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5-MeO-PiPT

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Chemical compound

Pharmaceutical compound

5-MeO-PiPT
Identifiers

IUPAC name N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-1-amine
CAS Number	2945111-53-3^Y
PubChemCID	166468735
Chemical and physical data
Formula	C₁₇H₂₆N₂O
Molar mass	274.408 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)N(CCC)CCc1c[NH]c2ccc(cc21)OC
InChI InChI=1S/C17H26N2O/c1-5-9-19(13(2)3)10-8-14-12-18-17-7-6-15(20-4)11-16(14)17/h6-7,11-13,18H,5,8-10H2,1-4H3 Key:KLRSMSBDLVDLKK-UHFFFAOYSA-N

5-Methoxy-N-propyl-N-isopropyltryptamine (5-MeO-PiPT) is asubstituted tryptamine derivative which is claimed to havepsychedelic effects. It acts as a 5-HT_1A and 5-HT_2A receptor agonist,^[1] with an EC₅₀ of 13.8 nM and an efficacy of 89% (vs 5-HT),^[2] and has been sold as adesigner drug, first being identified in 2021 inBritish Columbia,Canada.^[3]

References

[edit]

^Warren AL, Lankri D, Cunningham MJ, Serrano IC, Parise LF, Kruegel AC, Duggan P, Zilberg G, Capper MJ, Havel V, Russo SJ, Sames D, Wacker D (June 2024)."Structural pharmacology and therapeutic potential of 5-methoxytryptamines".Nature.630 (8015):237–246.doi:10.1038/s41586-024-07403-2.PMC 11152992.PMID 38720072.
^Banister S, Jorgensen W, Jinlong T. Compounds. Patent WO 2023/115167
^Knill A, Tobias S, Matthews J, Ti L (June 2022).A Report on British Columbia's Unregulated Drug Supply. Drug checking trends across British Columbia, January to December 2021(PDF).British Columbia Centre on Substance Use (Report).

v t e Tryptamines
Tryptamines	1-Methyl-T 1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4,5-DHT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-DPT 4-AcO-EPT 4-AcO-MALT 4-AcO-MET 4-AcO-MiPT 4-AcO-NMT 4-AcO-TMT 4-F-5-MeO-pyr-T 4-F-5-MeO-DMT 4-Fluoro-DMT 4-Fluoro-T 4-HO-5-MeO-T 4-HO-DALT 4-HO-DBT 4-HO-DET 4-HO-DPT 4-HO-DSBT 4-HO-EiBT 4-HO-EPT 4-HO-MALT 4-HO-MET 4-HO-McPT 4-HO-McPeT 4-HO-MiPT 4-HO-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NiPT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-HO-TMT 4-HT 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-HO-DiPT 5-HO-NiPT 5-HTP (oxitriptan) 5-Me-MiPT 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT 5-MeO-PiPT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine) 5-MeO-T-NBOMe 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-MT-NB3OMe 5-NOT 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-MeO-DMT 6-MeO-T 6-Methyl-T 6,7-DHT 7-Chloro-T 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Alpertine Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L-tryptophan) Bretisilocin (5-fluoro-MET) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Bufoviridine (5-SO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Isamide Lespedamine MBT MET Milipertine Miprocin (4-HO-MiPT) MiPT MPT MS-245 MSBT N-Feruloylserotonin (moschamine) NBoc-DMT NET/NETP NiPT NMT Norbaeocystin (4-PO-T) NTBT O-4310 O-Pivalylbufotenine Oxypertine PiPT Psilacetin (O-acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Psilomethoxin (4-HO-5-MeO-DMT) Pyr-T RS134-49 10,11-Secoergoline (α,N-Pip-T) Serotonin (5-HT) Solypertine ST-1936 Tryptamine (T) Tryptophan Yuremamine Z2876442907
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301
α-Alkyltryptamines	1-Pr-5-MeO-AMT 2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Allyloxy-AMT 5-Chloro-αET 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-α,N,N-TMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N-DMT (N-methyl-αMT) α,N,N-TMT α,N,O-TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT BW-723C86 CP-135807 IPAP (α,N-DPT) MPMI Soclenicant (BNC-210)
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Bay R 1531 Ciclindole Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD) Flucindole Harmala alkaloids andβ-carbolines (e.g.,6-MeO-THH,9-Me-BC,β-carboline (norharman),harmaline,harmalol,harmane,harmine,pinoline,tetrahydroharmine,tryptoline) Iboga alkaloids and related (e.g.,DM-506 (ibogaminalog),ibogaine,ibogamine,noribogaine,tabernanthalog,tabernanthine) LY-266,097 Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans (e.g.,yohimbine,rauwolscine,spegatrine,corynanthine,ajmalicine,reserpine,deserpidine,rescinnamine)
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT isoDMT Isotryptamine (isoT) PNU-181731 Ro60-0175 Zalsupindole (DLX-001, AAZ-A-154)
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT AL-34662 AL-38022A Benzofurans (e.g.,3-APB,5-MeO-DiBF,BPAP,dimemebfe,mebfap) BRL-54443 CP-94253 EMD-386088 I-32 IAL Latrepirdine LY-367265 Masupirdine Non-tryptaminetriptans (e.g.,avitriptan,LY-334370,naratriptan) Pirlindole (R)-69 (3IQ) Ro60-0213 RU-24,969 Sertindole SN-22 Tepirindole Tetrindole VER-3323 VU6067416 YM-348

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