Substituted tryptamine explained

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).

Use and effects

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

Ring-unsubstituted tryptamines

Compound Chemical name Dose Duration
Tryptamine (T) Tryptamine >100 mga –
N-Methyltryptamine Unknownb –
N-Ethyltryptamine Unknown Unknown
N-Isopropyltryptamine Unknown Unknown
N-sec-Butyltryptamine 25–75 mg "Short"
N-tert-Butyltryptamine 5–20 mg Unknown
N-Amyltryptamine >100 mg –
N-Hexyltryptamine >100 mg –
N,N-Dimethyltryptamine >350–1,000 mgc –
N,N-Diethyltryptamine 50–150 mg 2–4 hours
N,N-Dipropyltryptamine 100–250 mg 2–4 hours
N,N-Diisopropyltryptamine 25–100 mg (15–150 mg+) 4–8 hours
N,N-Diallyltryptamine 60–80 mg <3 hours
N,N-Dibutyltryptamine ≥100 mg Unknown
N,N-Diamyltryptamine Unknown Unknown
N,N-Dihexyltryptamine >100 mg –
N-Methyl-N-ethyltryptamine 80–100 mg Unknown
N-Methyl-N-propyltryptamine >50 mg Unknown
N-Methyl-N-isopropyltryptamine 10–25 mg 3–4 hours
N-Methyl-N-allyltryptamine 25–50 mg Unknown
N-Methyl-N-butyltryptamine 250–400 mg 4–6 hours
N-Methyl-N-sec-butyltryptamine 250–400 mg Unknown
N-Ethyl-N-propyltryptamine Unknown Unknown
N-Ethyl-N-isopropyltryptamine 24–40 mg 4–6 hours
N-Propyl-N-isopropyltryptamine Unknown Unknown
N,N-Tetramethylenetryptamine Unknown Unknown
N,N-Pentamethylenetryptamine Unknown Unknown
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: [11] [12] [13] [14] [15] [16] [17] [18] [19] [20] [21]

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-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-Hydroxy-N,N-dibutyltryptamine >20 mg Unknown
4-Hydroxy-N,N-diisobutyltryptamine >20 mg Unknown
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-Hydroxy-N-methyl-N-tert-butyltryptamine >15 mg Unknown
4-HO-EPT (eprocin) 4-Hydroxy-N-ethyl-N-propyltryptamine Unknown Unknown
4-Hydroxy-N-ethyl-N-isopropyltryptamine Unknown Unknown
4-HO-PiPT (piprocin) 4-Hydroxy-N-propyl-N-isopropyltryptamine Unknown Unknown
4-Hydroxy-N,N,N-trimethyltryptamine Unknown Unknown
Aeruginascin (4-PO-TMT) 4-Phosphoryloxy-N,N,N-trimethyltryptamine Unknown Unknown
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: [22] [23] [24]

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-Hydroxy-N,N-diethyltryptamine Unknown Unknown
5-HO-DPT (DiPS, NDPS) 5-Hydroxy-N,N-dipropyltryptamine Unknown Unknown
5-Hydroxy-N,N-diisopropyltryptamine Unknown Unknown
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: [25] [26] [27] [28]

5-Methoxytryptamines

Compound Chemical name Dose Duration
5-MT (5-MeO-T) 5-Methoxytryptamine Unknown Unknown
5-Methoxy-N-methyltryptamine Unknown Unknown
5-Methoxy-N-ethyltryptamine Unknown Unknown
5-Methoxy-N-isopropyltryptamine Unknown Unknown
5-MeO-DMT (mebufotenin) 5-Methoxy-N,N-dimethyltryptamine >35 mga –
5-Methoxy-N,N-diethyltryptamine 1–3 mg 3–4 hours
5-Methoxy-N,N-dipropyltryptamine 6–10 mg 2–4 hours
5-Methoxy-N,N-diisopropyltryptamine 6–12 mg 4–8 hours
5-Methoxy-N,N-diallyltryptamine 12–25 mg 2–4 hours
5-Methoxy-N,N-dibutyltryptamine Unknown Unknown
5-Methoxy-N,N-di-sec-butyltryptamine Unknown Unknown
5-Methoxy-N-methyl-N-ethyltryptamine Unknown Unknown
5-Methoxy-N-methyl-N-propyltryptamine Unknown Unknown
5-Methoxy-N-methyl-N-isopropyltryptamine 4–6 mg (0.5–20 mg+) 4–6 hours
5-Methoxy-N-methyl-N-allyltryptamine Unknown Unknown
5-Methoxy-N-methyl-N-sec-butyltryptamine 10–30 mg 3–4 hours
5-Methoxy-N-ethyl-N-propyltryptamine Unknown Unknown
5-Methoxy-N-ethyl-N-isopropyltryptamine Unknown Unknown
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-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: [29]

