4-HO-NPT

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4-HO-NPT
Clinical data
Other names4-Hydroxy-N-propyltryptamine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 3-[2-(propylamino)ethyl]-1H-indol-4-ol
PubChem CID
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  • CCCNCCC1=CNC2=C1C(=CC=C2)O
  • InChI=1S/C13H18N2O/c1-2-7-14-8-6-10-9-15-11-4-3-5-12(16)13(10)11/h3-5,9,14-16H,2,6-8H2,1H3
  • Key:MRUKLTXSCIPEBU-UHFFFAOYSA-N

4-HO-NPT, also known as 4-hydroxy-N-propyltryptamine, is a serotonin receptor modulator and putative psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to norpsilocin (4-HO-NMT).[1] It was not included by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects in humans are unknown.[2] The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[1] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, albeit with about 26-fold lower potency than psilocin (4-HO-DMT).[1] Unlike 4-HO-NPT, norpsilocin is notably inactive in this test.[1] In addition to its psychedelic-like effects, 4-HO-NPT produces hypolocomotion and hypothermia in rodents.[1] 4-HO-NPT was first described in the scientific literature by Alexander Sherwood and colleagues by 2024.[1]

See also

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References

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  1. ^ a b c d e f Sherwood AM, Burkhartzmeyer EK, Williamson SE, Baumann MH, Glatfelter GC (January 2024). "Psychedelic-like Activity of Norpsilocin Analogues". ACS Chemical Neuroscience. 15 (2): 315–327. doi:10.1021/acschemneuro.3c00610. PMC 10797613. PMID 38189238.
  2. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
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