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.

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).

Use and effects The doses, potencies, durations, and effects of psychedelic tryptamines have been reviewed by Alexander Shulgin and other authors.

Ring-unsubstituted tryptamines

+ Compound Chemical name Dose Duration Tryptamine (T) Tryptamine >100 mga – NMT N-Methyltryptamine Unknownb – NET N-Ethyltryptamine Unknown Unknown NPT N-Propyltryptamine 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 250mg with a very short duration. b = NMT is not orally active, but is said to be active smoked at a dose of 50 to 120mg with a duration of seconds to minutes. Also reportedly orally active with an . c = DMT is active parenterally at doses of 50 to 100mg (2–100mg) smoked, intramuscularly, or subcutaneously and at doses of 4 to 30mg intravenously (bolus), with a duration of <1 hour or 5–20minutes. For continuous intravenous infusion, the dose is 0.6 to 2.4mg/minute. Also orally active with an (as in ayahuasca or pharmahuasca), with a typical dose of 50mg (range 20–120mg) and a duration of 4 to 6hours. d = Mor-T was inactive at a dose of 30mg by intramuscular injection. Refs: Individual:

4-Hydroxytryptamines

+ 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 10–30 mg 3–8 hours 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 40mg with an average duration of 3.6hours. Refs: Individual:

5-Hydroxytryptamines

+ 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 5-HO-MET 5-Hydroxy-N-methyl-N-ethyltryptamine 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 16mg with a duration of 1 to 2hours and is active via insufflation and other parenteral routes. Refs: Individual:

5-Methoxytryptamines

+ 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-MsBT 5-Methoxy-N-methyl-N-sec-butyltryptamine 10–30 mg 3–4 hours 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 3mg intravenously, with a duration of 5 to 20minutes. Also orally active with an at doses of 10 to 25mg. b = Melatonin is not a psychedelic but a hypnotic and is non-hallucinogenic at doses of up to 1,200mg. Refs: Individual:

α-Alkyltryptamines

+ 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: Individual:

Other tryptamines