

Substituted tryptamines, or simplytryptamines, also known asserotonin analogues (i.e.,5-hydroxytryptamine analogues), areorganic compounds which may be thought of as being derived fromtryptamine itself. The molecular structures of all tryptamines contain anindole ring system, joined to anamino (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 includeserotonin, an importantneurotransmitter, andmelatonin, ahormone involved in regulating the sleep-wake cycle. Tryptaminealkaloids are found infungi,plants andanimals; and sometimes used byhumans for the neurological orpsychotropic effects of the substance. Prominent examples of tryptamine alkaloids includepsilocybin (from "psilocybin mushrooms") andDMT. In South America, dimethyltryptamine is obtained from numerous plant sources, likechacruna, and it is often used inayahuasca brews. Manysynthetic tryptamines have also been made, including themigrainedrugsumatriptan, andpsychedelic 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 examplecyclized tryptamines likeLSD,ibogaine,harmaline,mitragynine andyohimbine. A thorough investigation of dozens of tryptamine compounds was published byAlexander Shulgin andAnn Shulgin in 1997 under the titleTiHKAL (Tryptamines I Have Known and Loved).[2]
Thedoses,potencies,durations, and effects of psychedelic tryptamines have been reviewed byAlexander Shulgin and other authors.[3][4][5][6][2][7][8][9][10][11]
| 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 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+) | 6–8 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 | |
| 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 | |
| Footnotes:a =Tryptamine is notorally active, but is activeintravenously at a dose of 250 mg with a very shortduration.b =NMT is not orally active, but is said to be activesmoked at a dose of 50 to 120 mg with a duration of seconds to minutes. Also reportedly orally active with anMAOITooltip monoamine oxidase inhibitor.c =DMT is activeparenterally at doses of 50 to 100 mg (2–100 mg) smoked,intramuscularly, orsubcutaneously and at doses of 4 to 30 mgintravenously (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 anMAOI (as inayahuasca orpharmahuasca), with a typical dose of 50 mg (range 20–120 mg) and a duration of 4 to 6 hours.Refs:[3][4][2][7][8][9][11]Individual:[12][13][14][15][16][17][18][19][20][21][22] | ||||
| 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 activesubcutaneously at doses of 5 to 40 mg with an averageduration of 3.6 hours.Refs:[3][4][2][7][8][9][11]Individual:[14][15][23][24] | ||||
| 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 theblood–brain barrier and is notpsychoactive.b =Bufotenin is notorally active, but is active atintravenously at doses of 8 to 16 mg with aduration of 1 to 2 hours and is active viainsufflation and otherparenteralroutes.Refs:[3][4][2][11]Individual:[25][26][27][28] | ||||
| 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 | |
| ASR-3001 (5-MeO-iPALT) | 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 notorally active, but is active at a dose of 2 to 20 mgsmoked or 2 to 3 mgintravenously, with aduration of 5 to 20 minutes. Also orally active with anMAOITooltip monoamine oxidase inhibitor at doses of 10 to 25 mg.b =Melatonin is not a psychedelic but ahypnotic and is non-hallucinogenic at doses of up to 1,200 mg.Refs:[3][4][2][7][8][9][11]Individual:[15][18] | ||||
| 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 | 4-Hydroxy-α-methyltryptamine | 15–20 mg+ | Unknown | |
| 4-Methyl-AMT | 4-Methyl-α-methyltryptamine | 20–60 mg+ | Unknown | |
| 5-Fluoro-AMT | 5-Fluoro-α-methyltryptamine | 25 mg+ | >9 hours | |
| 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 apsychedelic but is also astimulant andentactogen.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 psychedelicorally but to be much lesspotent 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:[29][30] | ||||
| 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-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-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-MeO-DiPT | 6-Methoxy-N,N-diisopropyltryptamine | >50 mg | Unknown | |
| 6-MeO-MiPT | 6-Methoxy-N-methyl-N-isopropyltryptamine | >50 mg | 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:a5-Bromo-DMT is active viasmoking at a dose of 20 to 50 mg.b =Bretisilocin is activeintravenously with a dose range of 10 to 20 mg and aduration of 60 to 90 minutes.c =5-MeS-DMT's oral dose and duration are unknown, butsmoked the dose is 15 to 30 mg and the duration is <1 hour.Refs:[3][4][2][9][11]Individual:[31][32] | ||||
| 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 | |
| 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[33] | 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[34] | 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[35] | 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[36] | 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[36] | 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 | ||
| 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 | ||
| 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[37] | 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-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[38] | artificial | 4-OH | CH3 | H2C=CH-CH2 | 4-hydroxy-N-Methyl-N-allyltryptamine | ||
