Substituted tryptamine

Class of indoles From Wikipedia, the free encyclopedia

Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring system, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN1=RN2=Rα = H.
The structure of substituted tryptamines with all positions labeled.

Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids are found in fungi, plants and animals; and sometimes used by humans for the neurological or psychotropic effects of the substance. Prominent examples of tryptamine alkaloids include psilocybin (from "psilocybin mushrooms") and DMT. In South America, dimethyltryptamine is obtained from numerous plant sources, like chacruna, and it is often used in ayahuasca brews. Many synthetic tryptamines have also been made, including the migraine drug sumatriptan, and psychedelic drugs. A 2022 study has found the variety of tryptamines present in wild mushrooms may affect the therapeutic impact.[1]

The tryptamine structure, in particular its indole ring, may be part of the structure of some more complex compounds, for example cyclized tryptamines like LSD, ibogaine, harmaline, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Alexander Shulgin and Ann Shulgin in 1997 under the title TiHKAL (Tryptamines I Have Known and Loved).[2]

Use and effects

The doses, potencies, durations, and effects of psychedelic tryptamines have been reviewed by Alexander Shulgin and other authors.[3][4][5][6][2][7][8][9][10][11]

Ring-unsubstituted tryptamines

More information Compound, Chemical name ...
Oral doses and durations of ring-unsubstituted tryptamines
CompoundChemical nameDoseDuration
Tryptamine (T)Tryptamine>100 mga–
NMTN-MethyltryptamineUnknownb–
NETN-EthyltryptamineUnknownUnknown
NiPTN-IsopropyltryptamineUnknownUnknown
NsBTN-sec-Butyltryptamine25–75 mg"Short"
NtBTN-tert-Butyltryptamine5–20 mgUnknown
NATN-Amyltryptamine>100 mg–
NHTN-Hexyltryptamine>100 mg–
DMTN,N-Dimethyltryptamine>350–1,000 mgc–
DETN,N-Diethyltryptamine50–150 mg2–4 hours
DPTN,N-Dipropyltryptamine100–250 mg2–4 hours
DiPTN,N-Diisopropyltryptamine25–100 mg (15–150 mg+)4–8 hours
DALTN,N-Diallyltryptamine60–80 mg<3 hours
DBTN,N-Dibutyltryptamine≥100 mgUnknown
DATN,N-DiamyltryptamineUnknownUnknown
DHTN,N-Dihexyltryptamine>100 mg–
METN-Methyl-N-ethyltryptamine80–100 mgUnknown
MPTN-Methyl-N-propyltryptamine>50 mgUnknown
MiPTN-Methyl-N-isopropyltryptamine10–25 mg3–4 hours
MALTN-Methyl-N-allyltryptamine25–50 mgUnknown
MBTN-Methyl-N-butyltryptamine250–400 mg4–6 hours
MsBTN-Methyl-N-sec-butyltryptamine250–400 mgUnknown
EPTN-Ethyl-N-propyltryptamineUnknownUnknown
EiPTN-Ethyl-N-isopropyltryptamine24–40 mg4–6 hours
PiPTN-Propyl-N-isopropyltryptamineUnknownUnknown
Pyr-TN,N-TetramethylenetryptamineUnknownUnknown
Pip-TN,N-PentamethylenetryptamineUnknownUnknown
Mor-T3-(2-Morpholinoethyl)indoleUnknowndUnknown
Footnotes: a = Tryptamine is not orally active, but is active intravenously at a dose of 250 mg with a very short duration. b = NMT is not orally active, but is said to be active smoked at a dose of 50 to 120 mg with a duration of seconds to minutes. Also reportedly orally active with an MAOITooltip monoamine oxidase inhibitor. c = DMT is active parenterally at doses of 50 to 100 mg (2–100 mg) smoked, intramuscularly, or subcutaneously and at doses of 4 to 30 mg intravenously (bolus), with a duration of <1 hour or 5–20 minutes. For continuous intravenous infusion, the dose is 0.6 to 2.4 mg/minute. Also orally active with an MAOI (as in ayahuasca or pharmahuasca), with a typical dose of 50 mg (range 20–120 mg) and a duration of 4 to 6 hours. d = Mor-T was inactive at a dose of 30 mg by intramuscular injection. Refs: [3][4][2][7][8][9][11] Individual: [12][13][14][15][16][17][18][19][20][21][22][23]
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4-Hydroxytryptamines

More information Compound, Chemical name ...
Oral doses and durations of 4-hydroxytryptamines
CompoundChemical nameDoseDuration
4-HT (4-HO-T)4-HydroxytryptamineUnknownUnknown
Norbaeocystin (4-PO-T)4-PhosphoryloxytryptamineUnknownUnknown
Norpsilocin (4-HO-NMT)4-Hydroxy-N-methyltryptamineUnknownUnknown
Baeocystin (4-PO-NMT)4-Phosphoryloxy-N-methyltryptamine4–10 mgaUnknown
Psilocin (4-HO-DMT)4-Hydroxy-N,N-dimethyltryptamine10–20 mg (5–40 mg+)3–6 hours
Psilocybin (4-PO-DMT)4-Phosphoryloxy-N,N-dimethyltryptamine10–20 mg (5–40 mg+)3–6 hours
4-AcO-DMT (psilacetin)4-Acetoxy-N,N-dimethyltryptamine10–30 mg3–8 hours
4-PrO-DMT4-Propionyloxy-N,N-dimethyltryptamineUnknownUnknown
4-HO-DET (ethocin)4-Hydroxy-N,N-diethyltryptamine10–25 mg4–6 hours
Ethocybin (4-PO-DET)4-Phosphoryloxy-N,N-diethyltryptamine15–30 mg4–6 hours
4-HO-DPT (deprocin)4-Hydroxy-N,N-dipropyltryptamine>20 mg5–8 hours
4-HO-DiPT (iprocin)4-Hydroxy-N,N-diisopropyltryptamine12–20 mg (3–30 mg+)2–3 hours
4-AcO-DiPT (ipracetin)4-Acetoxy-N,N-diisopropyltryptamine6–10 mgUnknown
Luvesilocin (4-GO-DiPT)4-Glutaryloxy-N,N-diisopropyltryptamineUnknownbUnknownb
4-HO-DALT (daltocin)4-Hydroxy-N,N-diallyltryptamineUnknownUnknown
4-HO-DBT4-Hydroxy-N,N-dibutyltryptamine>20 mgUnknown
4-HO-DiBT4-Hydroxy-N,N-diisobutyltryptamine>20 mgUnknown
4-HO-DtBT4-HydroxyN,N-di-tert-butyltryptamineUnknownUnknown
4-HO-MET (metocin)4-Hydroxy-N-methyl-N-ethyltryptamine10–20 mg (2–45 mg+)4–6 hours
4-HO-MPT (meprocin)4-Hydroxy-N-methyl-N-propyltryptamine8–30 mgUnknown
4-HO-MiPT (miprocin)4-Hydroxy-N-methyl-N-isopropyltryptamine12–25 mg (6–30 mg)4–6 hours
4-HO-MALT (maltocin)4-Hydorxy-N-methyl-N-allyltryptamineUnknownUnknown
4-HO-MtBT4-Hydroxy-N-methyl-N-tert-butyltryptamine>15 mgUnknown
4-HO-EPT (eprocin)4-Hydroxy-N-ethyl-N-propyltryptamineUnknownUnknown
4-HO-EiPT4-Hydroxy-N-ethyl-N-isopropyltryptamineUnknownUnknown
4-HO-PiPT (piprocin)4-Hydroxy-N-propyl-N-isopropyltryptamineUnknownUnknown
4-HO-TMT4-Hydroxy-N,N,N-trimethyltryptamineUnknownUnknown
Aeruginascin (4-PO-TMT)4-Phosphoryloxy-N,N,N-trimethyltryptamineUnknownUnknown
4-HO-pyr-T4-Hydroxy-N,N-tetramethylenetryptamine>20 mgUnknown
Footnotes: a = Baeocystin has conflicting reports, some say that it's active and some say that it's inactive. b = Luvesilocin is known to be active subcutaneously at doses of 5 to 40 mg with an average duration of 3.6 hours. Refs: [3][4][2][7][8][9][11][10] Individual: [14][15][24][25][26]
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5-Hydroxytryptamines

More information Compound, Chemical name ...
Oral doses and durations of 5-hydroxytryptamines
CompoundChemical nameDoseDuration
Serotonin (5-HT, 5-HO-T)5-Hydroxytryptamine>100 mga–
N-Methylserotonin (norbufotenin; 5-HO-NMT)5-Hydroxy-N-methyltryptamineUnknownUnknown
Bufotenin (5-HO-DMT)5-Hydroxy-N,N-dimethyltryptamine>100 mgb–
O-Acetylbufotenin (5-AcO-DMT)5-Acetoxy-N,N-dimethyltryptamineUnknownUnknown
O-Pivalylbufotenin (5-t-BuCO-DMT)5-Pivaloxy-N,N-dimethyltryptamineUnknownUnknown
5-HO-DET5-Hydroxy-N,N-diethyltryptamineUnknownUnknown
5-HO-DPT (DiPS, NDPS)5-Hydroxy-N,N-dipropyltryptamineUnknownUnknown
5-HO-DiPT5-Hydroxy-N,N-diisopropyltryptamineUnknownUnknown
5-HO-MET5-Hydroxy-N-methyl-N-ethyltryptamineUnknownUnknown
Footnotes: a = Serotonin does not cross the blood–brain barrier and is not psychoactive. b = Bufotenin is not orally active, but is active intravenously at doses of 8 to 16 mg with a duration of 1 to 2 hours and is active via insufflation and other parenteral routes. Refs: [3][4][2][11] Individual: [27][28][29][30]
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5-Methoxytryptamines

