5-Fluoro-EPT

Chemical compound

Pharmaceutical compound

5-Fluoro-EPT
Identifiers

IUPAC name N-ethyl-N-[2-(5-fluoro-1H-indol-3-yl)ethyl]propan-1-amine
CAS Number	2698331-33-6 ^{[画像:check]Y}
PubChem CID	156836218
ChemSpider	129221323
ChEMBL	ChEMBL5028990
Chemical and physical data
Formula	C₁₅H₂₁FN₂
Molar mass	248.345g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCN(CC)CCC1=CNC2=C1C=C(C=C2)F
InChI InChI=1S/C15H21FN2/c1-3-8-18(4-2)9-7-12-11-17-15-6-5-13(16)10-14(12)15/h5-6,10-11,17H,3-4,7-9H2,1-2H3 Key:QONMHCQBCANXJS-UHFFFAOYSA-N

5-Fluoro-EPT (5F-EPT, 5-fluoro-N-ethyl-N-propyltryptamine) is a psychedelic tryptamine derivative related to drugs such as EPT and 5-MeO-EPT. It acts as a potent full agonist at the 5-HT_2A receptor with an EC₅₀ of 5.54 nM and an efficacy of 104% (compared to serotonin). It produces a head-twitch response in animal studies, and is claimed to have antidepressant activity.^[1]

References

[edit ]

↑ WO 2021/168082, Kruegel AC, Sporn J, "Specific Tryptamines for use in the Treatment of Mood Disorders.", published 26 August 2021, assigned to Gilgamesh Pharmaceuticals, Inc..

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Psychedelics

Tryptamines

No ring subs.	CE-T DALT DBT DET (T-9) DiPT DMT DMT-d4 (D₄DMT) DMT-d10 (HLP004; CYB004) DPT EiPT EPT iPALT (ALiPT) MALT McPT MET MiPT MPT N-POM-DMT NMT PALT PiPT SPL028 (D₂-DMT) Tryptamine (T)
4-Hydroxytryptamines	1-Methylpsilocin (CMY, CMY-16) 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-NBnT 4-HO-NET 4-HO-NiPT 4-HO-NPT 4-HO-TMT 4-HO-5-MeO-DMT 4-HO-T (4-HT) Deupsilocin (HLP003; CYB003) Psilocin (4-HO-DMT; CX-59) Psilomethoxin (5-MeO-4-HO-DMT) 4-Phosphoryloxytryptamines: 5-Methoxypsilocybin (5-MeO-4-PO-DMT) 5-Methylpsilocybin (5-Me-4-PO-DMT) Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acyloxytryptamines: 4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET Luvesilocin (4-GO-DiPT; RE-104, FT-104)
5-Hydroxytryptamines	5-HO-MET Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acyloxytryptamines: O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT)
5-Methoxytryptamines	1-Acetyl-5-MeO-DMT 4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DMT-d4 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NiPT 5-MeO-NMT 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MeO-T (5-MT) ASR-3001 (5-MeO-iPALT) NB-5-MeO-DALT NB-5-MeO-MiPT
Other ring subs.	1-Benzoyl-DMT 2-Methyltryptamine 2,N,N-TMT (2-methyl-DMT) 4,N,N-TMT (4-methyl-DMT) 4-MeS-DMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-MeS-DMT 5-Nitro-T (Nitro-I) 5-PhO-T (OVT2) 5-N,N-TMT (5-methyl-DMT) 7,N,N-TMT (7-methyl-DMT) 5-MeO-2,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) 6-TFMO-DMT Bretisilocin (GM-2505; 5-fluoro-MET) HBL20016 (5-MeS-6-F-DMT) NBoc-DMT (NB-DMT)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) α,N,N-TMT (α-Me-DMT; Alpha-N) N-Hydroxy-AMT 5-Methoxy-α-alkyltryptamines: 5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET) Structure undisclosed: CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g., LSD) Ibogalogs (e.g., ibogainalog, tabernanthalog, Pharm-136) O-Methylnordehydrobufotenine Partial ergolines (e.g., NDTDI, RU-28306, CT-5252) Piperidinylethylindoles (e.g., pip-T) Pyrrolidinylethylindoles (e.g., pyr-T, 5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI, MSP-2020) Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI), NEtPhOH-THPI) Unknown psychedelic activity: β-Carbolines (e.g., 1-ethyl-6-hydroxytryptoline, 1-(2,4,5-trimethoxyphenyl)-6-chlorotryptoline)
Bioisosteres	Benzofurans (e.g., 5-MeO-DiBF (1-oxa-5-MeO-DiPT), dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT)) Benzothiophenes (e.g., 3-APBT (1-thia-AMT)) Indazolethylamines (e.g., AL-38022A, O-methyl-AL-34662) Indenylethylamines (e.g., C-DMT) Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175) MYCO-005 Unknown psychedelic activity: Quinolinylethylamines (e.g., mefloquine)