| 4-AcO-MALT[39] | artificial | 4-OCOCH3 | CH3 | H2C=CH-CH2 | 4-acetoxy-N-Methyl-N-allyltryptamine | ||
| 4-HO-NALT[40] | artificial | 4-OH | H | H2C=CH-CH2 | 4-hydroxy-N-allyltryptamine | ||
| 4-HO-MsBT | artificial | 4-OH | CH(CH3)CH2CH3 | CH3 | 4-hydroxy-N-sec-butyl-N-methyltryptamine | ||
| 4-HO-EiBT | artificial[41] | 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[42] | 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[43] | 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[44] | 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[45] | 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[46] | artificial | 5-OCF3 | CH3 | CH3 | 5-(trifluoromethoxy)-N,N-dimethyltryptamine | ||
| 5-Nitro-DMT[47] | 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[48] | 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[49] | 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 | 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[50] | 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 # |
α-Alkyltryptamines are a group of substituted tryptamines which possess analkyl group, such as amethyl orethyl group, attached at thealpha carbon, and in most cases no substitution on theamine nitrogen.[51][52][53] α-Alkylation oftryptamine makes it much moremetabolically stable and resistant to degradation bymonoamine oxidase, resulting in increasedpotency and greatly lengthenedhalf-life.[53] This is analogous to α-methylation ofphenethylamine intoamphetamine.[53]
Many α-alkyltryptamines aredrugs, acting asmonoamine releasing agents, non-selectiveserotonin receptor agonists, and/ormonoamine oxidase inhibitors,[54][55][56][57] and producepsychostimulant,entactogen, and/orpsychedelic effects.[51][52][53] The most well-known of these agents areα-methyltryptamine (αMT) andα-ethyltryptamine (αET), both of which were used clinically asantidepressants for a brief period of time in the past and areabused asrecreational drugs.[52][53] In accordance with its action as a dualreleasing agent ofserotonin anddopamine, αET has been found to produceserotonergicneurotoxicity similarly toamphetamines likeMDMA andPCA, 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.[58]
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
| Tryptophan | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid | 73-22-3 | |
| 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 | |
| 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[59] | 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[60] | 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[61] | (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[35][62] | 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine | ||
| BK-NM-AMT (α,N-dimethyl-β-ketotryptamine)[63][64][65] | 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one | ||
| BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine)[66][67][68][65] | 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one | ||
| BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[68][69][70] | 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one | ||
| BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine)[68][71][72] | 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one |
A number ofβ-ketotryptamines (beta-ketotryptamines) are known.[63][65][68] These compounds are α-alkyl-β-ketotryptamines and are analogous to thecathinones (β-ketoamphetamines) of the relatedphenethylamine family. Known β-ketotryptamines includeBK-NM-AMT,BK-5F-NM-AMT,BK-5Cl-NM-AMT, andBK-5Br-NM-AMT.[63][65][68] They act asmonoamine releasing agents.[63][65][68]
Examples ofcyclized tryptamines include:
Other closely related cyclized tryptamine-like compounds include the following:
A number of related compounds are known, with a similar structure but having theindole core flipped (isotryptamines) and/or replaced with related cores such asindene,indoline,indazole,indolizine,benzothiophene, orbenzofuran. Like tryptamines, these related compounds are primarily active as agonists at the 5-HT2 family of serotonin receptors, with applications in the treatment ofglaucoma,cluster headaches, or asanorectics.
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
| C-DMT[73] | 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 | |
| (S)-5,6-Difluoro-isoAMT[74] | (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[75][76] | 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine | ||
| Example 1[77] | 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[78] | (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine | 478132-12-6 | |
| Example 3[79] | (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine | 890087-75-9 | |
| Example 1[80] | (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[81] | (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine | 748116-94-1 | |
| I-32[82] | 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol | ||
| 2-Azapsilocin (Psilocin indazole analogue,P-6)[83] | 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[84] | 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 | |
| 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 |
Table 4 Human potency data for selected hallucinogens. [...]
