From Wikipedia, the free encyclopedia
Tetrahydropyridinylpyrrolopyridines are a group of pyrrolopyridine–tetrahydropyridine derivatives related to the tryptamines. They are not tryptamines themselves, as they feature a pyrrolopyridine instead of indole ring system. The compounds include (R)-69, (R)-70, and CP-94253. They are known to act as serotonin receptor agonists, including of the serotonin 5-HT1 and/or 5-HT2 receptors.[1][2] Some tetrahydropyridinylpyrrolopyridines, such as (R)-69 and (R)-70, were discovered by Bryan L. Roth and colleagues via ultra-large-scale docking.[2]
Chemical structures of selected tetrahydropyridinylpyrrolopyridines
- ^ Koe, B. Kenneth; Nielsen, Jann A.; Macor, John E.; Heym, James (1992). "Biochemical and behavioral studies of the 5-HT 1B receptor agonist, CP-94,253". Drug Development Research. 26 (3): 241–250. doi:10.1002/ddr.430260305. ISSN 0272-4391. Retrieved 30 July 2025.
- ^ a b Kaplan AL, Confair DN, Kim K, Barros-Álvarez X, Rodriguiz RM, Yang Y, Kweon OS, Che T, McCorvy JD, Kamber DN, Phelan JP, Martins LC, Pogorelov VM, DiBerto JF, Slocum ST, Huang XP, Kumar JM, Robertson MJ, Panova O, Seven AB, Wetsel AQ, Wetsel WC, Irwin JJ, Skiniotis G, Shoichet BK, Roth BL, Ellman JA (October 2022). "Bespoke library docking for 5-HT2A receptor agonists with antidepressant activity". Nature. 610 (7932): 582–591. doi:10.1038/s41586-022-05258-z. PMC 9996387. PMID 36171289.
|
|---|
| Tryptamines |
- 1-Methyl-DMT (1,N,N-TMT, 1-TMT)
- 1-Methyl-T
- 2-HO-NMT
- 2-Methyl-DET
- 2-Methyl-DiPT
- 2-Methyl-iPALT (ASR-3002)
- 2,N,N-TMT (2-methyl-DMT)
- 3-IAAR
- 4-Fluoro-DMT
- 4-Fluoro-T
- 4-Methyl-DMT
- 5-Bromo-DMT
- 5-Bromo-T
- 5-Chloro-DMT
- 5-Chloro-T
- 5-CT
- 5-Ethyl-DMT
- 5-Fluoro-DET
- 5-Fluoro-DMT
- 5-Fluoro-EPT
- 5-Fluoro-T
- 5-Me-MiPT
- 5-MeS-DMT
- 5-Methyl-DMT
- 5-Methyl-T
- 5-Nitro-T (Nitro-I)
- 6-Fluoro-DET
- 6-Fluoro-DMT
- 6-Fluoro-T
- 6-HO-DET
- 6-HO-DMT
- 6-HO-T (6-HT)
- 6-MeO-DMT
- 6-MeO-T
- 6-Methyl-DMT
- 6-Methyl-T
- 6,7-DHT
- 7-Chloro-T
- 7-HO-DMT
- 7-HO-T (7-HT)
- 7-MeO-DMT
- 7-MeO-T
- 7-Methyl-DMT
- 7-Methyl-T
- 7-Hydroxytryptophan
- Acetryptine (5-AT)
- Almotriptan
- Benzotript (4-CB-Trp)
- BGE
- Bretisilocin (5-fluoro-MET; GM-2505)
- Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT)
- DALT
- DAT
- DBT
- Desformylflustrabromine
- DET (T-9)
- DHT
- DiPT
- DMT
- DPT
- E-6801
- E-6837
- EB-003
- EiPT
- EPT
- FGIN-127
- FGIN-143
- Idalopirdine
- iPALT (ALiPT; ASR-3003)
- Lespedamine (1-MeO-DMT)
- L-694247
- MBT
- McPT
- MET
- MiPT
- MPT
- MsBT
- N-Benzyltryptamine (T-NB, NB-T)
- N-DEAOP-NET
- N-DEAOP-NMT
- NAT
- NBoc-DMT (NB-DMT)
- NET/NETP
- NHT
- NiPT
- NMT
- NsBT
- NtBT
- PALT (ASR-3004)
- PiPT
- Rizatriptan
- ST-1936 (2-Me-5-Cl-DMT)
- Sumatriptan
- TCS-1205
- Tryptamine (T; indolylethylamine)
- Tryptophan (Trp)
- WAY-181187
- Yuremamine
- Z2876442907
- ZCZ-011