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-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
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: [30] [31]

Other tryptamines

Compound Chemical name Dose Duration
Lespedamine (1-MeO-DMT) 1-Methoxy-N,N-dimethyltryptamine Unknown Unknown
2-Methyl-N,N-dimethyltryptamine 50–100 mg 4–6 hours
2-Methyl-N,N-diethyltryptamine 80–120 mg 6–8 hours
4-Methoxy-N,N-dimethyltryptamine Unknown Unknown
4-Methoxy-N,N-diethyltryptamine >30 mg Unknown
4-Methoxy-N,N-diisopropyltryptamine Unknown Unknown
4-Methoxy-N-methyl-N-isopropyltryptamines 20–30 mg 4–6 hours
4,5-Methylenedioxy-N,N-dimethyltryptamine Unknown Unknown
4,5-Methylenedioxy-N,N-diisopropyltryptamine >25 mg Unknown
5-Fluoro-N,N-dimethyltryptamine Unknown Unknown
5-Chloro-N,N-dimethyltryptamine Unknown Unknown
5-Bromo-N,N-dimethyltryptamine Unknowna Unknown
Bretisilocin (5-fluoro-MET) 5-Fluoro-N-methyl-N-ethyltryptamine Unknownb Unknownb
5-Methoxy-2-methyl-N,N-dimethyltryptamine 75–150 mg 5–10 hours
5-Methylthio-N,N-dimethyltryptamine Unknownc Unknownc
5,6-Dimethoxy-N-methyl-N-isopropyltryptamine >75 mg Unknown
5,6-Methylenedioxy-N,N-dimethyltryptamine >5 mg Unknown
5,6-Methylenedioxy-N,N-diisopropyltryptamine Unknown Unknown
5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine >50–60 mg Unknown
6-Fluoro-N,N-dimethyltryptamine Unknown Unknown
6-Fluoro-N,N-diethyltryptamine >80 mg Unknown
6-Hydroxy-N,N-dimethyltryptamine >80 mg Unknown
6-Hydroxy-N,N-diethyltryptamine ≥10 mgd 3–4 hoursd
6-Methoxy-N,N-dimethyltryptamine Unknown Unknown
6-Methoxy-N,N-diisopropyltryptamine >50 mg Unknown
6-Methoxy-N-methyl-N-isopropyltryptamine >50 mg Unknown
7-Hydroxy-N,N-dimethyltryptamine Unknown Unknown
7-Methoxy-N,N-dimethyltryptamine Unknown Unknown
7-Methoxy-N,N-diisopropyltryptamine >70 mg Unknown
7-Methoxy-N-methyl-N-isopropyltryptamine >70 mg Unknown
Footnotes: a = 5-Bromo-DMT is active via smoking at a dose of 20 to 50mg. b = Bretisilocin is active intravenously with a dose range of 10 to 20mg and a duration of 60 to 90minutes. c = 5-MeS-DMT's oral dose and duration are unknown, but smoked the dose is 15 to 30mg and the duration is 10 to 30minutes or <1 hour. d = Controversial and uncertain. Refs: Individual: [32] [33] [34]