{{cite conference}}: CS1 maint: bot: original URL status unknown (link)Doses for vaporized or inhaled free-base DMT are typically 40–50 mg, although larger doses have been reported (100 mg; Shulgin and Shulgin 1997). Pallavicini et al. (2021) have reported that vaporization of approximately 40 mg of DMT, administered in a natural setting, produced potential electroencephalographic markers of mystical-type experiences in 35 volunteers. The onset of effects for inhaled DMT is rapid, similar to that of IV administration, but lasts less than 30 min (Riba et al. 2015; Davis et al. 2020). [...] For administration of pharmahuasca, 50 mg DMT:100 mg harmaline is usually the recommended dosage. However, combinations of 50 mg harmaline:50 mg harmine and 50 mg DMT have been tested with success. The harmalas and DMT are typically put into separate gelatin capsules, with the harmaline/harmine being taken first and the DMT being taken 15 to 20 min later. The use of moclobemide, a reversible inhibitor of MAO-A, has also been reported in DMT "pharmahuasca" studies (Kaasik et al. 2020; Ruffell et al. 2020).
Recent studies tested i.v. DMT with different administration regimens. Such protocols entailed 0–19.2 mg bolus 0.5–0.8 mg/min constant infusion of DMT freebase (as hemifumarate) for up to 90 min (Basel) [7], 11.2 mg bolus 1.2 mg/min infusion of DMT freebase (as fumarate) for up to 30 min (London) [8], and constant infusion totaling 13.4 mg DMT freebase (as fumarate) over 10 min (London) [110]). [...] The various β-carbolines in B. caapi, especially harmine and harmaline, enable the attainment of sufficient plasma DMT concentrations to evoke psychedelic effects lasting 4–6 h [5, 61].
Since the β-carbolines per se could not explain the legendary psychoptic (visionary) activity of the jungle ambrosia, this had to be due to its DMT content, which amounted to an average of 29 mg/dose in the 16 potions analyzed (range: 25-36 mg/dose). [...] TABLE 1 Human Pharmacology of Psychoptic Tryptamines [...]
Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.
The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.
Szara and co-workers (221,223,225) noted psychotomimetic activity for N,N-diethyltryptamine (DET; 38) at a dose of 1 mg/kg. [...] N,N-Dipropyltryptamine (DPT; 39) is also hallucinogenic in man at 1 mg/kg (222). [...] Branching of the propyl groups results in N,N-diisopropyltryptamine (DIPT; 40), which is orally active at 20 to 50 mg (202). N,N-Dibutyltryptamine (DBT; 41) and N,N-dihexyltryptamine (DHT; 42) have been examined only briefly. At 1 mg/kg, DBT produced only slight perceptual, emotional, and thinking disturbances in man, while DHT at the same dose was completely inactive (222).
4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84].
[Morris:] Bufotenine is a drug that I have tried. I've tried isolated pure bufotenine and it is a psychedelic that is both pharmacologically and experientially and chemically intermediate between DMT and 5-MeO-DMT. So it has a longer duration than actually both 5-MeO-DMT and DMT. It's yet less visual than DMT but more visual than 5-MeO-DMT, so it's kind of like in-between the two. It's also very nauseating, which is the main reason that people seem not to enjoy it very much. But it is a classical psychedelic drug that produces visionary effects. And Jonathan Ott actually liked the effect of it quite a bit.
[Morris:] I've used [bufotenine] a couple times, once at 50 milligrams of the freebase snorted. [...] I found it to be extremely nauseating. I found it to be qualitatively intermediate between 5-MeO-DMT and DMT in that it was more visual than my experiences with 5-MeO-DMT but less visual than my typical experiences with DMT. It had a longer duration than 5-MeO-DMT and maybe even a longer duration than DMT as well. It was about an hour. Although I don't have all that much experience snorting DMT freebase.
[...] [Hartsel:] The α,N,N-Dimethyl[tryptamine]. [Morris:] Oh yeah, I've made it and tried it actually. [Hartsel:] Oh you did? [Morris:] Yeah, yeah. [Hartsel:] Oh, well what did it do? [Morris:] It is active, it's an active psychedelic. It's reduced potency. I never got it to a dose where it produced particularly interesting effects. I can look up the exact dose. I think it was like... the only thing I remember is that I felt like it was making me sneeze a lot. But it was very pleasant. Nothing bad happened. But the dose just wasn't high enough. I think I took maybe 40 mg. So it was much less potent than AMT orally. The other issue of course is that it could be a prodrug ofN-methyl-AMT, which is active, or AMT itself maybe. [...]
{{cite journal}}: CS1 maint: multiple names: authors list (link)Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e., S(+)-5,6-difluoro-α-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best, only 10-fold.