receptors.[1][2][3][4][5]

Chemical structures of selected pyrrolidinylmethylindoles


See also

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References

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  1. ^ Macor JE, Blake J, Fox CB, Johnson C, Koe BK, Lebel LA, Morrone JM, Ryan K, Schmidt AW, Schulz DW, et al. (1992). "Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin". Journal of Medicinal Chemistry. 35 (23): 4503–5. doi:10.1021/jm00101a032. PMID 1447752.
  2. ^ Gerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE (1999). "Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain". Journal of Medicinal Chemistry. 42 (20): 4257–4263. CiteSeerX 10.1.1.690.4941. doi:10.1021/jm990325u. PMID 10514296.
  3. ^ WO 2022/256554, Wallach J, Dybek M, "Fluorinated Tryptamine Compounds, Analogues Thereof, and Methods Using Same", published 8 December 2022, assigned to University of the Sciences in Philadelphia.  Retrieved 2025-05-14
  4. ^ Mansbach RS, Rovetti CC, Macor JE (December 1996). "CP-135,807, a selective 5-HT1D agonist: effects in drug discrimination and punishment procedures in the pigeon". Psychopharmacology (Berl). 128 (3): 313–319. doi:10.1007/s002130050139. PMID 8972551.
  5. ^ McCormack PL, Keating GM (2006). "Eletriptan: a review of its use in the acute treatment of migraine". Drugs. 66 (8): 1129–1149. doi:10.2165/00003495-200666080-00010. PMID 16789799.



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