Phenethylamines

Scalines	2-Bromomescaline 4-D (4-trideuteromescaline) Allylescaline (AL) Alpha-D (α-D; α,α-dideuteromescaline) Alpha,Beta-D (α,β-D; α,β-dideuteromescaline) Beta-D (β-D; β,β-dideuteromescaline) Cyclopropylmescaline (CPM) Difluoroescaline (DFE) Difluoromescaline (DFM) N,N-Diformylmescaline Escaline (E) Fluoroescaline (FE) Fluoroproscaline (FP) N-Formylmescaline Isobuscaline (IB) Isoproscaline (IP) Mescaline (M; 3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline (ME) Methallylescaline (MAL) N-Methylmescaline (M-M) Proscaline (P) Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline (TFE) Trifluoromescaline (TFM) Thioscalines: 3-Thioasymbescaline (3-TASB) 3-Thioescaline (3-TE) 3-Thiomescaline (3-TM) 3-Thiometaescaline (3-TME) 4-Thioasymbescaline (4-TASB) 4-Thioescaline (4-TE) 4-Thiomescaline (4-TM) 5-Thioasymbescaline (5-TASB) Thiobuscaline (TB; 4-TB) Thioproscaline (TP; 4-TP) Desoxyscalines: 4-Desoxymescaline (desoxy, desoxymescaline) Others: Jimscaline Tomscaline
2C-x	2C-B 2CB-2OCD₃ 2CB-5OCD₃ 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-P 2C-Se 2C-Se-TFM 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: 2C-T 2C-T-2 2C-T-3 (2C-T-20) 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-21.5 2C-T-22 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-36 (2C-T-TFM; CYB210010; CYB2108) CYB2108D (deuterated 2C-T-36) 2C-O-x: 2C-O (2,4,5-TMPEA; TMPEA-2) 2C-O-4 2C-O-22 Others: 2C-B-AN 2C-DB 2C-G-x (e.g., 2C-G-3, 2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g., BOB, BOD, BOHB) HOT-x (e.g., HOT-2, HOT-7, HOT-17) N-Ethyl-2C-B TWEETIOs (e.g., 2CB-2-EtO, 2CD-2-EtO, 2CD-5-EtO, 2CE-5-EtO, 2CE-5iPrO, 2CT-5-EtO, 2CT2-2-EtO, 2CT7-2-EtO, ASR-2001 (2CB-5-PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-FP 3C-MAL 3C-P TMA (3C-M)
DOx	DOAM DOB DOBU DOC DOEF DOET DOH (2,5-DMA) DOI DOIB DOIP DOM DON DOPR DOTFM DOYN Aleph-x (DOT-x): Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx): MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others: DODB DODC DOM-NBOMe DOTMA Ganeshas (G-x) (e.g., Ganesha (G, G-0), G-3, G-5) MME (TMA2-5-EtO) N-Hydroxy-DOM
4C-x	4C-B 4C-D (Ariadne) 4C-I 4C-P (4C-Pr) 4C-T-2 4C-TFM
Ψ-PEA	2,4,6-TMPEA-NBOMe Ψ-2C-DFMO (ψ-2C-O-35) Ψ-2C-T-4 Ψ-DODFMO Ψ-DOM TMA-6 (Ψ-TMA-2)
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA EMDA-2 IDA Lophophine (MMDPEA) Lys-MDA MDA (tenamfetamine) MDHMA (FLEA; MDMOH) MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDA-3b MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-DragonFLY 2C-E-FLY 2C-EF-FLY 2C-I-FLY 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly Hemi/semi-FLY drugs: DOH-5-hemiFLY (semi-fly; SF) DOB-5-hemiFLY (bromo-semi-fly; B-SF)
25x-NB (NBOMes)	25x-NBOMe: 25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25O-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25E-NBOH 25I-NBOH 25x-NBF: 25B-NBF 25C-NBF 25I-NBF Others: 2,4,6-TMPEA-NBOMe 25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027
Others	25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F, F-2, F-22) Benzothiophenes (e.g., 5-APBT, 6-APBT) BMB-202 CT-5172 DMAs (e.g., 2,4-DMA, 3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA) PMA (4-MA) Thio-2Cs (e.g., 2C-5-TOET) Thio-DOx (e.g., 2-TOM, 5-TOET, 5-TOM, TOMSO) TMAs (e.g., TMA-3, TMA-4, TMA-5) ZDCM-04 (DOC-fenethylline) Structure undisclosed: HLP005 (CYB005)
Cyclized	1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline) 2-Aminoindanes (e.g., DOM-AI) 2-Aminotetralins (e.g., UH-232) 3-Benzazepines (e.g., lorcaserin) 3-Phenylpiperidines (e.g., LPH-5, LPH-48) Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g., LSD) Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA) Phenylcyclopropylamines (e.g., DMCPA, TMT) Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex) Pyridopyrroloquinoxalines (e.g., IHCH-7113) Z3517967757 ZC-B Unknown psychedelic activity: Aporphines and noraporphines (e.g., glaucine, 11-methoxyasimilobine, 2-hydroxy-11-(2-methylallyl)oxynoraporphine)