More information Compound, Chemical name ...
Oral doses and durations of 5-methoxytryptamines
CompoundChemical nameDoseDuration
5-MT (5-MeO-T)5-MethoxytryptamineUnknownUnknown
5-MeO-NMT5-Methoxy-N-methyltryptamineUnknownUnknown
5-MeO-NET5-Methoxy-N-ethyltryptamineUnknownUnknown
5-MeO-NiPT5-Methoxy-N-isopropyltryptamineUnknownUnknown
5-MeO-DMT (mebufotenin)5-Methoxy-N,N-dimethyltryptamine>35 mga–
5-MeO-DET5-Methoxy-N,N-diethyltryptamine1–3 mg3–4 hours
5-MeO-DPT5-Methoxy-N,N-dipropyltryptamine6–10 mg2–4 hours
5-MeO-DiPT5-Methoxy-N,N-diisopropyltryptamine6–12 mg4–8 hours
5-MeO-DALT5-Methoxy-N,N-diallyltryptamine12–25 mg2–4 hours
5-MeO-DBT5-Methoxy-N,N-dibutyltryptamineUnknownUnknown
5-MeO-DsBT5-Methoxy-N,N-di-sec-butyltryptamineUnknownUnknown
5-MeO-MET5-Methoxy-N-methyl-N-ethyltryptamineUnknownUnknown
5-MeO-MPT5-Methoxy-N-methyl-N-propyltryptamineUnknownUnknown
5-MeO-MiPT5-Methoxy-N-methyl-N-isopropyltryptamine4–6 mg (0.5–20 mg+)4–6 hours
5-MeO-MALT5-Methoxy-N-methyl-N-allyltryptamineUnknownUnknown
5-MeO-MsBT5-Methoxy-N-methyl-N-sec-butyltryptamine10–30 mg3–4 hours
5-MeO-EPT5-Methoxy-N-ethyl-N-propyltryptamineUnknownUnknown
5-MeO-EiPT5-Methoxy-N-ethyl-N-isopropyltryptamineUnknownUnknown
5-MeO-PiPT5-Methoxy-N-propyl-N-isopropyltryptamineUnknownUnknown
5-MeO-iPALT (ASR-3001)5-Methoxy-N-isopropyl-N-allyltryptamine8–14 mg1.5–2.5 hours
5-MeO-pyr-T5-Methoxy-N,N-tetramethylenetryptamine0.5–2 mgSeveral hours
Melatonin (5-MeO-NAcT)5-Methoxy-N-acetyltryptamine1–10 mgbA few hours
Footnotes: a = 5-MeO-DMT is not orally active, but is active at a dose of 2 to 20 mg smoked or 2 to 3 mg intravenously, with a duration of 5 to 20 minutes. Also orally active with an MAOITooltip monoamine oxidase inhibitor at doses of 10 to 25 mg. b = Melatonin is not a psychedelic but a hypnotic and is non-hallucinogenic at doses of up to 1,200 mg. Refs: [3][4][2][7][8][9][11] Individual: [15][19][31]
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α-Alkyltryptamines

More information Compound, Chemical name ...
Oral doses and durations of α-alkyltryptamines
CompoundChemical nameDoseDuration
AMT (α-methyl-T; Indopan)aα-Methyltryptamine15–40 mg12–16 hours
AET (α-ethyl-T; etryptamine; Monase)bα-Ethyltryptamine100–160 mg6–8 hours
α,N-DMT (N-methyl-AMT)cα-Methyl-N-methyltryptamine50–100 mg6–8 hours
α,N,N-TMT (N,N-dimethyl-AMT)α,N,N-TrimethyltryptamineUnknowndUnknown
2,α-DMT (2-methyl-AMT)2-Methyl-α-methyltryptamine300–500 mg7–10 hours
4-HO-AMT (MP-14)4-Hydroxy-α-methyltryptamine15–20 mg+Unknown
4-Methyl-AMT (MP-809)4-Methyl-α-methyltryptamine20–60 mg+Unknown
5-Fluoro-AMT (PAL-212, PAL-544)5-Fluoro-α-methyltryptamine25 mg+>9 hours
5-Chloro-AMT (PAL-542)5-Chloro-α-methyltryptamineUnknownUnknown
5-Fluoro-AET (PAL-545)5-Fluoro-α-ethyltryptamineUnknownUnknown
5-Chloro-AET (PAL-526)5-Chloro-α-ethyltryptamineUnknownUnknown
6-Fluoro-AMT6-Fluoro-α-methyltryptamine25–75 mg"Long"
α-Methylserotonin (AMS; 5-HO-AMT)α-Methyl-5-hydroxytryptamineUnknownUnknown
α,O-DMS (5-MeO-AMT)α-Methyl-5-methoxytryptamine2.5–5 mg (0.5–15 mg)12–18 hours
α,N,O-TMS (5-MeO-N-methyl-AMT)α-Methyl-5-methoxy-N-methyltryptamine10–20 mg6–8 hours
α,N,N,O-TeMS (5-MeO-N,N-dimethyl-AMT)5-Methoxy-α,N,N-trimethyltryptamineUnknownUnknown
5-MeO-AETα-Ethyl-5-methoxytryptamine~70 mgSeveral hours
Bk-NM-AMT (β-keto-N-methyl-AMT)eα-Methyl-β-keto-N-methyltryptamineUnknownUnknown
Footnotes: a = AMT is a not only a psychedelic but is also a stimulant and entactogen. b = AET is an entactogen and stimulant and is not a psychedelic. c = α,N-DMT is a stimulant and is not a psychedelic or entactogen. d = α,N,N-TMT has been reported to be an active psychedelic orally but to be much less potent than AMT. e = Bk-NM-AMT is expected to be an entactogen and stimulant but not a psychedelic. Refs: [3][4][2][7][8][11] Individual: [32][33]
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Other tryptamines

More information Compound, Chemical name ...
Oral doses and durations of other tryptamines
CompoundChemical nameDoseDuration
Lespedamine (1-MeO-DMT)1-Methoxy-N,N-dimethyltryptamineUnknownUnknown
2-Methyl-DMT2-Methyl-N,N-dimethyltryptamine50–100 mg4–6 hours
2-Methyl-DET2-Methyl-N,N-diethyltryptamine80–120 mg6–8 hours
4-MeO-DMT4-Methoxy-N,N-dimethyltryptamineUnknownUnknown
4-MeO-DET4-Methoxy-N,N-diethyltryptamine>30 mgUnknown
4-MeO-DiPT4-Methoxy-N,N-diisopropyltryptamineUnknownUnknown
4-MeO-MiPT4-Methoxy-N-methyl-N-isopropyltryptamines20–30 mg4–6 hours
4,5-MDO-DMT4,5-Methylenedioxy-N,N-dimethyltryptamineUnknownUnknown
4,5-MDO-DiPT4,5-Methylenedioxy-N,N-diisopropyltryptamine>25 mgUnknown
5-Fluoro-DMT5-Fluoro-N,N-dimethyltryptamineUnknownUnknown
5-Chloro-DMT5-Chloro-N,N-dimethyltryptamineUnknownUnknown
5-Bromo-DMT5-Bromo-N,N-dimethyltryptamineUnknownaUnknown
Bretisilocin (5-fluoro-MET)5-Fluoro-N-methyl-N-ethyltryptamineUnknownbUnknownb
5-MeO-2-TMT5-Methoxy-2-methyl-N,N-dimethyltryptamine75–150 mg5–10 hours
5-MeS-DMT5-Methylthio-N,N-dimethyltryptamineUnknowncUnknownc
5,6-MeO-MiPT5,6-Dimethoxy-N-methyl-N-isopropyltryptamine>75 mgUnknown
5,6-MDO-DMT5,6-Methylenedioxy-N,N-dimethyltryptamine>5 mgUnknown
5,6-MDO-DiPT5,6-Methylenedioxy-N,N-diisopropyltryptamineUnknownUnknown
5,6-MDO-MiPT5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine>50–60 mgUnknown
6-Fluoro-DMT6-Fluoro-N,N-dimethyltryptamineUnknownUnknown
6-Fluoro-DET6-Fluoro-N,N-diethyltryptamine>80 mgUnknown
6-HO-DMT6-Hydroxy-N,N-dimethyltryptamine>80 mgUnknown
6-HO-DET6-Hydroxy-N,N-diethyltryptamine≥10 mgd3–4 hoursd
6-MeO-DMT6-Methoxy-N,N-dimethyltryptamineUnknownUnknown
6-MeO-DiPT6-Methoxy-N,N-diisopropyltryptamine>50 mgUnknown
6-MeO-MiPT6-Methoxy-N-methyl-N-isopropyltryptamine>50 mgUnknown
7-HO-DMT7-Hydroxy-N,N-dimethyltryptamineUnknownUnknown
7-MeO-DMT7-Methoxy-N,N-dimethyltryptamineUnknownUnknown
7-MeO-DiPT7-Methoxy-N,N-diisopropyltryptamine>70 mgUnknown
7-MeO-MiPT7-Methoxy-N-methyl-N-isopropyltryptamine>70 mgUnknown
Footnotes: a = 5-Bromo-DMT is active via smoking at a dose of 20 to 50 mg. b = Bretisilocin is active intravenously with a dose range of 10 to 20 mg and a duration of 60 to 90 minutes. c = 5-MeS-DMT's oral dose and duration are unknown, but smoked the dose is 15 to 30 mg and the duration is 10 to 30 minutes or <1 hour. d = Controversial and uncertain. Refs: [3][4][2][9][11] Individual: [34][35][21]
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Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

More information Compound, 5-HT1A ...
Serotonin receptor affinities (Ki, nM) of selected psychedelic tryptamines (Jain et al., 2025)[36]
Compound5-HT1A5-HT1B5-HT1D5-HT1E5-HT2A5-HT2B5-HT2C5-HT35-HT5A5-HT65-HT7SERT
DMT269447117380380112257–2,090275692,400
Psilocin3721919833920025245–44779872,570
Psilocybin5,250–195–8514793,090––776––
4-AcO-MALT977–87141769225631––6617943,090
Bufotenin8.35922252246.2209166302188.91,120
5-MeO-DMT10912157520015490–589254.4–
5-MeO-DiPT170–871–32446–––2,190––
5-MeO-DALT171,020549774571002,240––162604,470
5-MeO-EiPT541,170174–1,62298–––4076615,620
LSD5.9213.51358.55.517–1.8168.5–
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More information Compound, 5-HT1A ...
Serotonin receptor affinities (Ki, nM) of selected psychedelic tryptamines (Ray, 2010)[37]
Compound5-HT1A5-HT1B5-HT1D5-HT1E5-HT2A5-HT2B5-HT2C5-HT35-HT5A5-HT65-HT7SERT
DMT>10,000>10,000934562,323108335>10,0006114878833,742
DPT328546192,3382,579421,567>10,0004,3734,543284157
DiPT121>10,0003,742>10,000>10,000399>10,000>10,000>10,000>10,0003,4231,258
Psilocin6330519443404.7141>10,000707272852
5-MeO-DMT1.9746.33602,0113,884538>10,000277363.92,032
5-MeO-DiPT1325,1371,718>10,000>10,000163>10,000>10,000>10,000>10,0001,2312,531
5-MeO-MiPT12303233,496448592,186>10,000953130206,409
6-Fluoro-DMT3932185546186630674>10,0009612641145
5-MeO-2-TMT200>10,0002501,800>10,000?4,020?10,45060145>10,000
EMDT170>10,000290520>10,000?1,810?4,62016300>10,000
Ibogaine>10,000>10,000>10,000?14,142?>10,000>10,000???549
LSD7.33.97.893113031>10,00096.96.6>10,000
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Chemistry

Synthesis

The chemical syntheses of numerous tryptamines have been described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved).[2] A well-known and widely used synthetic approach for making tryptamines is the Speeter–Anthony route, which starts with indole.[38][39][40] Other tryptamine synthesis routes have also been described, for instance starting with tryptamine rather than indole.[38][39] The chemical syntheses of the psychedelic tryptamines bufotenin (5-HO-DMT) and 5-MeO-DMT (mebufotenin) have been comprehensively reviewed.[41]

List of substituted tryptamines

More information Structure, Name ...
Structure Name Origin Ring sub. RN1 RN2 Chemical name CAS #
Tryptamine (T)Animals, plants, fungiHHH3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine61-54-1
NMTPlantsHHCH3N-methyltryptamine61-49-4
2-HO-NMTPlants2-OHHCH32-hydroxy-N-methyltryptamine106987-89-7
5-MeO-NMTPlants5-OCH3HCH35-methoxy-N-methyltryptamine2009-03-2
Serotonin (5-HT)Animals, plants5-OHHH5-hydroxytryptamine50-67-9
N-Methylserotonin (NMS; norbufotenin; 5-HO-NMT)Plants5-OHHCH35-hydroxy-N-methyltryptamine1134-01-6
Bufotenin (5-HO-DMT)Animals, plants, fungi5-OHCH3CH35-hydroxy-N,N-dimethyltryptamine487-93-4
Bufotenidine (5-HTQ)Amphibians5-O−(CH3)33-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate487-91-2
Bufoviridine (5-SO-DMT)Amphibians5-SOCH3CH35-sulfooxy-N,N-dimethyltryptamine16369-08-7
Melatonin (5-MeO-NAcT)Animals, plants, microbes5-OCH3HO=C-CH35-methoxy-N-acetyltryptamine73-31-4
N-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT)Animals5-OHHO=C-CH35-hydroxy-N-acetyltryptamine1210-83-9
6-HydroxymelatoninAnimals5-OCH3, 6-OHHO=C-CH3N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide2208-41-5
4-Hydroxytryptamine (4-HT)Fungi4-OHHH4-hydroxytryptamine570-14-9
4-HO-NMTFungi4-OHHCH34-hydroxy-N-methyltryptamine28363-70-4
Psilocin (4-HO-DMT)Fungi4-OHCH3CH34-hydroxy-N,N-dimethyltryptamine520-53-6
4-HO-TMTFungi4-OHCH3CH34-hydroxy-N,N,N-trimethyltryptammonium262285-41-6
Norbaeocystin (4-PO-T)Fungi4-OPO3H2HH4-phosphoryloxy-tryptamine21420-59-7
Baeocystin (4-PO-NMT)Fungi4-OPO3H2HCH34-phosphoryloxy-N-methyl-tryptamine21420-58-6
Psilocybin (4-PO-DMT)Fungi4-OPO3H2CH3CH34-phosphoryloxy-N,N-dimethyltryptamine520-52-5
Aeruginascin (4-PO-TMT)Fungi4-OPO3H2(CH3)3[3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate114264-95-8
DMTAnimals, plantsHCH3CH3N,N-dimethyltryptamine61-50-7
Lespedamine (1-MeO-DMT)Plants1-OCH3CH3CH31-methoxy-N,N-dimethyltryptamine4335-93-7
5-MeO-DMT (mebufotenin)Animals, plants5-OCH3CH3CH35-methoxy-N,N-dimethyltryptamine1019-45-0
5-Bromo-DMTMarine sponges, invertebrates5-BrCH3CH35-bromo-N,N-dimethyltryptamine17274-65-6
6-BromotryptamineMarine invertebrates6-BrHH6-bromotryptamine96624-18-9
5,6-DibromotryptamineMarine invertebrates5,6-BrHH5,6-dibromotryptamine
5,6-Dibromo-NMTMarine invertebrates5,6-BrHCH35,6-dibromo-N-methyltryptamine
5,6-Dibromo-DMTMarine sponges, invertebrates5,6-BrCH3CH35,6-dibromo-N,N-dimethyltryptamine72853-80-6
Desformylflustrabromine (dFBr)Marine invertebrates2-(α,α-dimethylallyl), 6-BrHCH32-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine474657-72-2
Convolutindole AMarine invertebrates2,4,6-Br, 1,7-OCH3CH3CH31,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine443356-86-3
1-Methyltryptamine (1-MT) artificial 1-CH3 H H 1-Methyltryptamine 7518-21-0
4-Methoxytryptamine (4-MeO-T) artificial 4-OCH3 H H 4-Methoxytryptamine 3610-35-3
4-Fluorotryptamine (4-FT) artificial 4-F H H 4-Fluorotryptamine ?
5-Methyltryptamine (5-MT) artificial 5-CH3 H H 5-Methyltryptamine 1821-47-2
5-Fluorotryptamine (5-FT) artificial 5-F H H 5-Fluorotryptamine 576-16-9
5-Chlorotryptamine (5-Cl-T) artificial 5-Cl H H 5-Chlorotryptamine ?
5-Bromotryptamine (5-Br-T) artificial 5-Br H H 5-Bromotryptamine ?
6-Methyltryptamine (6-MT) artificial 6-CH3 H H 6-Methyltryptamine ?
6-Hydroxytryptamine (6-HT) artificial 6-OH H H 6-Hydroxytryptamine 443-31-2
6-Methoxytryptamine (6-MeO-T) artificial 6-OCH3 H H 6-Methoxytryptamine 3610-36-4
6-Fluorotryptamine (6-FT) artificial 6-F H H 6-Fluorotryptamine 575-85-9
7-Methyltryptamine (7-MT) artificial 7-CH3 H H 7-Methyltryptamine ?
7-Methoxytryptamine (7-MeO-T) artificial 7-OCH3 H H 7-Methoxytryptamine ?
7-Chlorotryptamine (7-Cl-T) artificial 7-Cl H H 7-Chlorotryptamine 3804-16-8
Acetryptine (5-AT) artificial 5-COCH3 H H 5-Acetyltryptamine 3551-18-6
5-PhO-T artificial 5-OC6H5 H H 5-Phenoxytryptamine 31363-70-9
5-BT artificial 5-OCH2C6H5 H H 5-Benzyloxytryptamine 20776-45-8
5-CT artificial 5-CONH2 H H 5-Carboxamidotryptamine 74885-09-9
5-Nitrotryptamine (Nitro-I) artificial 5-NO2 H H 5-Nitrotryptamine 55747-72-3
5-NOTartificial5-O(CH2)8CH3HH5-Nonyloxytryptamine157798-12-4
2-Methyl-5-hydroxytryptamine artificial 2-CH3, 5-OH H H 3-(2-aminoethyl)-2-methyl-1H-indol-5-ol 78263-90-8
NET artificial H H CH2CH3 N-ethyltryptamine 61-53-0
NiPT artificial H H CH(CH3)2 N-isopropyltryptamine 14121-10-9
NcPT artificial H H C3H5 N-cyclopropyltryptamine
NsBT artificial H H CH(CH3)CH2CH3 N-sec-butyltryptamine
NtBT artificial H H C(CH3)3 N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine 1344092-44-9
NAT artificial H H (CH2)4CH3 N-[2-(1H-indol-3-yl)ethyl]pentan-1-amine
NHT artificial H H (CH2)5CH3 N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine
N-Benzyltryptamine (NBnT) artificial H H CH2C6H5 N-benzyltryptamine 15741-79-4
T-NBOMe (NBOMeT) artificial H H CH2C6H4(o-OCH3) N-(2-methoxybenzyl)tryptamine 418781-81-4
4-HO-NET artificial 4-OH CH2CH3 H 4-hydroxy-N-ethyltryptamine
4-HO-NPT artificial 4-OH CH(CH3)2 H 4-hydroxy-N-propyltryptamine
4-HO-NiPT artificial 4-OH CH(CH3)2 H 4-hydroxy-N-isopropyltryptamine
4-HO-NALT[42] artificial 4-OH H H2C=CH-CH2 4-hydroxy-N-allyltryptamine
4-HO-NBT (4-HO-NnBT) artificial 4-OH H (CH2)3CH3 4-hydroxy-N-n-butyltryptamine
4-HO-NiBT artificial 4-OH H CH2CH(CH3)2 4-hydroxy-N-isobutyltryptamine
4-HO-NsBT artificial 4-OH H CH(CH3)CH2CH3 4-hydroxy-N-sec-butyltryptamine
4-HO-NtBT artificial 4-OH H C(CH3)3 4-hydroxy-N-tert-butyltryptamine
4-HO-NBnT artificial 4-OH H CH2C6H5 4-hydroxy-N-benzyltryptamine
4-HO-NcHT artificial 4-OH H C6H11 4-hydroxy-N-cyclohexyltryptamine
5-MeO-NET artificial 5-OCH3 H CH2CH3 5-methoxy-N-ethyltryptamine 1019-46-1
5-MeO-NiPT artificial 5-OCH3 H CH(CH3)2 5-methoxy-N-isopropyltryptamine 109921-55-3
5-MeO-NsBT artificial 5-OCH3 H CH(CH3)CH2CH3 5-methoxy-N-sec-butyltryptamine
5-MeO-NBnT artificial 5-OCH3 H CH2C6H5 5-methoxy-N-benzyltryptamine 25100-31-6
5-MeO-T-NBOMe artificial 5-OCH3 H CH2C6H4(o-OCH3) 5-methoxy-N-(ortho-methoxybenzyl)tryptamine 1335331-37-7
5-MeO-T-NB3OMe [43] artificial 5-OCH3 H CH2C6H4(m-OCH3) 5-methoxy-N-(meta-methoxybenzyl)tryptamine 1648553-42-7
5-MeO-NBpBrT artificial 5-OCH3 H CH2C6H4(p-Br) N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine 155639-13-7
5-MeO-34MPEMT [44] artificial 5-OCH3 CH3 CH2CH2C6H3(p,m-OCH3) N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
Idalopirdine artificial 6-F H CH2C6H4(m-OCH2CF2CF2H) 2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine 467459-31-0
Z2876442907[45] artificial 4-CH3 H CH2(C3HNS)-COOCH2CH3 ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate
Cis-2',5'-dimethyl-4-HO-azt-T [46]artificial4-OHcis-(CHCH3)CH2(CHCH3)3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol
Pyr-TartificialH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole14008-96-9
4-HO-pyr-Tartificial4-OH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol63097-26-7
Cis-2',5'-dimethyl-4-HO-pyr-T [46]artificial4-OHcis-(CHCH3)CH2CH2(CHCH3)3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol
5-MeO-pyr-Tartificial5-OCH3(CH2)45-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole3949-14-2
4-F-5-MeO-pyr-Tartificial4-F-5-OCH3(CH2)44-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole344790-93-8
Pip-TartificialH(CH2)53-(2-Piperidin-1-ylethyl)-1H-indole26628-87-5
5-MeO-pip-Tartificial5-OCH3(CH2)55-Methoxy-3-(2-piperidin-1-ylethyl)-1H-indole
Mor-TartificialH?3-[2-(Morpholin-4-yl)ethyl]-1H-indole25262-59-3
5-MeO-mor-Tartificial5-OCH3?5-Methoxy-3-[2-(morpholin-4-yl)ethyl]-1H-indole3949-13-1
IsoqT[47]artificialH?3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-1H-indole
5-MeO-IsoqTartificial5-OCH3?3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-5-methoxy-1H-indole
IndolylethylfentanylartificialH(CH2)5-4-N(COCH2CH3)C6H5N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide58399-46-5
MET artificial H CH3 CH2CH3 N-Methyl-N-ethyltryptamine 5599-69-9
MPT artificial H CH3 CH2CH2CH3 N-Methyl-N-propyltryptamine 850032-72-3
MiPT artificial H CH3 CH(CH3)2 N-Methyl-N-isopropyltryptamine 96096-52-5
McPT artificial H CH3 C3H5 N-Methyl-N-cyclopropyltryptamine 1373918-63-8
EcPT artificial H CH2CH3 C3H5 N-ethyl-N-cyclopropyltryptamine
PcPT artificial H CH2CH2CH3 C3H5 N-propyl-N-cyclopropyltryptamine
iPcPT artificial H CH(CH3)2 C3H5 N-isopropyl-N-cyclopropyltryptamine
DcPT artificial H C3H5 C3H5 N,N-dicyclopropyltryptamine 1373918-62-7
MBT artificial H CH3 (CH2)3CH3 N-Methyl-N-butyltryptamine 848130-12-1
MsBT artificial H CH3 CH(CH3)CH2CH3 N-Methyl-N-sec-butyltryptamine
MiBT artificial H CH3 CH2CH(CH3)2 N-Methyl-N-iso-butyltryptamine
McPMT artificial H CH3 CH2C3H5 N-Methyl-N-(cyclopropylmethyl)tryptamine
Deudimethyltryptamine (DMT-d10; likely CYB004) artificial H CH3 CH3 α,α,β,β-Tetradeutero-N,N-bis(trideuteriomethyl)tryptamine 2742678-60-8
SPL028 (D2-DMT) artificial H CH3 CH3 α,α-Dideutero-N,N-dimethyltryptamine ?
DET artificial H CH2CH3 CH2CH3 N,N-diethyltryptamine 61-51-8
EPT artificial H CH2CH3 CH2CH2CH3 N-Ethyl-N-propyltryptamine 850032-68-7
EiPT artificial H CH2CH3 CH(CH3)2 N-Ethyl-N-isopropyltryptamine 848130-11-0
DPT artificial H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine 61-52-9
PiPT artificial H CH2CH2CH3 CH(CH3)2 N-Propyl-N-isopropyltryptamine 1354632-00-0
DiPT artificial H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine 14780-24-6
EBT artificial H CH2CH3 (CH2)3CH3 N-ethyl-N-butyltryptamine
PBT artificial H CH2CH2CH3 (CH2)3CH3 N-propyl-N-butyltryptamine
iPsBT artificial H CH(CH3)2 CH(CH3)CH2CH3 N-isopropyl-N-sec-butyltryptamine
DBT artificial H (CH2)3CH3 (CH2)3CH3 N,N-dibutyltryptamine 15741-77-2
DiBT artificial H CH2CH(CH3)2 CH2CH(CH3)2 N,N-diisobutyltryptamine 63938-64-7
DsBT artificial H CH(CH3)CH2CH3 CH(CH3)CH2CH3 N,N-disecbutyltryptamine
DAT artificial H (CH2)4CH3 (CH2)4CH3 N,N-diamyltryptamine
DHT artificial H (CH2)5CH3 (CH2)5CH3 N,N-dihexyltryptamine
MALT artificial H CH3 H2C=CH-CH2 N-methyl-N-allyltryptamine 1366416-29-6
DALT artificial H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine 60676-77-9
PALT artificial H H2C=CH-CH2 CH2CH2CH3 N-propyl-N-allyltryptamine 2686297-71-0
iPALT (ALiPT) artificial H H2C=CH-CH2 CH(CH3)2 N-allyl-N-isopropyltryptamine
N-DEAOP-NMT artificial H ? CH3 N-(3-diethylamino-3-oxopropyl)-N-methyltryptamine
5-MeO-N-DEAOP-NMT artificial 5-OCH3 ? CH3 N-(3-diethylamino-3-oxopropyl)-N-methyl-5-methoxytryptamine
N-DEAOP-NET[48] artificial H ? CH2CH3 N-(3-diethylamino-3-oxopropyl)-N-ethyltryptamine
5-MeO-N-DEAOP-NET artificial 5-OCH3 ? CH2CH3 N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-methoxytryptamine
1-Methyl-DMT artificial 1-CH3 CH3 CH3 1-methyl-N,N-dimethyltryptamine 13366-47-7
2-Methyl-DMT artificial 2-CH3 CH3 CH3 (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine 1080-95-1
2-Methyl-DET artificial 2-CH3 CH2CH3 CH2CH3 N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine 26628-88-6
2-Methyl-DiPT artificial 2-CH3 CH(CH3)2 CH(CH3)2 2-methyl-N,N-diisopropyltryptamine
2-Methyl-iPALT artificial 2-CH3 CH(CH3)2 H2C=CH-CH2 2-methyl-N-isopropyl-N-allyltryptamine 2915652-49-0
4-Amino-DMT [49] artificial 4-NH2 CH3 CH3 4-amino-N,N-dimethyltryptamine 60331-61-5
4-Methyl-DMT artificial 4-CH3 CH3 CH3 4,N,N-trimethyltryptamine 28289-23-8
4-MeO-DMT artificial 4-OCH3 CH3 CH3 4-methoxy-N,N-dimethyltryptamine 3965-97-7
4-MeO-DET artificial 4-OCH3 CH2CH3 CH2CH3 4-methoxy-N,N-diethyltryptamine
4-MeO-MiPT artificial 4-OCH3 CH3 CH(CH3)2 4-methoxy-N-methyl-N-isopropyltryptamine 96096-53-6
4-MeO-DiPT artificial 4-OCH3 CH(CH3)2 CH(CH3)2 4-methoxy-N,N-diisopropyltryptamine
Deupsilocin (d10-psilocin; likely CYB003) artificial 4-OH CH3 CH3 4-Hydroxy-α,α,β,β-Tetradeutero-N,N-bis(trideuteriomethyl)tryptamine 1435934-64-7
4-AcO-DMT (psilacetin) artificial 4-OCOCH3 CH3 CH3 4-acetoxy-N,N-dimethyltryptamine 92292-84-7
4-PrO-DMT artificial 4-OCOCH2CH3 CH3 CH3 4-propionyloxy-N,N-dimethyltryptamine 1373882-11-1
4-GO-DMT (RE109; FT-109) artificial 4-OCO(CH2)3COOH CH3 CH3 4-glutaryloxy-N,N-dimethyltryptamine
4-HO-MET (metocin) artificial 4-OH CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine 77872-41-4
4-AcO-MET artificial 4-OCOCH3 CH3 CH2CH3 4-acetoxy-N-methyl-N-ethyltryptamine 1445751-40-5
4-PrO-MET artificial 4-OCOCH2CH3 CH3 CH2CH3 4-propionyloxy-N-methyl-N-ethyltryptamine
4-PO-MET artificial 4-OPO3H2 CH3 CH2CH3 4-phosphoryloxy-N-methyl-N-ethyltryptamine
4-HO-DET (ethocin) artificial 4-OH CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine 22204-89-3
4-AcO-DET artificial 4-OCOCH3 CH2CH3 CH2CH3 4-acetoxy-N,N-diethyltryptamine 1135424-15-5
4-PO-DET (ethocybin) artificial 4-OPO3H2 CH2CH3 CH2CH3 4-phosphoryloxy-N,N-diethyltryptamine 60480-02-6
4-HO-EPT artificial 4-OH CH2CH3 CH2CH2CH3 4-hydroxy-N-ethyl-N-propyltryptamine 2595431-59-5
4-AcO-EPT artificial 4-OCOCH3 CH2CH3 CH2CH2CH3 4-acetoxy-N-ethyl-N-propyltryptamine 2750249-90-0
4-PO-EPT artificial 4-OPO3H2 CH2CH3 CH2CH2CH3 4-phosphoryloxy-N-ethyl-N-propyltryptamine
4-AcO-EiPT artificial 4-OCOCH3 CH2CH3 CH(CH3)2 4-acetoxy-N-ethyl-N-isopropyltryptamine
4-HO-MPT artificial 4-OH CH3 CH2CH2CH3 4-hydroxy-N-methyl-N-propyltryptamine 763035-03-6
4-AcO-MPT artificial 4-OCOCH3 CH3 CH2CH2CH3 4-acetoxy-N-methyl-N-propyltryptamine 2173386-55-3
4-HO-MiPT artificial 4-OH CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine 77872-43-6
4-AcO-MiPT artificial 4-OCOCH3 CH3 CH(CH3)2 4-acetoxy-N-methyl-N-isopropyltryptamine 1024612-25-6
4-HO-MALT[50] artificial 4-OH CH3 H2C=CH-CH2 4-hydroxy-N-methyl-N-allyltryptamine
4-AcO-MALT[51] artificial 4-OCOCH3 CH3 H2C=CH-CH2 4-acetoxy-N-Methyl-N-allyltryptamine
4-HO-iPALT artificial 4-OH CH(CH3)2 H2C=CH-CH2 4-hydroxy-N-isopropyl-N-allyltryptamine
4-HO-MBT artificial 4-OH (CH2)3CH3 CH3 4-hydroxy-N-butyl-N-methyltryptamine
4-HO-MsBT artificial 4-OH CH(CH3)CH2CH3 CH3 4-hydroxy-N-sec-butyl-N-methyltryptamine
4-HO-MtBT artificial 4-OH C(CH3)3 CH3 4-hydroxy-N-tert-butyl-N-methyltryptamine
4-HO-EiBT artificial[52] 4-OH CH2CH(CH3)2 CH2CH3 4-hydroxy-N-iso-butyl-N-ethyltryptamine
4-HO-McPT artificial 4-OH C3H5 CH3 4-hydroxy-N-cyclopropyl-N-methyltryptamine 2883663-05-4
4-AcO-McPT artificial 4-OCOCH3 C3H5 CH3 4-acetoxy-N-cyclopropyl-N-methyltryptamine
4-HO-McPeT artificial 4-OH C5H9 CH3 4-hydroxy-N-cyclopentyl-N-methyltryptamine 77872-48-1
4-HO-McPMT [53] artificial 4-OH CH2C3H5 CH3 4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
4-HO-DPT artificial 4-OH CH2CH2CH3 CH2CH2CH3 4-hydroxy-N,N-dipropyltryptamine 63065-88-3
4-AcO-DPT artificial 4-OCOCH3 CH2CH2CH3 CH2CH2CH3 4-acetoxy-N,N-dipropyltryptamine 1445751-75-6
4-HO-PiPT artificial 4-OH CH2CH2CH3 CH(CH3)2 4-hydroxy-N-propyl-N-isopropyltryptamine
4-AcO-PiPT artificial 4-OCOCH3 CH2CH2CH3 CH(CH3)2 4-acetoxy-N-propyl-N-isopropyltryptamine
4-HO-DiPT artificial 4-OH CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine 132328-45-1
4-AcO-DiPT artificial 4-OCOCH3 CH(CH3)2 CH(CH3)2 4-acetoxy-N,N-diisopropyltryptamine 936015-60-0
4-PrO-DiPT artificial 4-OCOCH2CH3 CH(CH3)2 CH(CH3)2 4-propionyloxy-N,N-diisopropyltryptamine 1373882-13-3
Luvesilocin (RE104; FT-104) artificial 4-OCO(CH2)3COOH CH(CH3)2 CH(CH3)2 4-glutaryloxy-N,N-diisopropyltryptamine
4-PO-DiPT artificial 4-OPO3H2 CH(CH3)2 CH(CH3)2 4-phosphoryloxy-N,N-diisopropyltryptamine 1373882-09-7
4-HO-DALT artificial 4-OH H2C=CH-CH2 H2C=CH-CH2 4-hydroxy-N,N-diallyltryptamine 2173386-70-2
4-AcO-DALT artificial 4-OCOCH3 H2C=CH-CH2 H2C=CH-CH2 4-acetoxy-N,N-diallyltryptamine 1445751-71-2
4-HO-DBT artificial 4-OH (CH2)3CH3 (CH2)3CH3 4-hydroxy-N,N-dibutyltryptamine 63065-89-4
4-HO-DiBT artificial 4-OH CH2CH(CH3)2 CH2CH(CH3)2 4-hydroxy-N,N-diisobutyltryptamine
4-HO-DsBT artificial 4-OH CH(CH3)CH2CH3 CH(CH3)CH2CH3 4-hydroxy-N,N-disecbutyltryptamine 127507-01-1
4-Fluoro-DMT artificial 4-F CH3 CH3 4-fluoro-N,N-dimethyltryptamine 1644-64-0
5-MeO-DMT-d4 (α,α,β,β-tetradeutero-5-MeO-DMT) artificial 5-OCH3 CH3 CH3 α,α,β,β-Tetradeutero-5-methoxy-N,N-dimethyltryptamine 66521-37-7
5-MeO-MET artificial 5-OCH3 CH2CH3 CH3 5-methoxy-N-methyl-N-ethyltryptamine 16977-53-0
5-MeO-DET artificial 5-OCH3 CH2CH3 CH2CH3 5-methoxy-N,N-diethyltryptamine 2454-70-8
5-MeO-MPT artificial 5-OCH3 CH3 CH2CH2CH3 5-methoxy-N-methyl-N-propyltryptamine
5-MeO-EPT artificial 5-OCH3 CH2CH3 CH2CH2CH3 5-methoxy-N-ethyl-N-propyltryptamine 850032-67-6
5-MeO-DPT artificial 5-OCH3 CH2CH2CH3 CH2CH2CH3 5-methoxy-N,N-dipropyltryptamine 69496-75-9
5-MeO-MALT artificial 5-OCH3 H2C=CH-CH2 CH3 5-methoxy-N-Methyl-N-allyltryptamine 1373918-64-9
5-MeO-DALT artificial 5-OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine 928822-98-4
ASR-3001 (5-MeO-iPALT) artificial 5-OCH3 H2C=CH-CH2 CH2CH(CH3)2 5-methoxy-N-allyl-N-isopropyltryptamine
5-MeO-MiPT artificial 5-OCH3 CH3 CH(CH3)2 5-methoxy-N,N-methylisopropyltryptamine 96096-55-8
5,6-MeO-MiPT artificial 5-OCH3, 6-OCH3 CH3 CH(CH3)2 5,6-dimethoxy-N,N-methylisopropyltryptamine
5-MeO-MBT artificial 5-OCH3 CH3 (CH2)3CH3 5-methoxy-N-methyl-N-butyltryptamine
5-MeO-MsBT artificial 5-OCH3 CH3 CH(CH3)CH2CH3 5-methoxy-N-methyl-N-sec-butyltryptamine
5-MeO-McPT artificial 5-OCH3 CH3 C3H5 5-methoxy-N-methyl-N-cyclopropyltryptamine
5-MeO-McBT artificial 5-OCH3 CH3 C4H7 5-methoxy-N-methyl-N-cyclobutyltryptamine
5-MeO-EiPT artificial 5-OCH3 CH2CH3 CH(CH3)2 5-methoxy-N-ethyl-N-isopropyltryptamine 850032-66-5
5-MeO-PiPT artificial 5-OCH3 CH2CH2CH3 CH(CH3)2 5-methoxy-N-propyl-N-isopropyltryptamine
5-MeO-DiPT artificial 5-OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine 4021-34-5
5-MeO-DBT artificial 5-OCH3 (CH2)3CH3 (CH2)3CH3 5-methoxy-N,N-dibutyltryptamine 73785-42-9
5-MeO-DsBT artificial 5-OCH3 CH(CH3)CH2CH3 CH(CH3)CH2CH3 5-methoxy-N,N-di-sec-butyltryptamine
5-MeS-DMT artificial 5-SCH3 CH3 CH3 5-methylthio-N,N-dimethyltryptamine 5102-11-4
5-AcO-DMT (O-acetylbufotenine) artificial 5-OCOCH3 CH3 CH3 5-acetoxy-N,N-dimethyltryptamine 16977-50-7
5-t-BuCO-DMT (O-pivalylbufotenine) artificial ? CH3 CH3 5-pivaloxy-N,N-dimethyltryptamine ?
5-AcO-MET [54] artificial 5-OCOCH3 CH3 CH2CH3 5-acetoxy-N-methyl-N-ethyltryptamine
5-AcO-DET artificial 5-OCOCH3 CH2CH3 CH2CH3 5-acetoxy-N,N-diethyltryptamine
5-AcO-EPT [55] artificial 5-OCOCH3 CH2CH3 CH2CH2CH3 5-acetoxy-N-ethyl-N-propyltryptamine
5-AcO-DPT artificial 5-OCOCH3 CH2CH2CH3 CH2CH2CH3 5-acetoxy-N,N-dipropyltryptamine
5-AcO-MiPT artificial 5-OCOCH3 CH3 CH(CH3)2 5-acetoxy-N-methyl-N-isopropyltryptamine
5-AcO-DiPT artificial 5-OCOCH3 CH(CH3)2 CH(CH3)2 5-acetoxy-N,N-diisopropyltryptamine
5-Ethoxy-DMTartificial5-OCH2CH3CH3CH35-ethoxy-N,N-dimethyltryptamine855245-09-9
5-Ethoxy-METartificial5-OCH2CH3CH3CH2CH35-ethoxy-N-methyl-N-ethyltryptamine
5-Ethoxy-DETartificial5-OCH2CH3CH2CH3CH2CH35-ethoxy-N,N-diethyltryptamine
5-Ethoxy-MPTartificial5-OCH2CH3CH3CH2CH2CH35-ethoxy-N-methyl-N-propyltryptamine
5-Ethoxy-EPTartificial5-OCH2CH3CH2CH3CH2CH2CH35-ethoxy-N-ethyl-N-propyltryptamine
5-Ethoxy-DPTartificial5-OCH2CH3CH2CH2CH3CH2CH35-ethoxy-N,N-dipropyltryptamine
5-Ethoxy-MiPTartificial5-OCH2CH3CH3CH(CH3)25-ethoxy-N-methyl-N-isopropyltryptamine
5-Ethoxy-EiPTartificial5-OCH2CH3CH2CH3CH(CH3)25-ethoxy-N-ethyl-N-isopropyltryptamine
5-Ethoxy-DiPTartificial5-OCH2CH3CH(CH3)2CH(CH3)25-ethoxy-N,N-diisopropyltryptamine
5-Ethoxy-DALTartificial5-OCH2CH3H2C=CH-CH2H2C=CH-CH25-ethoxy-N,N-diallyltryptamine
5-BnO-DMT artificial 5-OCH2C6H5 CH3 CH3 5-benzyloxy-N,N-dimethyltryptamine 101832-88-6
5-HO-MET artificial 5-OH CH3 CH2CH3 5-hydroxy-N-methyl-N-ethyltryptamine
5-HO-DET artificial 5-OH CH2CH3 CH2CH3 5-hydroxy-N,N-diethyltryptamine 14009-42-8
5-HO-DPT artificial 5-OH CH2CH2CH3 CH2CH2CH3 5-hydroxy-N,N-dipropyltryptamine 36288-75-2
5-HO-MiPT artificial 5-OH CH3 CH(CH3)2 5-hydroxy-N-methyl-N-isopropyltryptamine
5-HO-DiPT artificial 5-OH CH(CH3)2 CH(CH3)2 5-hydroxy-N,N-diisopropyltryptamine 36288-76-3
5-Methyl-DMT (5,N,N-TMT)artificial5-CH3CH3CH35,N,N-trimethyltryptamine22120-39-4
5-Ethyl-DMTartificial5-CH2CH3CH3CH35-ethyl-N,N-dimethyltryptamine171783-25-8
5-Isopropyl-DMTartificial5-CH(CH3)2CH3CH35-isopropyl-N,N-dimethyltryptamine156281-04-8
5-(t-Butyl)-DMT [56]artificial5-C(CH3)3CH3CH35-(tert-butyl)-N,N-dimethyltryptamine
5-Fluoro-DMTartificial5-FCH3CH35-fluoro-N,N-dimethyltryptamine22120-36-1
Bretisilocin (5-fluoro-MET; GM-2505)artificial5-FCH3CH2CH35-fluoro-N-methyl-N-ethyltryptamine2698331-35-8
5-Fluoro-DETartificial5-FCH2CH3CH2CH35-fluoro-N,N-diethyltryptamine
5-Fluoro-EPTartificial5-FCH2CH3CH2CH2CH35-fluoro-N-ethyl-N-propyltryptamine
5-Fluoro-DPTartificial5-FCH2CH2CH3CH2CH2CH35-fluoro-N,N-dipropyltryptamine
5-Fluoro-PiPTartificial5-FCH2CH2CH3CH(CH3)25-fluoro-N-propyl-N-isopropyltryptamine
5-Fluoro-PcBTartificial5-FCH2CH2CH3CH(CH2)35-fluoro-N-propyl-N-cyclobutyltryptamine
5-Fluoro-iPcBTartificial5-FCH(CH3)2CH(CH2)35-fluoro-N-isopropyl-N-cyclobutyltryptamine
5-Fluoro-DiPTartificial5-FCH(CH3)2CH(CH3)25-fluoro-N,N-diisoproptryptamine
5-Fluoro-sBALTartificial5-FCH(CH3)CH2CH3CH2CH=CH25-fluoro-N-sec-butyl-N-allyltryptamine
5-Fluoro-M1MALTartificial5-FCH3CH(CH3)CH=CH25-fluoro-N-methyl-N-(1-methylallyl)tryptamine
5-Chloro-DMTartificial5-ClCH3CH35-chloro-N,N-dimethyltryptamine22120-32-7
5-Iodo-DMTartificial5-ICH3CH35-iodo-N,N-dimethyltryptamine22120-38-3
5-TFM-DMTartificial5-CF3CH3CH35-(trifluoromethyl)-N,N-dimethyltryptamine2418713-32-1
5-TFMO-DMT[57]artificial5-OCF3CH3CH35-(trifluoromethoxy)-N,N-dimethyltryptamine
5-Nitro-DMT[58]artificial5-NO2CH3CH35-nitro-N,N-dimethyltryptamine69937-13-9
5-CN-DMTartificial5-C≡NCH3CH35-cyano-N,N-dimethyltryptamine17380-42-6
5-CN-DPTartificial5-C≡NCH2CH2CH3CH2CH2CH35-cyano-N,N-dipropyltryptamine74885-19-1
Almotriptan artificial 5-(CH2SO2N(CH2)4) CH3 CH3 N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine 154323-57-6
Rizatriptan artificial 5-(CH2(N3(CH)2)) CH3 CH3 N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine 145202-66-0
Sumatriptan artificial 5-(CH2SO2NHCH3) CH3 CH3 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide 103628-46-2
Zolmitriptan artificial 5-(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine 139264-17-8
6-Fluoro-DMTartificial6-FCH3CH36-fluoro-N,N-dimethyltryptamine1511-31-5
6-Fluoro-DET[59]artificial6-FCH2CH3CH2CH36-fluoro-N,N-diethyltryptamine2836-69-3
6-Chloro-DMTartificial6-ClCH3CH36-chloro-N,N-dimethyltryptamine25390-72-1
6-Methyl-DMTartificial6-CH3CH3CH36,N,N-trimethyltryptamine
6-Hydroxy-DMTartificial6-OHCH3CH36-hydroxy-N,N-dimethyltryptamine1476-33-1
6-Hydroxy-DETartificial6-OHCH3CH36-hydroxy-N,N-diethyltryptamine1476-59-1
6-Methoxy-DMTartificial6-OCH3CH3CH36-methoxy-N,N-dimethyltryptamine2426-88-2
7-Methyl-DMTartificial7-CH3CH3CH37,N,N-trimethyltryptamine65882-39-5
7-Ethyl-DMTartificial7-CH2CH3CH3CH37-ethyl-N,N-dimethyltryptamine
7-Chloro-DMTartificial7-ClCH3CH37-chloro-N,N-dimethyltryptamine
7-Bromo-DMT[60]artificial7-BrCH3CH37-bromo-N,N-dimethyltryptamine74798-68-8
7-Hydroxy-DMTartificial7-OHCH3CH37-hydroxy-N,N-dimethyltryptamine7578-26-9
7-Methoxy-DMTartificial7-OCH3CH3CH37-methoxy-N,N-dimethyltryptamine
7-Methoxy-MiPTartificial7-OCH3CH3CH(CH3)27-methoxy-N-methyl-N-isopropyltryptamine
1-Methylpsilocin artificial 1-CH3, 4-OH CH3 CH3 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole 1465-16-3
1-Methyl-5-MeO-DiPT artificial 1-CH3, 5-OCH3 CH(CH3)2 CH(CH3)2 1-methyl-5-methoxy-N,N-diisopropyltryptamine 1373882-10-0
NBoc-DMT (NB-DMT) artificial 1-OCOC(CH3)3 CH3 CH3 1-(t-butoxycarbonyl)-N,N-dimethyltryptamine
NB-5-MeO-MiPT artificial 1-OCOC(CH3)3, 5-OCH3 CH3 CH(CH3)2 1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
NB-5-MeO-DALT artificial 1-OCOC(CH3)3, 5-OCH3 H2C=CH-CH2 H2C=CH-CH2 1-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine
6-Fluoropsilocinartificial4-OH,6-FCH3CH34-hydroxy-6-fluoro-N,N-dimethyltryptamine312314-12-8
6-Fluoro-5-MeO-DMTartificial5-OCH3,6-FCH3CH35-methoxy-6-fluoro-N,N-dimethyltryptamine
5,6-Difluoro-EPTartificial5-F, 6-FCH2CH3CH2CH2CH35,6-difluoro-N-ethyl-N-propyltryptamine
5-MeO-2-TMT artificial 2-CH3, 5-OCH3 CH3 CH3 2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine 67292-68-6
5-MeO-7-TMT artificial 5-OCH3, 7-CH3 CH3 CH3 5-Methoxy-7,N,N-trimethyltryptamine 61018-77-7
5-MeO-4-TMT artificial 4-CH3, 5-OCH3 CH3 CH3 5-Methoxy-4,N,N-trimethyltryptamine
4-HO-5-MeO-DMT (psilomethoxin) artificial 4-OH, 5-OCH3 CH3 CH3 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine 2433-31-0
4-F-5-MeO-DMT artificial 4-F, 5-OCH3 CH3 CH3 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine 312314-18-4
5-MeO-7-F-MET artificial 5-OCH3, 7-F CH3 CH2CH3 5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
EMDT (2-ethyl-5-MeO-DMT) artificial 2-CH2CH3, 5-OCH3 CH3 CH3 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine 263744-72-5
ST-1936 (2-methyl-5-chloro-DMT) artificial 2-CH3, 5-Cl CH3 CH3 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine 1210-81-7
Benanserin (benzyl antiserotonin; BAS; MC-4788; Sq-4788) artificial 1-CH2C6H5, 2-CH3, 5-OCH3 H H 2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine 441-91-8
O-4310 (1-isopropyl-6-fluoropsilocin) artificial 1-CH(CH3)2, 4-OH, 6-F CH3 CH3 3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol 885671-63-6
CP-132,484 (4,5-DHP-1-Me-T) artificial 1-methyl-4,5-(OCH2CH2CH2) H H 1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole 143508-76-3
4,5-DHP-DMT artificial 4,5-(OCH2CH2CH2) CH3 CH3 1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole 135360-97-3
4,5-DHF-DMT (P-3) artificial[61] 4,5-(CH2CH2O) CH3 CH3 2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
4,5-Methylbenzoxazole-DMT (P-131) artificial 4,5-(OC(CH3)=N) CH3 CH3 N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine
4,5-MDO-DMT artificial 4,5-(OCH2O) CH3 CH3 2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine 81249-30-1
4,5-MDO-DiPT artificial 4,5-(OCH2O) CH(CH3)2 CH(CH3)2 N-[2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine 82173-82-8
5,6-FUR-DMT (P-4) artificial 5,6-(CH=CHO) CH3 CH3 2-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine
5,6-MDO-DMT artificial 5,6-(OCH2O) CH3 CH3 2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine
5,6-MDO-MiPT artificial 5,6-(OCH2O) CH3 CH(CH3)2 N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine
5,6-MDO-DiPT artificial 5,6-(OCH2O) CH(CH3)2 CH(CH3)2 N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine
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List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen.[62][63][64] α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.[64] This is analogous to α-methylation of phenethylamine into amphetamine.[64]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[65][66][67][68] and produce psychostimulant, entactogen, and/or psychedelic effects.[62][63][64] The most well-known of these agents are α-methyltryptamine (AMT) and α-ethyltryptamine (AET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[63][64] In accordance with its action as a dual releasing agent of serotonin and dopamine, AET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as AMT, 5-MeO-AMT, and various others.[69]