- Zolmitriptan
|
|---|
4-Hydroxytryptamines and esters/ethers | |
|---|
5-Hydroxy- and 5-methoxytryptamines |
- 2-Methyl-5-HT
- 2-Methyl-5-MeO-DALT
- 4-HO-5-MeO-T
- 4-F-5-MeO-DMT
- 4,5-DHP-DMT
- 4,5-DHT
- 4,5-MDO-DMT
- 4,5-MDO-DiPT
- 5-BT
- 5-Ethoxy-DMT
- 5-HO-DET
- 5-HO-DiPT
- 5-HO-DPT
- 5-HO-MET
- 5-HO-NiPT
- 5-HTP (oxitriptan)
- 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 (N,N,O-TMS; O-methylbufotenine)
- 5-MeO-DPT
- 5-MeO-EiPT
- 5-MeO-EPT
- 5-MeO-MALT
- 5-MeO-MBT
- 5-MeO-MET
- 5-MeO-MiPT
- 5-MeO-MsBT
- 5-MeO-NET
- 5-MeO-NiPT
- 5-MeO-NMT (O,N-DMS)
- 5-MeO-NsBT
- 5-MeO-PiPT
- 5-MeO-NBpBrT
- 5-MeO-T (5-MT; mexamine; O-methylserotonin)
- 5-MeO-T-NBOMe
- 5-MeO-T-NB3OMe
- 5-MTP (cytoguardin)
- 5-NOT
- 5-PhO-T (OVT2)
- 5,6-DHT
- 5,6-MDO-DiPT
- 5,6-MDO-DMT
- 5,6-MDO-MiPT
- 5,6-MeO-MiPT
- 5,7-DHT
- Arachidonoyl serotonin
- ASR-3001 (5-MeO-iPALT)
- BAB
- Benanserin (BAS; SQ-4788)
- BGC20-761
- Bufotenidine (5-HTQ; N,N,N-TMS)
- Bufotenin (5-HO-DMT; N,N-DMS; mappine)
- Bufoviridine (5-SO-DMT)
- CP-132,484
- Cqd 280
- Cqd 285
- Cqdd 280
- Donitriptan
- EMDT (2-Et-5-MeO-DMT)
- HIOC
- Indorenate (TR-3369)
- IS-159
- Isamide (N-CA-5-MT)
- L-741604
- MS-245
- N-DEAOP-5-MeO-NET
- N-DEAOP-5-MeO-NMT
- N-Feruloylserotonin (moschamine)
- NB-5-MeO-DALT
- NB-5-MeO-MiPT
- Norbufotenin (5-HO-NMT; NMS)
- O-Acetylbufotenine (5-AcO-DMT)
- O-Pivalylbufotenine (5-t-BuCO-DMT)
- Psilomethoxin (4-HO-5-MeO-DMT)
- Psilomethoxybin (4-PO-5-MeO-DMT)
- Serotonin (5-HT)
|
|---|
| N-Acetyltryptamines | |
|---|
| α-Alkyltryptamines |
- 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT
- 5-Allyloxy-AMT
- 5-Ethoxy-αMT
- 5-iPrO-αMT
- 5-MeO-αET
- 5-MeO-αMT (α,O-DMS; Alpha-O)
- α-Methyl-5-HTP
- α-Methylmelatonin
- α-Methylserotonin (5-HO-αMT; α-Me-5-HT)
- α,N,O-TMS (5-MeO-α,N-DMT)
- α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
- AL-37350A (4,5-DHP-αMT)
- BW-723C86
|
|---|
| α-Ketotryptamines | |
|---|
| Cyclized tryptamines |
- 5-MeO-IsoqT
- Barettin
- BML-190 (indomethacin morpholinylamide)
- Cyclic 3-OHM
- Ergolines and lysergamides (e.g., LSD)
- Harmala alkaloids and β-carbolines (e.g., 5-methoxyharmalan, 6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline)
- Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine, tabernanthine)
- Ibogalogs (e.g., catharanthalog, fluorogainalog, ibogainalog, ibogaminalog (DM-506), LS-22925, noribogainalog, noribogaminalog, PHA-57378, PNU-22394, tabernanthalog)
- Imidazolylindoles (e.g., AGH-107, AGH-192, AH-494)
- Metralindole
- Morpholinylethylindoles (e.g., mor-T, 5-MeO-mor-T)
- Partial ergolines and lysergamides (e.g., NDTDI, RU-27849, RU-28251, RU-28306, FHATHBIN, LY-178210, Bay R 1531 (LY-197206), LY-293284, 10,11-seco-LSD, 10,11-secoergoline (α,N-Pip-T), CT-5252)
- Pertines (e.g., alpertine, milipertine, oxypertine, solypertine)
- Piperidinylethylindoles (e.g., pip-T, 5-MeO-pip-T, indolylethylfentanyl)