Lysergamides

No substitutions: Ergine (LSA, LA-111)
Isoergine (iso-LSA, iso-LA)

Amide-substituted lysergamides: DAL
DAM (DAM-57)
DiPLA
DPL
EcPLA
EiPLA
EPLA (LEP; LEP-57)
Ergometrine (ergonovine, ergobasine)
ETFELA
iPLA
LA-3Cl-SB (Cl-LSB)
LAE (LAE-32)
LAM
LAMPA
LAP
LME (LME-54)
LMP (LMP-55)
LPD (LPD-824)
LSB
LSD (LSD-25, METH-LAD; lysergide)
LSD-Pip
LSDP (DPL)
LSH (LAH)
LSM (LSM-775)
2-LSP
LSP (3-LSP)
LSZ (LA-SS-Az)
Lysergic acid pyrrolinide (LPN)
Methylergometrine (methylergonovine, methylergobasine)
MiPLA
TRALA-12 (didehydro-LSD; DDH-LSD)

1-Alkyllysergamides (prodrugs): Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

1-Acyllysergamides (prodrugs): 1-Formyl-LSD
1B-LSD
1BP-LSD
1Bz-LSD
1cP-AL-LAD
1cP-LSD
1cP-MiPLA
1D-AL-LAD
1D-LSD
1DD-LSD
1F-LSD
1Fe-LSD
1H-LSD
1P-AL-LAD
1P-ETH-LAD
1P-LSD
1P-MiPLA
1S-LSD
1SB-LSD (1BS-LSD; 1-TMSBz-LSD)
1T-AL-LAD
1T-LSD
1V-LSD
ALA-10 (1-acetyl-LAE; 1A-LAE)
ALD-52 (1-acetyl-LSD; 1A-LSD)

Bioisosteres: JRT (isotryptamine-LSD)

Others

9-Oxaergolines (e.g., RU-29717)
γ-Carbolines (e.g., tiflucarbine)
Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP, VCU-1012)
Dihydrobenzoxazines (e.g., efavirenz)
Phenoxyethylamines (e.g., CT-4719, ORG-37684)
Pyridopyrroloquinoxalines (e.g., IHCH-7113)
Quinazolinylethylamines (e.g., RH-34)