Pharmacology

Pharmacodynamics

Compound SERT
269 447 117 380 380 112 257 – 2,090 275 69 2,400
372 191 98 339 200 25 245 – 447 79 87 2,570
5,250 – 195 – 851 479 3,090 – – 776 – –
977 – 871 417 692 25 631 – – 661 794 3,090
8.3 59 22 25 224 6.2 209 166 302 18 8.9 1,120
10 91 21 575 200 15 490 – 589 25 4.4 –
170 – 871 – 324 46 – – – 2,190 – –
17 1,020 54 977 457 100 2,240 – – 162 60 4,470
54 1,170 174 – 1,622 98 – – – 407 661 5,620
5.9 21 3.5 135 8.5 5.5 17 – 1.8 16 8.5 –
Compound SERT
>10,000 >10,000 93 456 2,323 108 335 >10,000 611 487 883 3,742
32 854 619 2,338 2,579 42 1,567 >10,000 4,373 4,543 284 157
121 >10,000 3,742 >10,000 >10,000 399 >10,000 >10,000 >10,000 >10,000 3,423 1,258
63 305 19 44 340 4.7 141 >10,000 70 72 72 852
1.9 74 6.3 360 2,011 3,884 538 >10,000 277 36 3.9 2,032
132 5,137 1,718 >10,000 >10,000 163 >10,000 >10,000 >10,000 >10,000 1,231 2,531
12 303 23 3,496 448 59 2,186 >10,000 953 130 20 6,409
393 218 55 461 866 30 674 >10,000 961 26 41 145
200 >10,000 250 1,800 >10,000 ? 4,020 ? 10,450 60 145 >10,000
170 >10,000 290 520 >10,000 ? 1,810 ? 4,620 16 300 >10,000
>10,000 >10,000 >10,000 ? 14,142 ? >10,000 >10,000 ? ? ? 549
7.3 3.9 7.8 93 11 30 31 >10,000 9 6.9 6.6 >10,000

Chemistry

Synthesis

The chemical syntheses of numerous tryptamines have been described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved). A well-known and widely used synthetic approach for making tryptamines is the Speeter–Anthony route, which starts with indole.[35] [36] [37] Other tryptamine synthesis routes have also been described, for instance starting with tryptamine rather than indole. The chemical syntheses of the psychedelic tryptamines bufotenin (5-HO-DMT) and 5-MeO-DMT (mebufotenin) have been comprehensively reviewed.[38]

