Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

N-Isopropyltryptamine

From Wikipedia, the free encyclopedia

Pharmaceutical compound
N-Isopropyltryptamine
Clinical data
Other namesNiPT; IPT; N-iP-T
Drug classSerotonin receptor agonist;Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • N-[2-(1H-indol-3-yl)ethyl]propan-2-amine
CAS Number
PubChemCID
ChemSpider
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • CC(C)NCCC1=CNC2=CC=CC=C21
  • InChI=1S/C13H18N2/c1-10(2)14-8-7-11-9-15-13-6-4-3-5-12(11)13/h3-6,9-10,14-15H,7-8H2,1-2H3
  • Key:QOCRVKNKLPEDCZ-UHFFFAOYSA-N

N-Isopropyltryptamine (NiPT) is aserotonin receptor agonist of thetryptamine family.[1][2]

Use and effects

[edit]

According toAlexander Shulgin, no active dose level of NiPT has yet been found in humans.[1]

Pharmacology

[edit]

Pharmacodynamics

[edit]

NiPT acts as apotentfull agonist of theserotonin5-HT2A receptor, whereas it is inactive as an agonist of the serotonin5-HT1A receptor.[2] The drug is also a weakserotonin reuptake inhibitor.[2]

Chemistry

[edit]

Analogues

[edit]

Analogues of NiPT includeN-methyltryptamine (NET),N-ethyltryptamine,N-sec-butyltryptamine (NsBT),N-tert-butyltryptamine (NtBT), anddiisopropyltryptamine (DiPT), among others.[1]

Derivatives

[edit]

Somederivatives of NiPT include4-HO-NiPT,5-HO-NiPT, and5-MeO-NiPT, among others.[3][4][5][6] 5-MeO-NiPT is likewise a serotonin receptor agonist.[7][5][2] It is a potentfull agonist or high-efficacypartial agonist of the serotonin 5-HT1A, 5-HT2A,5-HT2B, and5-HT2C receptors.[7][5][2] In contrast to5-MeO-NMT and5-MeO-NET, which are inactive in the test, 5-MeO-NiPT induces thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents, and hence may behallucinogenic in humans.[7][5] 4-HO-NiPT is also a serotonin receptor agonist and produces the head-twitch response in rodents as well.[6]

See also

[edit]

References

[edit]
  1. ^abcAlexander T. Shulgin,Ann Shulgin (1997).TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press.ISBN 978-0-9630096-9-2.OCLC 38503252. Retrieved30 January 2025.The homologue with only one isopropyl group on the nitrogen, N-isopropyltryptamine or NIPT IPT, has been made according to the same recipe, with the indol-3-yl N-isopropylglyoxalylamide (mp 199–200 °C from methanol) obtained in a 98% yield, and the amine hydrochloride (mp 245–246 °C from benzene/methanol) obtained in a 60% yield. The free base distilled at 130–140 °C at 0.1 mm/Hg to give a fraction that spontaneously crystallized to a very hard solid. MS (in m/z): C4H10N+ 72 (100%); indolemethylene+ 131 (60%), 130 (32%); parent ion 202 (3%). No active level has yet been found in man, to my knowledge.
  2. ^abcdeBlough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014)."Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes".Psychopharmacology.231 (21). Berlin:4135–4144.doi:10.1007/s00213-014-3557-7.PMC 4194234.PMID 24800892.
  3. ^Araújo AM, Carvalho F, Bastos ML, Guedes de Pinho P, Carvalho M (August 2015)."The hallucinogenic world of tryptamines: an updated review"(PDF).Archives of Toxicology.89 (8):1151–1173.Bibcode:2015ArTox..89.1151A.doi:10.1007/s00204-015-1513-x.PMID 25877327.
  4. ^Laban U, Naeem M, Chadeayne AR, Golen JA, Manke DR (March 2023)."Synthesis and structure of 4-hy-droxy-N-iso-propyl-tryptamine (4-HO-NiPT) and its precursors".Acta Crystallographica Section E: Crystallographic Communications.79 (Pt 4):280–286.Bibcode:2023AcCrE..79..280L.doi:10.1107/S2056989023002098.PMC 10088304.PMID 37057027.
  5. ^abcdPuigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, et al. (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.
  6. ^abSherwood 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.
  7. ^abcGlatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, et al. (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice".ACS Chemical Neuroscience.15 (24):4458–4477.doi:10.1021/acschemneuro.4c00513.PMID 39636099.

External links

[edit]
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=N-Isopropyltryptamine&oldid=1323687857"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp