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Substituted tryptamine
Class of indoles From Wikipedia, the free encyclopedia
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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.
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]
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Use and effects
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Perspective
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 ...
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| Tryptamine (T) | Tryptamine | >100 mga | – | |
| NMT | N-Methyltryptamine | Unknownb | – | |
| NET | N-Ethyltryptamine | Unknown | Unknown | |
| NiPT | N-Isopropyltryptamine | Unknown | Unknown | |
| NsBT | N-sec-Butyltryptamine | 25–75 mg | "Short" | |
| NtBT | N-tert-Butyltryptamine | 5–20 mg | Unknown | |
| NAT | N-Amyltryptamine | >100 mg | – | |
| NHT | N-Hexyltryptamine | >100 mg | – | |
| DMT | N,N-Dimethyltryptamine | >350–1,000 mgc | – | |
| DET | N,N-Diethyltryptamine | 50–150 mg | 2–4 hours | |
| DPT | N,N-Dipropyltryptamine | 100–250 mg | 2–4 hours | |
| DiPT | N,N-Diisopropyltryptamine | 25–100 mg (15–150 mg+) | 4–8 hours | |
| DALT | N,N-Diallyltryptamine | 60–80 mg | <3 hours | |
| DBT | N,N-Dibutyltryptamine | ≥100 mg | Unknown | |
| DAT | N,N-Diamyltryptamine | Unknown | Unknown | |
| DHT | N,N-Dihexyltryptamine | >100 mg | – | |
| MET | N-Methyl-N-ethyltryptamine | 80–100 mg | Unknown | |
| MPT | N-Methyl-N-propyltryptamine | >50 mg | Unknown | |
| MiPT | N-Methyl-N-isopropyltryptamine | 10–25 mg | 3–4 hours | |
| MALT | N-Methyl-N-allyltryptamine | 25–50 mg | Unknown | |
| MBT | N-Methyl-N-butyltryptamine | 250–400 mg | 4–6 hours | |
| MsBT | N-Methyl-N-sec-butyltryptamine | 250–400 mg | Unknown | |
| EPT | N-Ethyl-N-propyltryptamine | Unknown | Unknown | |
| EiPT | N-Ethyl-N-isopropyltryptamine | 24–40 mg | 4–6 hours | |
| PiPT | N-Propyl-N-isopropyltryptamine | Unknown | Unknown | |
| Pyr-T | N,N-Tetramethylenetryptamine | Unknown | Unknown | |
| Pip-T | N,N-Pentamethylenetryptamine | Unknown | Unknown | |
| Mor-T | 3-(2-Morpholinoethyl)indole | Unknownd | Unknown | |
| 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 ...
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| 4-HT (4-HO-T) | 4-Hydroxytryptamine | Unknown | Unknown | |
| Norbaeocystin (4-PO-T) | 4-Phosphoryloxytryptamine | Unknown | Unknown | |
| Norpsilocin (4-HO-NMT) | 4-Hydroxy-N-methyltryptamine | Unknown | Unknown | |
| Baeocystin (4-PO-NMT) | 4-Phosphoryloxy-N-methyltryptamine | 4–10 mga | Unknown | |
| Psilocin (4-HO-DMT) | 4-Hydroxy-N,N-dimethyltryptamine | 10–20 mg (5–40 mg+) | 3–6 hours | |
| Psilocybin (4-PO-DMT) | 4-Phosphoryloxy-N,N-dimethyltryptamine | 10–20 mg (5–40 mg+) | 3–6 hours | |
| 4-AcO-DMT (psilacetin) | 4-Acetoxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 4-PrO-DMT | 4-Propionyloxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 4-HO-DET (ethocin) | 4-Hydroxy-N,N-diethyltryptamine | 10–25 mg | 4–6 hours | |
| Ethocybin (4-PO-DET) | 4-Phosphoryloxy-N,N-diethyltryptamine | 15–30 mg | 4–6 hours | |
| 4-HO-DPT (deprocin) | 4-Hydroxy-N,N-dipropyltryptamine | >20 mg | 5–8 hours | |
| 4-HO-DiPT (iprocin) | 4-Hydroxy-N,N-diisopropyltryptamine | 12–20 mg (3–30 mg+) | 2–3 hours | |
| 4-AcO-DiPT (ipracetin) | 4-Acetoxy-N,N-diisopropyltryptamine | 6–10 mg | Unknown | |
| Luvesilocin (4-GO-DiPT) | 4-Glutaryloxy-N,N-diisopropyltryptamine | Unknownb | Unknownb | |
| 4-HO-DALT (daltocin) | 4-Hydroxy-N,N-diallyltryptamine | Unknown | Unknown | |
| 4-HO-DBT | 4-Hydroxy-N,N-dibutyltryptamine | >20 mg | Unknown | |
| 4-HO-DiBT | 4-Hydroxy-N,N-diisobutyltryptamine | >20 mg | Unknown | |
| 4-HO-DtBT | 4-HydroxyN,N-di-tert-butyltryptamine | Unknown | Unknown | |
| 4-HO-MET (metocin) | 4-Hydroxy-N-methyl-N-ethyltryptamine | 10–20 mg (2–45 mg+) | 4–6 hours | |
| 4-HO-MPT (meprocin) | 4-Hydroxy-N-methyl-N-propyltryptamine | 8–30 mg | Unknown | |
| 4-HO-MiPT (miprocin) | 4-Hydroxy-N-methyl-N-isopropyltryptamine | 12–25 mg (6–30 mg) | 4–6 hours | |
| 4-HO-MALT (maltocin) | 4-Hydorxy-N-methyl-N-allyltryptamine | Unknown | Unknown | |
| 4-HO-MtBT | 4-Hydroxy-N-methyl-N-tert-butyltryptamine | >15 mg | Unknown | |
| 4-HO-EPT (eprocin) | 4-Hydroxy-N-ethyl-N-propyltryptamine | Unknown | Unknown | |
| 4-HO-EiPT | 4-Hydroxy-N-ethyl-N-isopropyltryptamine | Unknown | Unknown | |
| 4-HO-PiPT (piprocin) | 4-Hydroxy-N-propyl-N-isopropyltryptamine | Unknown | Unknown | |
| 4-HO-TMT | 4-Hydroxy-N,N,N-trimethyltryptamine | Unknown | Unknown | |
| Aeruginascin (4-PO-TMT) | 4-Phosphoryloxy-N,N,N-trimethyltryptamine | Unknown | Unknown | |
| 4-HO-pyr-T | 4-Hydroxy-N,N-tetramethylenetryptamine | >20 mg | Unknown | |
| 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] Individual: [14][15][24][25] | ||||
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5-Hydroxytryptamines
More information Compound, Chemical name ...
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| Serotonin (5-HT, 5-HO-T) | 5-Hydroxytryptamine | >100 mga | – | |
| N-Methylserotonin (norbufotenin; 5-HO-NMT) | 5-Hydroxy-N-methyltryptamine | Unknown | Unknown | |
| Bufotenin (5-HO-DMT) | 5-Hydroxy-N,N-dimethyltryptamine | >100 mgb | – | |
| O-Acetylbufotenin (5-AcO-DMT) | 5-Acetoxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| O-Pivalylbufotenin (5-t-BuCO-DMT) | 5-Pivaloxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 5-HO-DET | 5-Hydroxy-N,N-diethyltryptamine | Unknown | Unknown | |
| 5-HO-DPT (DiPS, NDPS) | 5-Hydroxy-N,N-dipropyltryptamine | Unknown | Unknown | |
| 5-HO-DiPT | 5-Hydroxy-N,N-diisopropyltryptamine | Unknown | Unknown | |
| 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: [26][27][28][29] | ||||
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5-Methoxytryptamines
More information Compound, Chemical name ...
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| 5-MT (5-MeO-T) | 5-Methoxytryptamine | Unknown | Unknown | |
| 5-MeO-NMT | 5-Methoxy-N-methyltryptamine | Unknown | Unknown | |
| 5-MeO-NET | 5-Methoxy-N-ethyltryptamine | Unknown | Unknown | |
| 5-MeO-NiPT | 5-Methoxy-N-isopropyltryptamine | Unknown | Unknown | |
| 5-MeO-DMT (mebufotenin) | 5-Methoxy-N,N-dimethyltryptamine | >35 mga | – | |
| 5-MeO-DET | 5-Methoxy-N,N-diethyltryptamine | 1–3 mg | 3–4 hours | |
| 5-MeO-DPT | 5-Methoxy-N,N-dipropyltryptamine | 6–10 mg | 2–4 hours | |
| 5-MeO-DiPT | 5-Methoxy-N,N-diisopropyltryptamine | 6–12 mg | 4–8 hours | |
| 5-MeO-DALT | 5-Methoxy-N,N-diallyltryptamine | 12–25 mg | 2–4 hours | |
| 5-MeO-DBT | 5-Methoxy-N,N-dibutyltryptamine | Unknown | Unknown | |
| 5-MeO-DsBT | 5-Methoxy-N,N-di-sec-butyltryptamine | Unknown | Unknown | |
| 5-MeO-MET | 5-Methoxy-N-methyl-N-ethyltryptamine | Unknown | Unknown | |
| 5-MeO-MPT | 5-Methoxy-N-methyl-N-propyltryptamine | Unknown | Unknown | |
| 5-MeO-MiPT | 5-Methoxy-N-methyl-N-isopropyltryptamine | 4–6 mg (0.5–20 mg+) | 4–6 hours | |
| 5-MeO-MALT | 5-Methoxy-N-methyl-N-allyltryptamine | Unknown | Unknown | |
| 5-MeO-EPT | 5-Methoxy-N-ethyl-N-propyltryptamine | Unknown | Unknown | |
| 5-MeO-EiPT | 5-Methoxy-N-ethyl-N-isopropyltryptamine | Unknown | Unknown | |
| 5-MeO-PiPT | 5-Methoxy-N-propyl-N-isopropyltryptamine | Unknown | Unknown | |
| 5-MeO-iPALT (ASR-3001) | 5-Methoxy-N-isopropyl-N-allyltryptamine | 8–14 mg | 1.5–2.5 hours | |
| 5-MeO-pyr-T | 5-Methoxy-N,N-tetramethylenetryptamine | 0.5–2 mg | Several hours | |
| Melatonin (5-MeO-NAcT) | 5-Methoxy-N-acetyltryptamine | 1–10 mgb | A 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] | ||||
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α-Alkyltryptamines
More information Compound, Chemical name ...
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| AMT (α-methyl-T; Indopan)a | α-Methyltryptamine | 15–40 mg | 12–16 hours | |
| AET (α-ethyl-T; etryptamine; Monase)b | α-Ethyltryptamine | 100–160 mg | 6–8 hours | |
| α,N-DMT (N-methyl-AMT)c | α-Methyl-N-methyltryptamine | 50–100 mg | 6–8 hours | |
| α,N,N-TMT (N,N-dimethyl-AMT) | α,N,N-Trimethyltryptamine | Unknownd | Unknown | |
| 2,α-DMT (2-methyl-AMT) | 2-Methyl-α-methyltryptamine | 300–500 mg | 7–10 hours | |
| 4-HO-AMT (MP-14) | 4-Hydroxy-α-methyltryptamine | 15–20 mg+ | Unknown | |
| 4-Methyl-AMT (MP-809) | 4-Methyl-α-methyltryptamine | 20–60 mg+ | Unknown | |
| 5-Fluoro-AMT (PAL-212, PAL-544) | 5-Fluoro-α-methyltryptamine | 25 mg+ | >9 hours | |
| 5-Chloro-AMT (PAL-542) | 5-Chloro-α-methyltryptamine | Unknown | Unknown | |
| 5-Fluoro-AET (PAL-545) | 5-Fluoro-α-ethyltryptamine | Unknown | Unknown | |
| 5-Chloro-AET (PAL-526) | 5-Chloro-α-ethyltryptamine | Unknown | Unknown | |
| 6-Fluoro-AMT | 6-Fluoro-α-methyltryptamine | 25–75 mg | "Long" | |
| α-Methylserotonin (AMS; 5-HO-AMT) | α-Methyl-5-hydroxytryptamine | Unknown | Unknown | |
| α,O-DMS (5-MeO-AMT) | α-Methyl-5-methoxytryptamine | 2.5–5 mg (0.5–15 mg) | 12–18 hours | |
| α,N,O-TMS (5-MeO-N-methyl-AMT) | α-Methyl-5-methoxy-N-methyltryptamine | 10–20 mg | 6–8 hours | |
| α,N,N,O-TeMS (5-MeO-N,N-dimethyl-AMT) | 5-Methoxy-α,N,N-trimethyltryptamine | Unknown | Unknown | |
| 5-MeO-AET | α-Ethyl-5-methoxytryptamine | ~70 mg | Several hours | |
| Bk-NM-AMT (β-keto-N-methyl-AMT)e | α-Methyl-β-keto-N-methyltryptamine | Unknown | Unknown | |
| 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: [30][31] | ||||
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Other tryptamines
More information Compound, Chemical name ...
| Compound | Chemical name | Dose | Duration | |
|---|---|---|---|---|
| 2-Methyl-DMT | 2-Methyl-N,N-dimethyltryptamine | 50–100 mg | 4–6 hours | |
| 2-Methyl-DET | 2-Methyl-N,N-diethyltryptamine | 80–120 mg | 6–8 hours | |
| 4-MeO-DMT | 4-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 4-MeO-DET | 4-Methoxy-N,N-diethyltryptamine | >30 mg | Unknown | |
| 4-MeO-DiPT | 4-Methoxy-N,N-diisopropyltryptamine | Unknown | Unknown | |
| 4-MeO-MiPT | 4-Methoxy-N-methyl-N-isopropyltryptamines | 20–30 mg | 4–6 hours | |
| 4,5-MDO-DMT | 4,5-Methylenedioxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 4,5-MDO-DiPT | 4,5-Methylenedioxy-N,N-diisopropyltryptamine | >25 mg | Unknown | |
| 5-Fluoro-DMT | 5-Fluoro-N,N-dimethyltryptamine | Unknown | Unknown | |
| 5-Chloro-DMT | 5-Chloro-N,N-dimethyltryptamine | Unknown | Unknown | |
| 5-Bromo-DMT | 5-Bromo-N,N-dimethyltryptamine | Unknowna | Unknown | |
| Bretisilocin (5-fluoro-MET) | 5-Fluoro-N-methyl-N-ethyltryptamine | Unknownb | Unknownb | |
| 5-MeO-2-TMT | 5-Methoxy-2-methyl-N,N-dimethyltryptamine | 75–150 mg | 5–10 hours | |
| 5-MeS-DMT | 5-Methylthio-N,N-dimethyltryptamine | Unknownc | Unknownc | |
| 5,6-MeO-MiPT | 5,6-Dimethoxy-N-methyl-N-isopropyltryptamine | >75 mg | Unknown | |
| 5,6-MDO-DMT | 5,6-Methylenedioxy-N,N-dimethyltryptamine | >5 mg | Unknown | |
| 5,6-MDO-DiPT | 5,6-Methylenedioxy-N,N-diisopropyltryptamine | Unknown | Unknown | |
| 5,6-MDO-MiPT | 5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine | >50–60 mg | Unknown | |
| 6-Fluoro-DMT | 6-Fluoro-N,N-dimethyltryptamine | Unknown | Unknown | |
| 6-Fluoro-DET | 6-Fluoro-N,N-diethyltryptamine | >80 mg | Unknown | |
| 6-HO-DMT | 6-Hydroxy-N,N-dimethyltryptamine | >80 mg | Unknown | |
| 6-HO-DET | 6-Hydroxy-N,N-diethyltryptamine | ≥10 mgd | 3–4 hoursd | |
| 6-MeO-DMT | 6-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 6-MeO-DiPT | 6-Methoxy-N,N-diisopropyltryptamine | >50 mg | Unknown | |
| 6-MeO-MiPT | 6-Methoxy-N-methyl-N-isopropyltryptamine | >50 mg | Unknown | |
| 7-MeO-DMT | 7-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown | |
| 7-MeO-DiPT | 7-Methoxy-N,N-diisopropyltryptamine | >70 mg | Unknown | |
| 7-MeO-MiPT | 7-Methoxy-N-methyl-N-isopropyltryptamine | >70 mg | Unknown | |
| 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: [32][33][21] | ||||
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Interactions
Pharmacology
Pharmacodynamics
More information Compound, 5-HT1A ...
| Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 | SERT |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| DMT | 269 | 447 | 117 | 380 | 380 | 112 | 257 | – | 2,090 | 275 | 69 | 2,400 |
| Psilocin | 372 | 191 | 98 | 339 | 200 | 25 | 245 | – | 447 | 79 | 87 | 2,570 |
| Psilocybin | 5,250 | – | 195 | – | 851 | 479 | 3,090 | – | – | 776 | – | – |
| 4-AcO-MALT | 977 | – | 871 | 417 | 692 | 25 | 631 | – | – | 661 | 794 | 3,090 |
| Bufotenin | 8.3 | 59 | 22 | 25 | 224 | 6.2 | 209 | 166 | 302 | 18 | 8.9 | 1,120 |
| 5-MeO-DMT | 10 | 91 | 21 | 575 | 200 | 15 | 490 | – | 589 | 25 | 4.4 | – |
| 5-MeO-DiPT | 170 | – | 871 | – | 324 | 46 | – | – | – | 2,190 | – | – |
| 5-MeO-DALT | 17 | 1,020 | 54 | 977 | 457 | 100 | 2,240 | – | – | 162 | 60 | 4,470 |
| 5-MeO-EiPT | 54 | 1,170 | 174 | – | 1,622 | 98 | – | – | – | 407 | 661 | 5,620 |
| LSD | 5.9 | 21 | 3.5 | 135 | 8.5 | 5.5 | 17 | – | 1.8 | 16 | 8.5 | – |
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More information Compound, 5-HT1A ...
| Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 | SERT |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| DMT | >10,000 | >10,000 | 93 | 456 | 2,323 | 108 | 335 | >10,000 | 611 | 487 | 883 | 3,742 |
| DPT | 32 | 854 | 619 | 2,338 | 2,579 | 42 | 1,567 | >10,000 | 4,373 | 4,543 | 284 | 157 |
| DiPT | 121 | >10,000 | 3,742 | >10,000 | >10,000 | 399 | >10,000 | >10,000 | >10,000 | >10,000 | 3,423 | 1,258 |
| Psilocin | 63 | 305 | 19 | 44 | 340 | 4.7 | 141 | >10,000 | 70 | 72 | 72 | 852 |
| 5-MeO-DMT | 1.9 | 74 | 6.3 | 360 | 2,011 | 3,884 | 538 | >10,000 | 277 | 36 | 3.9 | 2,032 |
| 5-MeO-DiPT | 132 | 5,137 | 1,718 | >10,000 | >10,000 | 163 | >10,000 | >10,000 | >10,000 | >10,000 | 1,231 | 2,531 |
| 5-MeO-MiPT | 12 | 303 | 23 | 3,496 | 448 | 59 | 2,186 | >10,000 | 953 | 130 | 20 | 6,409 |
| 6-Fluoro-DMT | 393 | 218 | 55 | 461 | 866 | 30 | 674 | >10,000 | 961 | 26 | 41 | 145 |
| 5-MeO-TMT | 200 | >10,000 | 250 | 1,800 | >10,000 | ? | 4,020 | ? | 10,450 | 60 | 145 | >10,000 |
| EMDT | 170 | >10,000 | 290 | 520 | >10,000 | ? | 1,810 | ? | 4,620 | 16 | 300 | >10,000 |
| Ibogaine | >10,000 | >10,000 | >10,000 | ? | 14,142 | ? | >10,000 | >10,000 | ? | ? | ? | 549 |
| LSD | 7.3 | 3.9 | 7.8 | 93 | 11 | 30 | 31 | >10,000 | 9 | 6.9 | 6.6 | >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.[36][37][38] Other tryptamine synthesis routes have also been described, for instance starting with tryptamine rather than indole.[36][37]
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List of substituted tryptamines
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Perspective
 |
More information Structure, Name ...
| Structure | Name | Origin | Ring sub. | RN1 | RN2 | Chemical name | CAS # |
|---|---|---|---|---|---|---|---|
| Tryptamine (T) | Animals, plants, fungi | H | H | H | 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine | 61-54-1 |
 | NMT | Plants | H | H | CH3 | N-methyltryptamine | 61-49-4 |
 | 2-HO-NMT | Plants | 2-OH | H | CH3 | 2-hydroxy-N-methyltryptamine | 106987-89-7 |
 | 5-MeO-NMT | Plants | 5-OCH3 | H | CH3 | 5-methoxy-N-methyltryptamine | 2009-03-2 |
 | Serotonin (5-HT) | Animals, plants | 5-OH | H | H | 5-hydroxytryptamine | 50-67-9 |
 | N-Methylserotonin (NMS; norbufotenin; 5-HO-NMT) | Plants | 5-OH | H | CH3 | 5-hydroxy-N-methyltryptamine | 1134-01-6 |
 | Bufotenin (5-HO-DMT) | Animals, plants, fungi | 5-OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyltryptamine | 487-93-4 |
 | Bufotenidine (5-HTQ) | Amphibians | 5-O− | (CH3)3 | 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate | 487-91-2 | |
 | Bufoviridine (5-SO-DMT) | Amphibians | 5-SO | CH3 | CH3 | 5-sulfooxy-N,N-dimethyltryptamine | 16369-08-7 |
 | Melatonin (5-MeO-NAcT) | Animals, plants, microbes | 5-OCH3 | H | O=C-CH3 | 5-methoxy-N-acetyltryptamine | 73-31-4 |
 | N-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT) | Animals | 5-OH | H | O=C-CH3 | 5-hydroxy-N-acetyltryptamine | 1210-83-9 |
 | 6-Hydroxymelatonin | Animals | 5-OCH3, 6-OH | H | O=C-CH3 | N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide | 2208-41-5 |
 | 4-Hydroxytryptamine (4-HT) | Fungi | 4-OH | H | H | 4-hydroxytryptamine | 570-14-9 |
 | 4-HO-NMT | Fungi | 4-OH | H | CH3 | 4-hydroxy-N-methyltryptamine | 28363-70-4 |
 | Psilocin (4-HO-DMT) | Fungi | 4-OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyltryptamine | 520-53-6 |
 | 4-HO-TMT | Fungi | 4-OH | CH3 | CH3 | 4-hydroxy-N,N,N-trimethyltryptammonium | 262285-41-6 |
 | Norbaeocystin (4-PO-T) | Fungi | 4-OPO3H2 | H | H | 4-phosphoryloxy-tryptamine | 21420-59-7 |
 | Baeocystin (4-PO-NMT) | Fungi | 4-OPO3H2 | H | CH3 | 4-phosphoryloxy-N-methyl-tryptamine | 21420-58-6 |
 | Psilocybin (4-PO-DMT) | Fungi | 4-OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyltryptamine | 520-52-5 |
 | Aeruginascin (4-PO-TMT) | Fungi | 4-OPO3H2 | (CH3)3 | [3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate | 114264-95-8 | |
 | DMT | Animals, plants | H | CH3 | CH3 | N,N-dimethyltryptamine | 61-50-7 |
 | Lespedamine (1-MeO-DMT) | Plants | 1-OCH3 | CH3 | CH3 | 1-methoxy-N,N-dimethyltryptamine | 4335-93-7 |
 | 5-MeO-DMT (mebufotenin) | Animals, plants | 5-OCH3 | CH3 | CH3 | 5-methoxy-N,N-dimethyltryptamine | 1019-45-0 |
 | 5-Bromo-DMT | Marine sponges, invertebrates | 5-Br | CH3 | CH3 | 5-bromo-N,N-dimethyltryptamine | 17274-65-6 |
 | 6-Bromotryptamine | Marine invertebrates | 6-Br | H | H | 6-bromotryptamine | 96624-18-9 |
 | 5,6-Dibromotryptamine | Marine invertebrates | 5,6-Br | H | H | 5,6-dibromotryptamine | |
 | 5,6-Dibromo-NMT | Marine invertebrates | 5,6-Br | H | CH3 | 5,6-dibromo-N-methyltryptamine | |
 | 5,6-Dibromo-DMT | Marine sponges, invertebrates | 5,6-Br | CH3 | CH3 | 5,6-dibromo-N,N-dimethyltryptamine | 72853-80-6 |
 | Desformylflustrabromine (dFBr) | Marine invertebrates | 2-(α,α-dimethylallyl), 6-Br | H | CH3 | 2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine | 474657-72-2 |
 | Convolutindole A | Marine invertebrates | 2,4,6-Br, 1,7-OCH3 | CH3 | CH3 | 1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine | 443356-86-3 |
 | Acetryptine (5-AT) | artificial | 5-COCH3 | H | H | 5-Acetyltryptamine | 3551-18-6 |
 | 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-NOT | artificial | 5-O(CH2)8CH3 | H | H | 5-Nonyloxytryptamine | 157798-12-4 |
 | 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 |
 | 4-HO-NBnT | artificial | 4-OH | H | CH2C6H5 | 4-hydroxy-N-benzyltryptamine | |
 | 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-MT-NB3OMe [39] | artificial | 5-OCH3 | H | CH2C6H4(m-OCH3) | 5-methoxy-N-(meta-methoxybenzyl)tryptamine | 1648553-42-7 |
tryptamine).svg) | 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 [40] | 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[41] | 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 [42] | artificial | 4-OH | cis-(CHCH3)CH2(CHCH3) | 3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol | ||
 | Pyr-T | artificial | H | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole | 14008-96-9 | |
 | 4-HO-pyr-T | artificial | 4-OH | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol | 63097-26-7 | |
 | Cis-2',5'-dimethyl-4-HO-pyr-T [42] | artificial | 4-OH | cis-(CHCH3)CH2CH2(CHCH3) | 3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol | ||
 | 5-MeO-pyr-T | artificial | 5-OCH3 | (CH2)4 | 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole | 3949-14-2 | |
 | 4-F-5-MeO-pyr-T | artificial | 4-F-5-OCH3 | (CH2)4 | 4-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole | 344790-93-8 | |
 | Pip-T | artificial | H | (CH2)5 | 3-(2-Piperidin-1-ylethyl)-1H-indole | 26628-87-5 | |
 | 5-MeO-pip-T | artificial | 5-OCH3 | (CH2)5 | 5-Methoxy-3-(2-piperidin-1-ylethyl)-1H-indole | ||
 | 5-MeO-IsoqT | artificial | 5-OCH3 | ? | 3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-5-methoxy-1H-indole | ||
 | Indolylethylfentanyl | artificial | H | (CH2)5-4-N(COCH2CH3)C6H5 | N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide | 58399-46-5 | |
 | 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 | |
 | 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 |
 | iPALT (ALiPT) | artificial | H | H2C=CH-CH2 | CH(CH3)2 | N-allyl-N-isopropyltryptamine | |
 | 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 |
 | 4-Amino-DMT [43] | 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 | |
 | 4-AcO-DMT | 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 | 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-PO-MET | artificial | 4-OPO3H2 | CH3 | CH2CH3 | 4-phosphoryloxy-N-methyl-N-ethyltryptamine | |
 | 4-HO-DET | 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 | 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-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-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[44] | artificial | 4-OH | CH3 | H2C=CH-CH2 | 4-hydroxy-N-Methyl-N-allyltryptamine | |
 | 4-AcO-MALT[45] | artificial | 4-OCOCH3 | CH3 | H2C=CH-CH2 | 4-acetoxy-N-Methyl-N-allyltryptamine | |
 | 4-HO-NALT[46] | artificial | 4-OH | H | H2C=CH-CH2 | 4-hydroxy-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[47] | 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-HO-McPeT | artificial | 4-OH | C5H9 | CH3 | 4-hydroxy-N-cyclopentyl-N-methyltryptamine | 77872-48-1 |
 | 4-HO-McPMT [48] | 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 |
 | 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-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 | artificial | 5-OCOCH3 | CH3 | CH3 | 5-acetoxy-N,N-dimethyltryptamine | 16977-50-7 |
 | 5-AcO-MET [49] | 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 [50] | 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-DMT | artificial | 5-OCH2CH3 | CH3 | CH3 | 5-ethoxy-N,N-dimethyltryptamine | 855245-09-9 |
 | 5-Ethoxy-MET | artificial | 5-OCH2CH3 | CH3 | CH2CH3 | 5-ethoxy-N-methyl-N-ethyltryptamine | |
 | 5-Ethoxy-DET | artificial | 5-OCH2CH3 | CH2CH3 | CH2CH3 | 5-ethoxy-N,N-diethyltryptamine | |
 | 5-Ethoxy-MPT | artificial | 5-OCH2CH3 | CH3 | CH2CH2CH3 | 5-ethoxy-N-methyl-N-propyltryptamine | |
 | 5-Ethoxy-EPT | artificial | 5-OCH2CH3 | CH2CH3 | CH2CH2CH3 | 5-ethoxy-N-ethyl-N-propyltryptamine | |
 | 5-Ethoxy-DPT | artificial | 5-OCH2CH3 | CH2CH2CH3 | CH2CH3 | 5-ethoxy-N,N-dipropyltryptamine | |
 | 5-Ethoxy-MiPT | artificial | 5-OCH2CH3 | CH3 | CH(CH3)2 | 5-ethoxy-N-methyl-N-isopropyltryptamine | |
 | 5-Ethoxy-EiPT | artificial | 5-OCH2CH3 | CH2CH3 | CH(CH3)2 | 5-ethoxy-N-ethyl-N-isopropyltryptamine | |
 | 5-Ethoxy-DiPT | artificial | 5-OCH2CH3 | CH(CH3)2 | CH(CH3)2 | 5-ethoxy-N,N-diisopropyltryptamine | |
 | 5-Ethoxy-DALT | artificial | 5-OCH2CH3 | H2C=CH-CH2 | H2C=CH-CH2 | 5-ethoxy-N,N-diallyltryptamine | |
 | 5-BnO-DMT | artificial | 5-OCH2C6H5 | CH3 | CH3 | 5-benzyloxy-N,N-dimethyltryptamine | 101832-88-6 |
 | 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) | artificial | 5-CH3 | CH3 | CH3 | 5,N,N-trimethyltryptamine | 22120-39-4 |
 | 5-Ethyl-DMT | artificial | 5-CH2CH3 | CH3 | CH3 | 5-ethyl-N,N-dimethyltryptamine | 171783-25-8 |
 | 5-Isopropyl-DMT | artificial | 5-CH(CH3)2 | CH3 | CH3 | 5-isopropyl-N,N-dimethyltryptamine | 156281-04-8 |
 | 5-(t-Butyl)-DMT [51] | artificial | 5-C(CH3)3 | CH3 | CH3 | 5-(tert-butyl)-N,N-dimethyltryptamine | |
 | 5-Fluoro-DMT | artificial | 5-F | CH3 | CH3 | 5-fluoro-N,N-dimethyltryptamine | 22120-36-1 |
 | Bretisilocin (5-fluoro-MET; GM-2505) | artificial | 5-F | CH3 | CH2CH3 | 5-fluoro-N-methyl-N-ethyltryptamine | 2698331-35-8 |
 | 5-Fluoro-DET | artificial | 5-F | CH2CH3 | CH2CH3 | 5-fluoro-N,N-diethyltryptamine | |
 | 5-Fluoro-EPT | artificial | 5-F | CH2CH3 | CH2CH2CH3 | 5-fluoro-N-ethyl-N-propyltryptamine | |
 | 5-Fluoro-DPT | artificial | 5-F | CH2CH2CH3 | CH2CH2CH3 | 5-fluoro-N,N-dipropyltryptamine | |
 | 5-Fluoro-PiPT | artificial | 5-F | CH2CH2CH3 | CH(CH3)2 | 5-fluoro-N-propyl-N-isopropyltryptamine | |
 | 5-Fluoro-PcBT | artificial | 5-F | CH2CH2CH3 | CH(CH2)3 | 5-fluoro-N-propyl-N-cyclobutyltryptamine | |
 | 5-Fluoro-iPcBT | artificial | 5-F | CH(CH3)2 | CH(CH2)3 | 5-fluoro-N-isopropyl-N-cyclobutyltryptamine | |
 | 5-Fluoro-DiPT | artificial | 5-F | CH(CH3)2 | CH(CH3)2 | 5-fluoro-N,N-diisoproptryptamine | |
 | 5-Fluoro-sBALT | artificial | 5-F | CH(CH3)CH2CH3 | CH2CH=CH2 | 5-fluoro-N-sec-butyl-N-allyltryptamine | |
 | 5-Fluoro-M1MALT | artificial | 5-F | CH3 | CH(CH3)CH=CH2 | 5-fluoro-N-methyl-N-(1-methylallyl)tryptamine | |
 | 5-Chloro-DMT | artificial | 5-Cl | CH3 | CH3 | 5-chloro-N,N-dimethyltryptamine | 22120-32-7 |
 | 5-Iodo-DMT | artificial | 5-I | CH3 | CH3 | 5-iodo-N,N-dimethyltryptamine | 22120-38-3 |
 | 5-TFM-DMT | artificial | 5-CF3 | CH3 | CH3 | 5-(trifluoromethyl)-N,N-dimethyltryptamine | 2418713-32-1 |
 | 5-TFMO-DMT[52] | artificial | 5-OCF3 | CH3 | CH3 | 5-(trifluoromethoxy)-N,N-dimethyltryptamine | |
 | 5-Nitro-DMT[53] | artificial | 5-NO2 | CH3 | CH3 | 5-nitro-N,N-dimethyltryptamine | 69937-13-9 |
 | 5-CN-DMT | artificial | 5-C≡N | CH3 | CH3 | 5-cyano-N,N-dimethyltryptamine | 17380-42-6 |
 | 5-CN-DPT | artificial | 5-C≡N | CH2CH2CH3 | CH2CH2CH3 | 5-cyano-N,N-dipropyltryptamine | 74885-19-1 |
 | 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-DMT | artificial | 6-F | CH3 | CH3 | 6-fluoro-N,N-dimethyltryptamine | 1511-31-5 |
 | 6-Fluoro-DET[54] | artificial | 6-F | CH2CH3 | CH2CH3 | 6-fluoro-N,N-diethyltryptamine | 2836-69-3 |
 | 6-Chloro-DMT | artificial | 6-Cl | CH3 | CH3 | 6-chloro-N,N-dimethyltryptamine | 25390-72-1 |
 | 6-Methyl-DMT | artificial | 6-CH3 | CH3 | CH3 | 6,N,N-trimethyltryptamine | |
 | 6-Hydroxy-DMT | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-dimethyltryptamine | 1476-33-1 |
 | 6-Hydroxy-DET | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-diethyltryptamine | 1476-59-1 |
 | 6-Methoxy-DMT | artificial | 6-OCH3 | CH3 | CH3 | 6-methoxy-N,N-dimethyltryptamine | 2426-88-2 |
 | 7-Methyl-DMT | artificial | 7-CH3 | CH3 | CH3 | 7,N,N-trimethyltryptamine | 65882-39-5 |
 | 7-Ethyl-DMT | artificial | 7-CH2CH3 | CH3 | CH3 | 7-ethyl-N,N-dimethyltryptamine | |
 | 7-Chloro-DMT | artificial | 7-Cl | CH3 | CH3 | 7-chloro-N,N-dimethyltryptamine | |
 | 7-Bromo-DMT[55] | artificial | 7-Br | CH3 | CH3 | 7-bromo-N,N-dimethyltryptamine | 74798-68-8 |
 | 7-Methoxy-DMT | artificial | 7-OCH3 | CH3 | CH3 | 7-methoxy-N,N-dimethyltryptamine | |
 | 7-Methoxy-MiPT | artificial | 7-OCH3 | CH3 | CH(CH3)2 | 7-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-Fluoropsilocin | artificial | 4-OH,6-F | CH3 | CH3 | 4-hydroxy-6-fluoro-N,N-dimethyltryptamine | 312314-12-8 |
 | 6-Fluoro-5-MeO-DMT | artificial | 5-OCH3,6-F | CH3 | CH3 | 5-methoxy-6-fluoro-N,N-dimethyltryptamine | |
 | 5,6-Difluoro-EPT | artificial | 5-F, 6-F | CH2CH3 | CH2CH2CH3 | 5,6-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 |
 | 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[56] | 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 | |
| Structure | Short Name | Origin | Ring Substitution | RN1 | RN2 | Full Name | CAS # |
Close
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.[57][58][59] 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.[59] This is analogous to α-methylation of phenethylamine into amphetamine.[59]
Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[60][61][62][63] and produce psychostimulant, entactogen, and/or psychedelic effects.[57][58][59] The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[58][59] In accordance with its action as a dual releasing agent of serotonin and dopamine, αET 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 αMT, 5-MeO-αMT, and various others.[64]
More information Structure, Name ...
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
 |
Tryptophan | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid | 73-22-3 |
.svg) |
5-Hydroxytryptophan (5-HTP) | 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid | 4350-09-8 |
 |
αMT (AMT; Indopan) | 1-(1H-Indol-3-yl)propan-2-amine | 299-26-3 |
 |
4-HO-αMT | 3-(2-aminopropyl)-1H-indol-4-ol | 15066-09-8 |
 |
4-Methyl-αMT | 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine | 3569-29-7 |
 |
5-Fluoro-αMT | 1-(5-fluoro-1H-indol-3-yl)propan-2-amine | 712-08-3 |
indole.svg) |
5-Chloro-αMT | 1-(5-Chloro-1H-indol-3-yl)propan-2-amine | 712-07-2 |
 |
5-HO-αMT (αMS/α-methyl-5-HT) | 3-(2-aminopropyl)-1H-indol-5-ol | 304-52-9 |
 |
5-MeO-αMT | 1-(5-methoxy-1H-indol-3-yl)propan-2-amine | 1137-04-8 |
 |
5-Ethoxy-αMT | 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine | 101832-83-1 |
 |
5-Isopropoxy-αMT | 1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine | |
 |
5-Allyloxy-αMT | 1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine | |
 |
BW-723C86 | 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine | 160521-72-2 |
 |
6-Fluoro-αMT | 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-αMT) | (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole | 362603-40-5 |
 |
Compound 5 [65] | 1-(3H-benzo[e]indol-1-yl)propan-2-amine | |
 |
αET | 1-(1H-indol-3-yl)butan-2-amine | 2235-90-7 |
 |
4-Methyl-αET | 1-(4-Methyl-1H-indol-3-yl)butan-2-amine | 28289-30-7 |
 |
4-HO-αET | 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine | 28289-28-3 |
 |
5-Fluoro-αET | 1-(5-fluoro-1H-indol-3-yl)butan-2-amine | 1380137-98-3 |
 |
5-Methyl-αET | 1-(5-methyl-1H-indol-3-yl)butan-2-amine | 1380148-21-9 |
 |
5-MeO-αET | 1-(5-methoxy-1H-indol-3-yl)butan-2-amine | 4765-10-0 |
 |
7-Methyl-αET | 1-(7-methyl-1H-indol-3-yl)butan-2-amine | 13712-80-6 |
 |
N-Methyl-5-MeO-αMT (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 |
 |
Indolylpropylaminopentane (IPAP; α,N-DPT) | 1-(1H-indol-3-yl)-N-propylpentan-2-amine | |
 |
N,N-Dimethyl-αMT (α,N,N-TMT) | (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine | 4761-32-4 |
 |
N,N-Dimethyl-5-MeO-αMT (5-MeO-α,N,N-TMT) | (2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine | 101831-90-7 |
 |
α-Methyl-DiPT | (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine | |
 |
MPMI[66] | 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole | 143321-54-4 |
 |
Lucigenol (4-HO-MPMI) | (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole | 250672-65-2 |
 |
5-MeO-MPMI (CP-108509) | 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole | 143321-57-7 |
 |
5F-MPMI[67] | (R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole | |
 |
5-Br-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[41][68] | 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine | |
 |
BK-NM-AMT (α,N-dimethyl-β-ketotryptamine)[69][70][71] | 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one | |
 |
BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine)[72][73][74][71] | 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one | |
 |
BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[74][75][76] | 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one | |
 |
BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine)[74][77][78] | 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one |
Close
List of substituted β-ketotryptamines
A number of β-ketotryptamines (beta-ketotryptamines) are known.[69][71][74] 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.[69][71][74] They act as monoamine releasing agents.[69][71][74]
Cyclized tryptamines
Examples of cyclized tryptamines include:
- β-Carbolines such as harmala alkaloids like harmaline
- Ibogalogs (hexahydroazepinoindoles) such as ibogainalog, tabernanthalog, PNU-22394, and PHA-57378
- Iboga alkaloids like ibogaine, noribogaine, ibogamine, and tabernanthine
- Ergolines and lysergamides such as lysergic acid diethylamide (LSD) and ergot alkaloids like ergine (lysergic acid amide; LSA)
- Partial ergolines and lysergamides like RU-27849, FHATHBIN, NDTDI, and CT-5252
- Mitragyna alkaloids such as mitragynine
- Yohimbans such as Rauvolfia and Corynanthe alkaloids like yohimbine and rauwolscine
- Pertines (phenylpiperazinylethylindoles) like alpertine, milipertine, oxypertine, and solypertine
- Imidazolylindoles like AGH-107, AGH-192, and AH-494
- Morpholinylethylindoles like mor-T and 5-MeO-mor-T
- Piperidinylethylindoles like pip-T and 5-MeO-pip-T
- Pyrrolidinylethylindoles like pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, and 4-F-5-MeO-pyr-T
- Pyrrolidinylmethylindoles like MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-135807, and eletriptan
- Tetrahydropyridinylindoles like RS134-49 (4-Me-THPI), RU-28253 (5-MeO-THPI), and NEtPhOH-THPI
- Tetrahydrocarbazolamines like ciclindole, flucindole, frovatriptan, LY-344864, and ramatroban
- Tetrahydropyrroloquinolines like bufothionine and O-methylnordehydrobufotenine
- Others like 5-MeO-IsoqT, barettin, cyclic 3-hydroxymelatonin, and metralindole
Other closely related cyclized tryptamine-like compounds include the following:
- Piperidinylindoles like SN-22, BRL-54443, naratriptan, LY-334370, and sertindole
- Tetrahydropyridinylindoles like RU-24969, EMD-386088, and LY-367,265
- Tetrahydropyridinylindazoles like VU6067416
- Tetrahydropyridinylpyrrolopyridines like (R)-69, (R)-70, and CP-94253
- Pyridopyrroloquinoxalines (tetracyclic γ-carbolines) like lumateperone, IHCH-7113, IHCH-7086, and ITI-1549
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Related compounds
Summarize
Perspective
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[79] | 2-(3H-inden-1-yl)-N,N-dimethylethanamine | |
 |
Dimemebfe (5-MeO-BFE) | 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine | 140853-58-3 |
 |
5-MeO-DiBF | N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine | |
 |
3-APB | 3-(2-aminopropyl)benzofuran | 105909-13-5 |
 |
3-APBT (SKF-6678) | 1-(1-benzothiophen-3-yl)propan-2-amine | 1201-27-0 |
 |
Mebfap (5-MeO-3-APB) | 3-(2-aminopropyl)-5-methoxybenzofuran | 140853-59-4 |
 |
Isotryptamine (isoT) | 2-indol-1-ylethanamine | 13708-58-2 |
 |
isoAMT | 1-indol-1-ylpropan-2-amine | 1227465-67-9 |
-5,6-Difluoro-isoAMT.svg) |
(S)-5,6-Difluoro-isoAMT [80] | (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 | |
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1ZP2MA | 1-indolizin-1-yl-N-methylpropan-2-amine | |
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1Z2MAP1O | 1-indolizin-3-yl-2-(methylamino)propan-1-one | 2110204-31-2 |
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Example 16 [81][82] | 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine | |
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Example 1 [83] | 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine | |
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VER-3323 | (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine | 259857-99-3 |
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AL-34662 (indazole-5-HO-AMT) | 1-((S)-2-Aminopropyl)-1H-indazol-6-ol | 210580-75-9 |
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O-Methyl-AL-34662 (indazole-5-MeO-AMT) | 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole | 210580-60-2 |
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7-Methyl-AL-34662 | 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol | 874668-67-4 |
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7-Chloro-AL-34662 | 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol | 874881-86-4 |
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AL-38022A | (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine | 478132-11-5 |
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Example 9 [84] | (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine | 478132-12-6 |
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Example 3 [85] | (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine | 890087-75-9 |
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Example 1 [86] | (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine | 1373917-69-1 |
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YM-348 | (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine | 372163-84-3 |
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2-Desethyl-YM-348 [87] | (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine | 748116-94-1 |
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I-32 [88] | 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol | |
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2-Azapsilocin (Psilocin indazole analogue, P-6)[89] | 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol | |
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4-Aza-5-MeO-DPT (P-11) | N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine | |
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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 | |
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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 | |
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RS134-49 (4-Me-THPI) | 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | 2945139-94-4 |
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RU-28253 (5-MeO-THPI) | 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | |
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NEtPhOH-THPI (compound 24c) | 3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | |
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VU6067416[90] | 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole | 3027515-24-5 |
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(R)-69 | 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine | 2765652-48-8 |
-1H-indole.svg) |
SN-22 | 3-(1-methylpiperidin-4-yl)-1H-indole | 17403-07-5 |
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RU-24,969 | 5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole | 107008-28-6 |
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EMD-386088 | 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole | 54635-62-0 |
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Overview table
More information Simple, 4-Hydroxy ...
| Simple | 4-Hydroxy | 4-Acetoxy | 5-Methoxy | 5-Hydroxy | |
|---|---|---|---|---|---|
| Tryptamine (T) | 4-HO-T (dinorpsilocin) | 4-AcO-T | 5-MeO-T (O-methylserotonin) | 5-HO-T (serotonin; 5-HT) | |
| NAcT | 4-HO-NAcT | 4-AcO-NAcT | 5-MeO-NAcT (melatonin) | 5-HO-NAcT (normelatonin; NAS) | |
| NMT | 4-HO-NMT (norpsilocin) | 4-AcO-NMT | 5-MeO-NMT | 5-HO-NMT (N-methylserotonin) | |
| NET | 4-HO-NET | 4-AcO-NET | 5-MeO-NET | 5-HO-NET | |
| NPT | 4-HO-NPT | 4-AcO-NPT | 5-MeO-NPT | 5-HO-NPT | |
| NiPT | 4-HO-NiPT | 4-AcO-NiPT | 5-MeO-NiPT | 5-HO-NiPT | |
| NALT | 4-HO-NALT | 4-AcO-NALT | 5-MeO-NALT | 5-HO-NALT | |
| NBT | 4-HO-NBT | 4-AcO-NBT | 5-MeO-NBT | 5-HO-NBT | |
| NiBT | 4-HO-NiBT | 4-AcO-NiBT | 5-MeO-NiBT | 5-HO-NiBT | |
| NsBT | 4-HO-NsBT | 4-AcO-NsBT | 5-MeO-NsBT | 5-HO-NsBT | |
| NtBT | 4-HO-NtBT | 4-AcO-NtBT | 5-MeO-NtBT | 5-HO-NtBT | |
| NAT | 4-HO-NAT | 4-AcO-NAT | 5-MeO-NAT | 5-HO-NAT | |
| NHT | 4-HO-NHT | 4-AcO-NHT | 5-MeO-NHT | 5-HO-NHT | |
| NcPT | 4-HO-NcPT | 4-AcO-NcPT | 5-MeO-NcPT | 5-HO-NcPT | |
| NBnT | 4-HO-NBnT | 4-AcO-NBnT | 5-MeO-NBnT | 5-HO-NBnT | |
| NBOMeT | 4-HO-NBOMeT | 4-AcO-NBOMeT | 5-MeO-NBOMeT | 5-HO-NBOMeT | |
| NB3OMeT | 4-HO-NB3OMeT | 4-AcO-NB3OMeT | 5-MeO-NB3OMeT | 5-HO-NB3OMeT | |
| DMT | 4-HO-DMT (psilocin) | 4-AcO-DMT (psilacetin) | 5-MeO-DMT (mebufotenin) | 5-HO-DMT (bufotenin) | |
| DET | 4-HO-DET (ethocin) | 4-AcO-DET (ethacetin) | 5-MeO-DET | 5-HO-DET | |
| DPT | 4-HO-DPT (deprocin) | 4-AcO-DPT (depracetin) | 5-MeO-DPT | 5-HO-DPT (DiPS, NDPS) | |
| DiPT | 4-HO-DiPT (iprocin) | 4-AcO-DiPT (ipracetin) | 5-MeO-DiPT (foxy) | 5-HO-DiPT | |
| DALT | 4-HO-DALT (daltocin) | 4-AcO-DALT (dalcetin) | 5-MeO-DALT (foxtrot) | 5-HO-DALT | |
| DBT | 4-HO-DBT | 4-AcO-DBT | 5-MeO-DBT | 5-HO-DBT | |
| DiBT | 4-HO-DiBT | 4-AcO-DiBT | 5-MeO-DiBT | 5-HO-DiBT | |
| DsBT | 4-HO-DsBT | 4-AcO-DsBT | 5-MeO-DsBT | 5-HO-DsBT | |
| DtBT | 4-HO-DtBT | 4-AcO-DtBT | 5-MeO-DtBT | 5-HO-DtBT | |
| DAT | 4-HO-DAT | 4-AcO-DAT | 5-MeO-DAT | 5-HO-DAT | |
| DHT | 4-HO-DHT | 4-AcO-DHT | 5-MeO-DHT | 5-HO-DHT | |
| DcPT | 4-HO-DcPT | 4-AcO-DcPT | 5-MeO-DcPT | 5-HO-DcPT | |
| MET | 4-HO-MET (metocin) | 4-AcO-MET (metacetin) | 5-MeO-MET | 5-HO-MET | |
| MPT | 4-HO-MPT (meprocin) | 4-AcO-MPT | 5-MeO-MPT | 5-HO-MPT | |
| MiPT | 4-HO-MiPT (miprocin) | 4-AcO-MiPT (mipracetin) | 5-MeO-MiPT (moxy) | 5-HO-MiPT | |
| MALT | 4-HO-MALT (maltocin) | 4-AcO-MALT | 5-MeO-MALT | 5-HO-MALT | |
| MBT | 4-HO-MBT | 4-AcO-MBT | 5-MeO-MBT | 5-HO-MBT | |
| MiBT | 4-HO-MiBT | 4-AcO-MiBT | 5-MeO-MiBT | 5-HO-MiBT | |
| MsBT | 4-HO-MsBT | 4-AcO-MsBT | 5-MeO-MsBT | 5-HO-MsBT | |
| MtBT | 4-HO-MtBT | 4-AcO-MtBT | 5-MeO-MtBT | 5-HO-MtBT | |
| McPT | 4-HO-McPT | 4-AcO-McPT | 5-MeO-McPT | 5-HO-McPT | |
| McPMT | 4-HO-McPMT | 4-AcO-McPMT | 5-MeO-McPMT | 5-HO-McPMT | |
| McPeT | 4-HO-McPeT | 4-AcO-McPeT | 5-MeO-McPeT | 5-HO-McPeT | |
| EPT | 4-HO-EPT (eprocin) | 4-AcO-EPT | 5-MeO-EPT | 5-HO-EPT | |
| EiPT | 4-HO-EiPT (eiprocin) | 4-AcO-EiPT | 5-MeO-EiPT | 5-HO-EiPT | |
| EALT | 4-HO-EALT | 4-AcO-EALT | 5-MeO-EALT | 5-HO-EALT | |
| EBT | 4-HO-EBT | 4-AcO-EBT | 5-MeO-EBT | 5-HO-EBT | |
| EiBT | 4-HO-EiBT (eibucin) | 4-AcO-EiBT | 5-MeO-EiBT | 5-HO-EiBT | |
| EsBT | 4-HO-EsBT | 4-AcO-EsBT | 5-MeO-EsBT | 5-HO-EsBT | |
| EtBT | 4-HO-EtBT | 4-AcO-EtBT | 5-MeO-EtBT | 5-HO-EtBT | |
| EcPT | 4-HO-EcPT | 4-AcO-EcPT | 5-MeO-EcPT | 5-HO-EcPT | |
| PiPT | 4-HO-PiPT (piprocin) | 4-AcO-PiPT | 5-MeO-PiPT | 5-HO-PiPT | |
| PALT | 4-HO-PALT | 4-AcO-PALT | 5-MeO-PALT | 5-HO-PALT | |
| PBT | 4-HO-PBT | 4-AcO-PBT | 5-MeO-PBT | 5-HO-PBT | |
| PiBT | 4-HO-PiBT | 4-AcO-PiBT | 5-MeO-PiBT | 5-HO-PiBT | |
| PsBT | 4-HO-PsBT | 4-AcO-PsBT | 5-MeO-PsBT | 5-HO-PsBT | |
| PtBT | 4-HO-PtBT | 4-AcO-PtBT | 5-MeO-PtBT | 5-HO-PtBT | |
| PcPT | 4-HO-PcPT | 4-AcO-PcPT | 5-MeO-PcPT | 5-HO-PcPT | |
| iPALT (ALiPT) | 4-HO-iPALT | 4-AcO-iPALT | 5-MeO-iPALT (ASR-3001) | 5-HO-iPALT | |
| iPBT (BiPT) | 4-HO-iPBT | 4-AcO-iPBT | 5-MeO-iPBT | 5-HO-iPBT | |
| iPiBT | 4-HO-iPiBT | 4-AcO-iPiBT | 5-MeO-iPiBT | 5-HO-iPiBT | |
| iPsBT | 4-HO-iPsBT | 4-AcO-iPsBT | 5-MeO-iPsBT | 5-HO-iPsBT | |
| iPtBT | 4-HO-iPtBT | 4-AcO-iPtBT | 5-MeO-iPtBT | 5-HO-iPtBT | |
| iPcPT | 4-HO-iPcPT | 4-AcO-iPcPT | 5-MeO-iPcPT | 5-HO-iPcPT | |
| TMT | 4-HO-TMT | 4-AcO-TMT | 5-MeO-TMT | 5-HO-TMT | |
| Pyr-T | 4-HO-pyr-T | 4-AcO-pyr-T | 5-MeO-pyr-T | 5-HO-pyr-T | |
| Pip-T | 4-HO-pip-T | 4-AcO-pip-T | 5-MeO-pip-T | 5-HO-pip-T | |
| Mor-T | 4-HO-mor-T | 4-AcO-mor-T | 5-MeO-mor-T | 5-HO-mor-T | |
| MPMI | 4-HO-MPMI (lucigenol) | 4-AcO-MPMI | 5-MeO-MPMI (CP-108509) | 5-HO-MPMI | |
| THPI | 4-HO-THPI | 4-AcO-THPI | 5-MeO-THPI (RU-28253) | 5-HO-THPI | |
| IsoqT | 4-HO-IsoqT | 4-AcO-IsoqT | 5-MeO-IsoqT | 5-HO-IsoqT | |
| 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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See also
- Substituted β-carboline
- Ibogalog
- Iboga alkaloid
- Lysergamide
- TiHKAL
- List of miscellaneous 5-HT2A receptor agonists
- Substituted isotryptamine
- Indazolylethylamine
- Indolizinylethylamine
- Tetrahydropyridinylpyrrolopyridine
- Substituted 2-aminoindane
- Substituted amphetamine
- Substituted benzofuran
- Substituted cathinone
- Substituted methylenedioxyphenethylamine
- Substituted phenethylamine
- 2C, DOx, 25-NB
References
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