List of substituted tryptamines

StructureNameOriginRing sub.RN1RN2Chemical nameCAS #
Tryptamine (T) Animals, plants, fungi H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine 61-54-1
Plants H H CH3 N-methyltryptamine 61-49-4
Plants 2-OH H CH3 2-hydroxy-N-methyltryptamine 106987-89-7
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 H 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
Animals 5-OCH3, 6-OH H O=C-CH3 N-[2-(6-Hydroxy-5-methoxy-1''H''-indol-3-yl)ethyl]acetamide 2208-41-5
4-Hydroxytryptamine (4-HT) Fungi H H 4-hydroxytryptamine 570-14-9
Fungi H CH3 4-hydroxy-N-methyltryptamine 28363-70-4
Psilocin (4-HO-DMT) Fungi CH3 CH3 4-hydroxy-N,N-dimethyltryptamine 520-53-6
Fungi 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
Animals, plants H 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
Marine sponges, invertebrates 5-Br CH3 CH3 5-bromo-N,N-dimethyltryptamine 17274-65-6
Marine invertebrates 6-Br H H 6-bromotryptamine 96624-18-9
Marine invertebrates 5,6-Br H H 5,6-dibromotryptamine
Marine invertebrates 5,6-Br H CH3 5,6-dibromo-N-methyltryptamine
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
Marine invertebrates 2,4,6-Br, 1,7-OCH3 CH3 CH3 1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine 443356-86-3
1-Methyltryptamine (1-MT)artificial1-CH3HH1-Methyltryptamine7518-21-0
4-Methoxytryptamine (4-MeO-T)artificial4-OCH3HH4-Methoxytryptamine3610-35-3
4-Fluorotryptamine (4-FT)artificial4-FHH4-Fluorotryptamine?
5-Methyltryptamine (5-MT)artificial5-CH3HH5-Methyltryptamine1821-47-2
5-Fluorotryptamine (5-FT)artificial5-FHH5-Fluorotryptamine576-16-9
5-Chlorotryptamine (5-Cl-T)artificial5-ClHH5-Chlorotryptamine?
5-Bromotryptamine (5-Br-T)artificial5-BrHH5-Bromotryptamine?
6-Methyltryptamine (6-MT)artificial6-CH3HH6-Methyltryptamine?
6-Hydroxytryptamine (6-HT)artificial6-OHHH6-Hydroxytryptamine443-31-2
6-Methoxytryptamine (6-MeO-T)artificial6-OCH3HH6-Methoxytryptamine3610-36-4
6-Fluorotryptamine (6-FT)artificial6-FHH6-Fluorotryptamine575-85-9
7-Methyltryptamine (7-MT)artificial7-CH3HH7-Methyltryptamine?
7-Methoxytryptamine (7-MeO-T)artificial7-OCH3HH7-Methoxytryptamine?
7-Chlorotryptamine (7-Cl-T)artificial7-ClHH7-Chlorotryptamine3804-16-8
Acetryptine (5-AT)artificial5-COCH3HH5-Acetyltryptamine3551-18-6
5-PhO-Tartificial5-OC6H5HH5-Phenoxytryptamine31363-70-9
5-BTartificial5-OCH2C6H5HH5-Benzyloxytryptamine20776-45-8
5-CTartificial5-CONH2HH5-Carboxamidotryptamine74885-09-9
5-Nitrotryptamine (Nitro-I)artificial5-NO2HH5-Nitrotryptamine55747-72-3
artificial 5-O(CH2)8CH3 H H 5-Nonyloxytryptamine 157798-12-4
2-Methyl-5-hydroxytryptamineartificial2-CH3, 5-OHHH3-(2-aminoethyl)-2-methyl-1H-indol-5-ol78263-90-8
NETartificialHHCH2CH3N-ethyltryptamine61-53-0
NiPTartificialHHCH(CH3)2N-isopropyltryptamine14121-10-9
NcPTartificialHHC3H5N-cyclopropyltryptamine
NsBTartificialHHCH(CH3)CH2CH3N-sec-butyltryptamine
NtBTartificialHHC(CH3)3N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine1344092-44-9
NATartificialHH(CH2)4CH3N-[2-(1''H''-indol-3-yl)ethyl]pentan-1-amine
NHTartificialHH(CH2)5CH3N-[2-(1''H''-indol-3-yl)ethyl]hexan-1-amine
N-Benzyltryptamine (NBnT)artificialHHCH2C6H5N-benzyltryptamine15741-79-4
T-NBOMe (NBOMeT)artificialHHCH2C6H4(o-OCH3)N-(2-methoxybenzyl)tryptamine418781-81-4
4-HO-NETartificial4-OHCH2CH3H4-hydroxy-N-ethyltryptamine
4-HO-NPTartificial4-OHCH(CH3)2H4-hydroxy-N-propyltryptamine
4-HO-NiPTartificial4-OHCH(CH3)2H4-hydroxy-N-isopropyltryptamine
4-HO-NALT[39] artificial4-OHHH2C=CH-CH24-hydroxy-N-allyltryptamine
4-HO-NBT (4-HO-NnBT)artificial4-OHH(CH2)3CH34-hydroxy-N-n-butyltryptamine
4-HO-NiBTartificial4-OHHCH2CH(CH3)24-hydroxy-N-isobutyltryptamine
4-HO-NsBTartificial4-OHHCH(CH3)CH2CH34-hydroxy-N-sec-butyltryptamine
4-HO-NtBTartificial4-OHHC(CH3)34-hydroxy-N-tert-butyltryptamine
4-HO-NBnTartificial4-OHHCH2C6H54-hydroxy-N-benzyltryptamine
4-HO-NcHTartificial4-OHHC6H114-hydroxy-N-cyclohexyltryptamine
5-MeO-NETartificial5-OCH3HCH2CH35-methoxy-N-ethyltryptamine1019-46-1
5-MeO-NiPTartificial5-OCH3HCH(CH3)25-methoxy-N-isopropyltryptamine109921-55-3
5-MeO-NsBTartificial5-OCH3HCH(CH3)CH2CH35-methoxy-N-sec-butyltryptamine
5-MeO-NBnTartificial5-OCH3HCH2C6H55-methoxy-N-benzyltryptamine25100-31-6
5-MeO-T-NBOMeartificial5-OCH3HCH2C6H4(o-OCH3)5-methoxy-N-(ortho-methoxybenzyl)tryptamine1335331-37-7
5-MeO-T-NB3OMe [40] artificial5-OCH3HCH2C6H4(m-OCH3)5-methoxy-N-(meta-methoxybenzyl)tryptamine1648553-42-7
5-MeO-NBpBrTartificial5-OCH3HCH2C6H4(p-Br)N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine155639-13-7
5-MeO-34MPEMT [41] artificial5-OCH3CH3CH2CH2C6H3(p,m-OCH3)N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
Idalopirdineartificial6-FHCH2C6H4(m-OCH2CF2CF2H)2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine467459-31-0
Z2876442907[42] artificial4-CH3HCH2(C3HNS)-COOCH2CH3ethyl 2-(methyl)-1,3-thiazole-5-carboxylate
Cis-2',5'-dimethyl-4-HO-azt-T [43] artificial 4-OH cis-(CHCH3)CH2(CHCH3) 3--1H-indol-4-ol
artificial H (CH2)4 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole 14008-96-9
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 artificial 4-OH cis-(CHCH3)CH2CH2(CHCH3) 3--1H-indol-4-ol
artificial 5-OCH3 (CH2)4 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole 3949-14-2
artificial 4-F-5-OCH3 (CH2)4 4-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole 344790-93-8
artificial H (CH2)5 3-(2-Piperidin-1-ylethyl)-1H-indole 26628-87-5
artificial 5-OCH3 (CH2)5 5-Methoxy-3-(2-piperidin-1-ylethyl)-1H-indole
artificial H ? 3-[2-(Morpholin-4-yl)ethyl]-1H-indole 25262-59-3
artificial 5-OCH3 ? 5-Methoxy-3-[2-(morpholin-4-yl)ethyl]-1H-indole 3949-13-1
IsoqT[44] artificial H ? 3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-1H-indole
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
METartificialHCH3CH2CH3N-Methyl-N-ethyltryptamine5599-69-9
MPTartificialHCH3CH2CH2CH3N-Methyl-N-propyltryptamine850032-72-3
MiPTartificialHCH3CH(CH3)2N-Methyl-N-isopropyltryptamine96096-52-5
McPTartificialHCH3C3H5N-Methyl-N-cyclopropyltryptamine1373918-63-8
EcPTartificialHCH2CH3C3H5N-ethyl-N-cyclopropyltryptamine
PcPTartificialHCH2CH2CH3C3H5N-propyl-N-cyclopropyltryptamine
iPcPTartificialHCH(CH3)2C3H5N-isopropyl-N-cyclopropyltryptamine