More information Structure, Name ...
Structure Name Chemical name CAS #
Tryptophan (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid 73-22-3
5-Hydroxytryptophan (5-HTP) (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid 4350-09-8
5-Methoxytryptophan (5-MTP) (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid 2504-22-5
α-Methyltryptophan (2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid 16709-25-4
α-Methyl-5-HTP (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)-2-methylpropanoic acid 150852-19-0
α-Methyl-5-MTP (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)-2-methylpropanoic acid ?
AMT (αMT; α-MT; Indopan) 1-(1H-Indol-3-yl)propan-2-amine 299-26-3
2,α-DMT (2-methyl-AMT) 1-(2-methyl-1H-indol-3-yl)propan-2-amine 4966-28-3
4-Methyl-AMT 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine 3569-29-7
5-Fluoro-AMT 1-(5-fluoro-1H-indol-3-yl)propan-2-amine 712-08-3
5-Chloro-AMT 1-(5-Chloro-1H-indol-3-yl)propan-2-amine 712-07-2
5-HO-AMT (αMS/α-methyl-5-HT) 3-(2-aminopropyl)-1H-indol-5-ol 304-52-9
5-MeO-AMT 1-(5-methoxy-1H-indol-3-yl)propan-2-amine 1137-04-8
5-Ethoxy-AMT 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine 101832-83-1
5-Isopropoxy-AMT 1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine
5-Allyloxy-AMT 1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine
1-Propyl-5-MeO-AMT 1-(5-methoxy-1-propylindol-3-yl)propan-2-amine ?
BW-723C86 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine 160521-72-2
6-Fluoro-AMT 1-(6-fluoro-1H-indol-3-yl)propan-2-amine 712-11-8
7-Chloro-AMT 1-(7-chloro-1H-indol-3-yl)propan-2-amine 711-99-9
AL-37350A (4,5-DHP-AMT) (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole 362603-40-5
Compound 5 [70] 1-(3H-benzo[e]indol-1-yl)propan-2-amine
AET (αET; α-ET) 1-(1H-indol-3-yl)butan-2-amine 2235-90-7
4-Methyl-AET 1-(4-Methyl-1H-indol-3-yl)butan-2-amine 28289-30-7
4-HO-AET 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine 28289-28-3
5-Fluoro-AET 1-(5-fluoro-1H-indol-3-yl)butan-2-amine 1380137-98-3
5-Chloro-AET 1-(5-chloro-1H-indol-3-yl)butan-2-amine ?
5-Methyl-AET 1-(5-methyl-1H-indol-3-yl)butan-2-amine 1380148-21-9
5-MeO-AET 1-(5-methoxy-1H-indol-3-yl)butan-2-amine 4765-10-0
7-Methyl-AET 1-(7-methyl-1H-indol-3-yl)butan-2-amine 13712-80-6
α,N-DMT (SK&F-7024, Ro 3-1715; N-methyl-AMT) 1-(1H-indol-3-yl)-N-methylpropan-2-amine 299-24-1
N,N-Dimethyl-AMT (α,N,N-TMT) (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine 4761-32-4
N-Hydroxy-AMT (N-HO-AMT) N-[1-(1H-indol-3-yl)propan-2-yl]hydroxylamine 63-33-2
N-Methyl-5-MeO-AMT (α,N,O-TMS/α,N,O-trimethyl-5-HT) [1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine 4822-13-3
N,N-Dimethyl-5-MeO-AMT (5-MeO-α,N,N-TMT) (2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine 101831-90-7
α-Propyltryptamine (APT; αPT; α-PT) 1-(1H-indol-3-yl)pentan-2-amine
Indolylpropylaminopentane (IPAP; α,N-DPT) 1-(1H-indol-3-yl)-N-propylpentan-2-amine
α-Methyl-DiPT (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
MPMI[71] 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole 143321-54-4
Lucigenol (4-HO-MPMI) 3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole ?
5-MeO-MPMI (CP-108509) 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole 143321-57-7
5-Fluoro-MPMI[72] 5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole ?
5-Bromo-MPMI 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole 143322-57-0
Eletriptan 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole 143322-58-1
Z5247692566[45][73] 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine
BK-NM-AMT (α,N-dimethyl-β-ketotryptamine)[74][75][76] 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine)[77][78][79][76] 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[79][80][81] 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine)[79][82][83] 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one
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List of substituted β-ketotryptamines

