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), 5-F-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

MSP-2020 is also a pyrrolidinylmethylindole, though its specific chemical structure has not been disclosed and is unclear.[6][7][8]

See also

References

  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.
  6. ^ "MSP 2020". AdisInsight. 14 January 2026. Retrieved 15 January 2026. MSP 2020 is an oral pyrrolidine-indole derivative psilocybin like high potency, short acting drug being developed by Otsuka America [...]
  7. ^ "3-pyrrolidine-indole derivatives as serotonergic psychedelic agents for the treatment of cns disorders". Google Patents. 4 February 2021. Retrieved 15 January 2026.
  8. ^ Mindset Pharma (5 October 2022). "Mindset Pharma Selects Lead Clinical Candidates From "Family 2" of its Next Generation Psychedelic Drug Portfolio". GlobeNewswire News Room. Retrieved 15 January 2026. MSP-2020 and MSP-2003, exhibiting a stronger and shorter acting psychedelic effect than psilocybin in preclinical testing, are selected for IND enabling studies [...] ("Mindset" or the "Company"), a drug discovery company developing novel, optimized, next-generation psychedelic and non-psychedelic medications to treat neuropsychiatric and neurological disorders with unmet medical needs, today announced that after extensive preclinical screening studies, a lead psychedelic drug clinical candidate, MSP-2020, and a second back-up drug candidate, MSP-2003, have been selected from its Family 2 program in collaboration with The McQuade Center for Strategic Research and Development, LLC (MSRD), a member of the global Otsuka family of pharmaceutical companies, to advance to IND enabling studies. [...] MSP-2020 and MSP-2003 are both novel and patentable compounds. They are covered under Mindset's United States Patent and Trademark Office (USPTO) patent number 17/387,864, titled "3-Pyrrolidine-Indole Derivatives as Serotonergic Psychedelic Agents for the Treatment of CNS Disorders." Mindset has received a notice of allowance from the USPTO for this application. [...] In side-by-side comparisons to psilocybin and psilocin, the two drug candidates elicit in vitro and behavioral responses consistent with a stronger and shorter acting psychedelic effect than psilocybin and a significantly reduced half-life. The drug candidates are CNS penetrant and exhibit high oral bioavailability in different species.



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