Natural sources

Phenethylamines: Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Echinopsis cacti (e.g., San Pedro, Peruvian torch)

v t e Tryptamines
Tryptamines	1-Benzoyl-DMT 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-Bromo-DMT 4-Fluoro-DMT 4-Fluoro-T 4-MeS-DMT 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-NiPT 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-Fluoro-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) CPI-CG-8 DALT DAT DBT Desformylflustrabromine DET (T-9) DMT-d10 (HLP004; CYB004) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 GR-46611 HBL20016 (5-MeS-6-F-DMT) HBL20017 (4-F-5-MeS-DMT) Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T, NBnT) N-(2-Cyanoethyl)tryptamine (CE-T) N-DEAOP-NET N-DEAOP-NMT N-Phosphonooxymethyl-DMT (N-POM-DMT) NAT NBoc-DMT (NB-DMT) NcPT NET/NETP NPT NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan T-NBOMe TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 ZCZ-011 Zolmitriptan
4-Hydroxytryptamines and esters/ethers	1-Methylpsilocin (CMY-16) 4-AcO-DALT 4-AcO-DET (ethacetin, ethylacybin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin; O-acetylpsilocin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiBT 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-DsBT 4-HO-EiBT (eibucin) 4-HO-EiPT 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-MET (metocin) 4-HO-McPT 4-HO-McPeT 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-NALT 4-HO-NBnT 4-HO-NcHT 4-HO-NET 4-HO-NiPT 4-HO-NBT (4-HO-NnBT) 4-HO-NPT 4-HO-NtBT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DET 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Deupsilocin (HLP003; CYB003) EB-002 (EB-373) Ethocybin (4-PO-DET; CEY-19) Luvesilocin (4-GO-DiPT; RE-104; FT-104) MSP-1014 Norbaeocystin (4-PO-T) Norpsilocin (4-HO-NMT) O-4310 (1-iPrO-6-F-psilocin) Psilocin (4-HO-DMT; CX-59) Psilocybin (4-PO-DMT; CY-39) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) RE-109 (4-GO-DMT)
5-Hydroxy- and 5-methoxytryptamines	1-Acetyl-5-MeO-DMT 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-DiMeO-DiPT (5,6-MeO-DiPT) 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-DMT 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	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin (N-Ac-O-Me-serotonin; N-Ac-5-MeO-T) Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301 (LY-156735)
α-Alkyltryptamines	1-Methyl-AMT 2,α-DMT (2-Me-AMT) 4-HO-αET 4-HO-αMT (MP-14) 4-Methyl-αET 4-Methyl-αMT (MP-809) 5-Chloro-αET (PAL-526) 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212; PAL-544) 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Me-αET α-Methyltryptophan (αMTP) α,N-DMT (N-Me-αMT; SKF-7024, Ro 3-1715) α,N,N-TMT (α-Me-DMT; Alpha-N) αET (etryptamine; Monase) αMT (Indopan; IT-290; 3-API; 3-IT) IPAP (α,N-DPT) N-Hydroxy-AMT Soclenicant (BNC-210; Ile–Trp) 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 β-Keto-α-alkyltryptamines: BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT
α-Ketotryptamines	AB-CHMIATA ADB-FUBIATA (ADB-FUBIACA) ADB-IACA AFUBIATA CH-FUBIATA (CH-FUBIACA) CH-HEXIATA CH-IACA CH-PIATA CH-PIATA N-(4-carboxybutyl) CH-PIATA N-(4-hydroxypentyl) CHM-FUBIATA
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, norharmine 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, Pharm-136, 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, LY-301317, 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, indoramin, 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) Z5247692566
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT (1-API; 1-IT; α-Me-isoT) isoDMT Isotryptamine (isoT) Ro60-0175 VER-3323 Zalsupindole (DLX-001, AAZ-A-154) Cyclized isotryptamines: DLX-0002700 JRT PNU-181731
Related compounds	1-Methylmedmain 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, 2MePI, 8MeO-2MePI, alosetron, gevotroline, latrepirdine, lurosetron, mebhydrolin, tiflucarbine) Amedalin Benzindopyrine Benzydamine 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)) BMS-505130 Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT, DMHT) I-32 IAL 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 Methylindolylethylpyridine (IN-399) Molindone Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan) Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134) Phenethylamines (e.g., phenethylamine, amphetamine) Piperazinylbenzisothiazoles (e.g., lurasidone, perospirone, tiospirone, ziprasidone) Piperidinylbenzimidazolines (e.g., benperidol, timiperone) 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 Roxindole (EMD-49980) 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)
See also: Phenethylamines Ergolines and lysergamides Psychedelics Simple tryptamines and common derivatives

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