A number of β-ketotryptamines (beta-ketotryptamines) are known.[74][76][79] These compounds are α-alkyl-β-ketotryptamines and are analogous to the cathinones (β-ketoamphetamines) of the related phenethylamine family. Known β-ketotryptamines include BK-NM-AMT, BK-5F-NM-AMT, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT.[74][76][79] They act as monoamine releasing agents.[74][76][79]

Cyclized tryptamines

Examples of cyclized tryptamines include:

Other closely related cyclized tryptamine-like compounds include the following:

Related compounds

A number of related compounds are known, with a similar structure but having the indole core flipped (isotryptamines) and/or replaced with related cores such as indene, indoline, indazole, indolizine, benzothiophene, or benzofuran. Like tryptamines, these related compounds are primarily active as agonists at the 5-HT2 family of serotonin receptors, with applications in the treatment of glaucoma, cluster headaches, or as anorectics.

More information Structure, Name ...
Structure Name Chemical name CAS #
C-DMT (1-carba-DMT) 2-(3H-inden-1-yl)-N,N-dimethylethanamine
O-DMT (1-oxa-DMT, DMBF) 2-(1-benzofuran-3-yl)-N,N-dimethylethanamine
MiPBF (1-oxa-MiPT) N-[2-(1-benzofuran-3-yl)ethyl]-N-methylpropan-2-amine
Dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine 140853-58-3
5-MeO-DiBF (1-oxa-5-MeO-DiPT) N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
3-APB (1-oxa-AMT) 3-(2-aminopropyl)benzofuran 105909-13-5
Mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) 3-(2-aminopropyl)-5-methoxybenzofuran 140853-59-4
S-DMT (1-thia-DMT) 2-(1-benzothiophen-3-yl)-N,N-dimethylethanamine 10275-64-6
3-APBT (SKF-6678; 1-thia-AMT) 1-(1-benzothiophen-3-yl)propan-2-amine 1201-27-0
Isotryptamine (isoT) 2-indol-1-ylethanamine 13708-58-2
isoAMT 1-indol-1-ylpropan-2-amine 1227465-67-9
(S)-5,6-Difluoro-isoAMT [84] (S)-1-(5,6-difluoroindol-1-yl)propan-2-amine
Ro60-0175 ((S)-5-F-6-Cl-isoAMT) (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine 169675-09-6
isoDMT 2-indol-1-yl-N,N-dimethylethanamine 87482-09-5
5-MeO-isoDMT 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine 244122-80-3
6-MeO-isoDMT 2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine 87482-11-9
Zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-Me-isoDMT) (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine 2481740-94-5
2ZEDMA 2-indolizin-1-yl-N,N-dimethylethanamine
1ZP2MA 1-indolizin-1-yl-N-methylpropan-2-amine
1Z2MAP1O 1-indolizin-3-yl-2-(methylamino)propan-1-one 2110204-31-2
Example 16 [85][86] 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
Example 1 [87] 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine
VER-3323 (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine 259857-99-3
AL-34662 (indazole-5-HO-AMT) 1-((S)-2-Aminopropyl)-1H-indazol-6-ol 210580-75-9
O-Methyl-AL-34662 (indazole-5-MeO-AMT) 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole 210580-60-2
7-Methyl-AL-34662 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol 874668-67-4
7-Chloro-AL-34662 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol 874881-86-4
AL-38022A (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine 478132-11-5
Example 9 [88] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine 478132-12-6
Example 3 [89] (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine 890087-75-9
Example 1 [90] (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine 1373917-69-1
YM-348 (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine 372163-84-3
2-Desethyl-YM-348 [91] (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine 748116-94-1
I-32 [92] 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
2-Azapsilocin (Psilocin indazole analogue, P-6)[93] 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol
4-Aza-5-MeO-DPT (P-11) N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine
5-Aza-4-MeO-DiPT (P-36) N-[2-(4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
7-Aza-5-MeO-DiPT (P-19) N-[2-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
RS134-49 (4-Me-THPI) 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole 2945139-94-4
RU-28253 (5-MeO-THPI) 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole ?
NEtPhOH-THPI (compound 24c) 3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole ?
VU6067416[94] 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole 3027515-24-5
(R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine 2765652-48-8
(R)-70 3-[(3R)-1,3-dimethyl-3,6-dihydro-2H-pyridin-5-yl]-1H-pyrrolo[2,3-b]pyridine ?
SN-22 3-(1-methylpiperidin-4-yl)-1H-indole 17403-07-5
RU-24,969 5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole 107008-28-6
EMD-386088 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole 54635-62-0
T-70[95] N,N-dimethyl-2-(6H-thieno[2,3-b]pyrrol-4-yl)ethan-1-amine ?
T-72[96] N,N-dimethyl-2-(4H-thieno[3,2-b]pyrrol-6-yl)ethan-1-amine ?
Gramine 1-(1H-indol-3-yl)-N,N-dimethylmethanamine 87-52-5
Homotryptamine 3-(1H-indol-3-yl)propan-1-amine 6245-89-2
Dimethylhomotryptamine (DMHT) 3-(1H-indol-3-yl)-N,N-dimethylpropan-1-amine 13117-35-6
Indalpine 3-(2-piperidin-4-ylethyl)-1H-indole 63758-79-2
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Overview table