- Pyrrolidinylethylindoles (e.g., pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, L-760790)
- Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-122288, CP-135807, eletriptan, MSP-2020)
- Tetrahydrocarbazolamines (e.g., ciclindole, flucindole, frovatriptan, LY-344864, ramatroban)
- Tetrahydropyridinylindoles (e.g., RS134-49, RU-28253, NEtPhOH-THPI)
- Tetrahydropyrroloquinolines (e.g., bufothionine, O-methylnordehydrobufotenine, dehydrobufotenine)
- Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
|
|---|
| Isotryptamines | |
|---|
| Related compounds |
- 2-Azapsilocin
- 2,3-Dihydro-L-tryptophan
- 2,3-Dihydrotryptamine
- 2,3-Dihydro-DMT
- 2,3-Dihydro-NMT
- 2,3-Dihydro-DET
- 4-Aza-5-MeO-DPT
- 5-Aza-4-MeO-DiPT
- 5-HIAA
- 5-HIAL
- 5-HITCA
- 5-MIAL
- 7-Aza-5-MeO-DiPT
- α-Carboline
- γ-Carbolines (pyridoindoles) (e.g., γ-carboline, alosetron, gevotroline, latrepirdine, lurosetron, mebhydrolin, tiflucarbine)
- Amedalin
- Benzindopyrine
- Benzofurans (e.g., 3-APB (1-oxa-AMT), 5-MeO-DiBF (1-oxa-5-MeO-DiPT), BPAP, 3-F-BPAP, dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT), MiPBF (1-oxa-MiPT), oxa-noribogaine)
- Benzothiophenes (e.g., S-DMT (1-thia-DMT), 3-APBT (1-thia-AMT))
- Carmoxirole
- CT-4436
- Daledalin
- Gramine
- Histamine
- Homotryptamines (e.g., HT, DMHT)
- I-32
- IAL
- IN-399
- Indalpine
- Indazolethylamines (e.g., AL-34662, AL-38022A, O-methyl-AL-34662, VU6067416, YM-348)
- Indenylethylamines (e.g., C-DMT (1-carba-DMT))
- Indolizinylethylamines (e.g., TACT908 (2ZEDMA), 1ZP2MA, 1Z2MAP1O)
- Indolylaminopropanes (e.g., 1-API, 2-API, 4-API, 5-API (5-IT; PAL-571), 6-API (6-IT), 7-API)
- Iprindole
- Masupirdine
- Medmain
- Molindone
- Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan)
- Ondansetron
- Oxazinopyridoindoles (e.g., IHCH-8134)
- Phenethylamines (e.g., phenethylamine, amphetamine)
- Piperidinylbenzimidazolines (e.g., benperidol, timiperone)
- Piperazinylbenzisothiazoles (e.g., lurasidone, perospirone, tiospirone, ziprasidone)
- Piperidinylbenzisoxazoles (e.g., iloperidone, milsaperidone, ocaperidone, paliperidone, risperidone)
- Piperidinylindoles (e.g., BRL-54443, LY-334370, naratriptan, sertindole, SN-22)
- Pirlindole
- Pyridinylbenzimidazoles (e.g., droperidol)
- Pyridinylindoles (e.g., tepirindole)
- Pyridopyrroloquinoxalines (e.g., IHCH-7113, IHCH-7079, IHCH-7086, lumateperone, deulumateperone, ITI-1549)
- Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA), 3-pyrrolylethylamine (3-NEA), 3-pyrrolylpropylamine)
- Pyrrolopyridinylethylamines (e.g., WAY-208466)
- Quinolinylethylamines (e.g., mefloquine)
- Ro60-0213
- Selisistat
- Tetrahydropyridinylindoles (e.g., EMD-386088, LY-367265, RU-24,969)
- Tetrahydropyridinylpyrrolopyridines (e.g., (R)-69 (3IQ), (R)-70, CP-93129, CP-94253)
- Tetrindole
- Tipindole
- Zilpaterol (RU-42173)
|
|---|
|