More information Simple, 4-Hydroxy ...
Simple tryptamines and their common derivatives
Simple4-Hydroxy4-Acetoxy5-Methoxy5-Hydroxy
Tryptamine (T)4-HO-T (dinorpsilocin)4-AcO-T5-MeO-T (O-methylserotonin)5-HO-T (serotonin; 5-HT)
NAcT4-HO-NAcT4-AcO-NAcT5-MeO-NAcT (melatonin)5-HO-NAcT (normelatonin; NAS)
NMT4-HO-NMT (norpsilocin)4-AcO-NMT5-MeO-NMT5-HO-NMT (N-methylserotonin)
NET4-HO-NET4-AcO-NET5-MeO-NET5-HO-NET
NPT4-HO-NPT4-AcO-NPT5-MeO-NPT5-HO-NPT
NiPT4-HO-NiPT4-AcO-NiPT5-MeO-NiPT5-HO-NiPT
NALT4-HO-NALT4-AcO-NALT5-MeO-NALT5-HO-NALT
NBT (NnBT)4-HO-NBT4-AcO-NBT5-MeO-NBT5-HO-NBT
NiBT4-HO-NiBT4-AcO-NiBT5-MeO-NiBT5-HO-NiBT
NsBT4-HO-NsBT4-AcO-NsBT5-MeO-NsBT5-HO-NsBT
NtBT4-HO-NtBT4-AcO-NtBT5-MeO-NtBT5-HO-NtBT
NAT4-HO-NAT4-AcO-NAT5-MeO-NAT5-HO-NAT
NHT4-HO-NHT4-AcO-NHT5-MeO-NHT5-HO-NHT
NcPT4-HO-NcPT4-AcO-NcPT5-MeO-NcPT5-HO-NcPT
NcHT4-HO-NcHT4-AcO-NcHT5-MeO-NcHT5-HO-NcHT
NBnT4-HO-NBnT4-AcO-NBnT5-MeO-NBnT5-HO-NBnT
NBOMeT4-HO-NBOMeT4-AcO-NBOMeT5-MeO-NBOMeT5-HO-NBOMeT
NB3OMeT4-HO-NB3OMeT4-AcO-NB3OMeT5-MeO-NB3OMeT5-HO-NB3OMeT
DMT4-HO-DMT (psilocin)4-AcO-DMT (psilacetin)5-MeO-DMT (mebufotenin)5-HO-DMT (bufotenin)
DET4-HO-DET (ethocin)4-AcO-DET (ethacetin)5-MeO-DET5-HO-DET
DPT4-HO-DPT (deprocin)4-AcO-DPT (depracetin)5-MeO-DPT5-HO-DPT (DiPS, NDPS)
DiPT4-HO-DiPT (iprocin)4-AcO-DiPT (ipracetin)5-MeO-DiPT (foxy)5-HO-DiPT
DALT4-HO-DALT (daltocin)4-AcO-DALT (dalcetin)5-MeO-DALT (foxtrot)5-HO-DALT
DBT4-HO-DBT4-AcO-DBT5-MeO-DBT5-HO-DBT
DiBT4-HO-DiBT4-AcO-DiBT5-MeO-DiBT5-HO-DiBT
DsBT4-HO-DsBT4-AcO-DsBT5-MeO-DsBT5-HO-DsBT
DtBT4-HO-DtBT4-AcO-DtBT5-MeO-DtBT5-HO-DtBT
DAT4-HO-DAT4-AcO-DAT5-MeO-DAT5-HO-DAT
DHT4-HO-DHT4-AcO-DHT5-MeO-DHT5-HO-DHT
DcPT4-HO-DcPT4-AcO-DcPT5-MeO-DcPT5-HO-DcPT
MET4-HO-MET (metocin)4-AcO-MET (metacetin)5-MeO-MET5-HO-MET
MPT4-HO-MPT (meprocin)4-AcO-MPT5-MeO-MPT5-HO-MPT
MiPT4-HO-MiPT (miprocin)4-AcO-MiPT (mipracetin)5-MeO-MiPT (moxy)5-HO-MiPT
MALT4-HO-MALT (maltocin)4-AcO-MALT5-MeO-MALT5-HO-MALT
MBT4-HO-MBT4-AcO-MBT5-MeO-MBT5-HO-MBT
MiBT4-HO-MiBT4-AcO-MiBT5-MeO-MiBT5-HO-MiBT
MsBT4-HO-MsBT4-AcO-MsBT5-MeO-MsBT5-HO-MsBT
MtBT4-HO-MtBT4-AcO-MtBT5-MeO-MtBT5-HO-MtBT
McPT4-HO-McPT4-AcO-McPT5-MeO-McPT5-HO-McPT
McPMT4-HO-McPMT4-AcO-McPMT5-MeO-McPMT5-HO-McPMT
McPeT4-HO-McPeT4-AcO-McPeT5-MeO-McPeT5-HO-McPeT
EPT4-HO-EPT (eprocin)4-AcO-EPT5-MeO-EPT5-HO-EPT
EiPT4-HO-EiPT (eiprocin)4-AcO-EiPT (ethipracetin)5-MeO-EiPT5-HO-EiPT
EALT4-HO-EALT4-AcO-EALT5-MeO-EALT5-HO-EALT
EBT4-HO-EBT4-AcO-EBT5-MeO-EBT5-HO-EBT
EiBT4-HO-EiBT (eibucin)4-AcO-EiBT5-MeO-EiBT5-HO-EiBT
EsBT4-HO-EsBT4-AcO-EsBT5-MeO-EsBT5-HO-EsBT
EtBT4-HO-EtBT4-AcO-EtBT5-MeO-EtBT5-HO-EtBT
EcPT4-HO-EcPT4-AcO-EcPT5-MeO-EcPT5-HO-EcPT
PiPT4-HO-PiPT (piprocin)4-AcO-PiPT5-MeO-PiPT5-HO-PiPT
PALT4-HO-PALT4-AcO-PALT5-MeO-PALT5-HO-PALT
PBT4-HO-PBT4-AcO-PBT5-MeO-PBT5-HO-PBT
PiBT4-HO-PiBT4-AcO-PiBT5-MeO-PiBT5-HO-PiBT
PsBT4-HO-PsBT4-AcO-PsBT5-MeO-PsBT5-HO-PsBT
PtBT4-HO-PtBT4-AcO-PtBT5-MeO-PtBT5-HO-PtBT
PcPT4-HO-PcPT4-AcO-PcPT5-MeO-PcPT5-HO-PcPT
iPALT (ALiPT)4-HO-iPALT4-AcO-iPALT5-MeO-iPALT (ASR-3001)5-HO-iPALT
iPBT (BiPT)4-HO-iPBT4-AcO-iPBT5-MeO-iPBT5-HO-iPBT
iPiBT4-HO-iPiBT4-AcO-iPiBT5-MeO-iPiBT5-HO-iPiBT
iPsBT4-HO-iPsBT4-AcO-iPsBT5-MeO-iPsBT5-HO-iPsBT
iPtBT4-HO-iPtBT4-AcO-iPtBT5-MeO-iPtBT5-HO-iPtBT
iPcPT4-HO-iPcPT4-AcO-iPcPT5-MeO-iPcPT5-HO-iPcPT
TMT4-HO-TMT4-AcO-TMT5-MeO-TMT5-HO-TMT
Pyr-T4-HO-pyr-T4-AcO-pyr-T5-MeO-pyr-T5-HO-pyr-T
Pip-T4-HO-pip-T4-AcO-pip-T5-MeO-pip-T5-HO-pip-T
Mor-T4-HO-mor-T4-AcO-mor-T5-MeO-mor-T5-HO-mor-T
MPMI4-HO-MPMI (lucigenol)4-AcO-MPMI5-MeO-MPMI (CP-108509)5-HO-MPMI
THPI4-HO-THPI4-AcO-THPI5-MeO-THPI (RU-28253)5-HO-THPI
IsoqT4-HO-IsoqT4-AcO-IsoqT5-MeO-IsoqT5-HO-IsoqT
N-DEAOP-NMT4-HO-N-DEAOP-NMT4-AcO-N-DEAOP-NMT5-MeO-N-DEAOP-NMT5-HO-N-DEAOP-NMT
N-DEAOP-NET4-HO-N-DEAOP-NET4-AcO-N-DEAOP-NET5-MeO-N-DEAOP-NET5-HO-N-DEAOP-NET
Notes: (1) Other notable acyloxy derivatives of the above include 4-PrO-DMT, 4-PrO-DiPT, 4-PrO-MET, 4-GO-DMT, and 4-GO-DiPT (luvesilocin). (2) 4-Phosphoroxy derivatives of the above include norbaeocystin (4-PO-T), baeocystin (4-PO-NMT), psilocybin (4-PO-DMT), ethocybin (4-PO-DET), 4-PO-DiPT, 4-PO-MET, and aeruginascin (4-PO-TMT). (3) α-Alkyl derivatives of the above are as follows: Tryptamine: AMT, AET, 4-HO-AMT, 4-HO-AET, 5-MeO-AMT, 5-MeO-AET, and 5-HO-AMT (α-methylserotonin); NMT: α,N-DMT and α,N,O-TMS; NPT: IPAP (α,N-DPT); DMT: α,N,N-TMT and α,N,N,O-TeMS; and no others for the rest.
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