DcPTartificialHC3H5C3H5N,N-dicyclopropyltryptamine1373918-62-7
MBTartificialHCH3(CH2)3CH3N-Methyl-N-butyltryptamine848130-12-1
MsBTartificialHCH3CH(CH3)CH2CH3N-Methyl-N-sec-butyltryptamine
MiBTartificialHCH3CH2CH(CH3)2N-Methyl-N-iso-butyltryptamine
McPMTartificialHCH3CH2C3H5N-Methyl-N-(cyclopropylmethyl)tryptamine
Deudimethyltryptamine (DMT-d10; likely CYB004)artificialHCH3CH3α,α,β,β-Tetradeutero-N,N-bis(trideuteriomethyl)tryptamine2742678-60-8
SPL028 (D2-DMT)artificialHCH3CH3α,α-Dideutero-N,N-dimethyltryptamine?
DETartificialHCH2CH3CH2CH3N,N-diethyltryptamine61-51-8
EPTartificialHCH2CH3CH2CH2CH3N-Ethyl-N-propyltryptamine850032-68-7
EiPTartificialHCH2CH3CH(CH3)2N-Ethyl-N-isopropyltryptamine848130-11-0
DPTartificialHCH2CH2CH3CH2CH2CH3N,N-dipropyltryptamine61-52-9
PiPTartificialHCH2CH2CH3CH(CH3)2N-Propyl-N-isopropyltryptamine1354632-00-0
DiPTartificialHCH(CH3)2CH(CH3)2N,N-diisopropyltryptamine14780-24-6
EBTartificialHCH2CH3(CH2)3CH3N-ethyl-N-butyltryptamine
PBTartificialHCH2CH2CH3(CH2)3CH3N-propyl-N-butyltryptamine
iPsBTartificialHCH(CH3)2CH(CH3)CH2CH3N-isopropyl-N-sec-butyltryptamine
DBTartificialH(CH2)3CH3(CH2)3CH3N,N-dibutyltryptamine15741-77-2
DiBTartificialHCH2CH(CH3)2CH2CH(CH3)2N,N-diisobutyltryptamine63938-64-7
DsBTartificialHCH(CH3)CH2CH3CH(CH3)CH2CH3N,N-disecbutyltryptamine
DATartificialH(CH2)4CH3(CH2)4CH3N,N-diamyltryptamine
DHTartificialH(CH2)5CH3(CH2)5CH3N,N-dihexyltryptamine
MALTartificialHCH3H2C=CH-CH2N-methyl-N-allyltryptamine1366416-29-6
DALTartificialHH2C=CH-CH2H2C=CH-CH2N,N-diallyltryptamine60676-77-9
PALTartificialHH2C=CH-CH2CH2CH2CH3N-propyl-N-allyltryptamine2686297-71-0
iPALT (ALiPT)artificialHH2C=CH-CH2CH(CH3)2N-allyl-N-isopropyltryptamine
N-DEAOP-NMTartificialH?CH3N-(3-diethylamino-3-oxopropyl)-N-methyltryptamine
5-MeO-N-DEAOP-NMTartificial5-OCH3?CH3N-(3-diethylamino-3-oxopropyl)-N-methyl-5-methoxytryptamine
N-DEAOP-NET[45] artificialH?CH2CH3N-(3-diethylamino-3-oxopropyl)-N-ethyltryptamine
5-MeO-N-DEAOP-NETartificial5-OCH3?CH2CH3N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-methoxytryptamine
1-Methyl-DMTartificial1-CH3CH3CH31-methyl-N,N-dimethyltryptamine13366-47-7
2-Methyl-DMTartificial2-CH3CH3CH3(2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine1080-95-1
2-Methyl-DETartificial2-CH3CH2CH3CH2CH3N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine26628-88-6
2-Methyl-DiPTartificial2-CH3CH(CH3)2CH(CH3)22-methyl-N,N-diisopropyltryptamine
2-Methyl-iPALTartificial2-CH3CH(CH3)2H2C=CH-CH22-methyl-N-isopropyl-N-allyltryptamine2915652-49-0
4-Amino-DMT [46] artificial4-NH2CH3CH34-amino-N,N-dimethyltryptamine60331-61-5
4-Methyl-DMTartificial4-CH3CH3CH34,N,N-trimethyltryptamine28289-23-8
4-MeO-DMTartificial4-OCH3CH3CH34-methoxy-N,N-dimethyltryptamine3965-97-7
4-MeO-DETartificial4-OCH3CH2CH3CH2CH34-methoxy-N,N-diethyltryptamine
4-MeO-MiPTartificial4-OCH3CH3CH(CH3)24-methoxy-N-methyl-N-isopropyltryptamine96096-53-6
4-MeO-DiPTartificial4-OCH3CH(CH3)2CH(CH3)24-methoxy-N,N-diisopropyltryptamine
Deupsilocin (d10-psilocin; likely CYB003)artificial4-OHCH3CH34-Hydroxy-α,α,β,β-Tetradeutero-N,N-bis(trideuteriomethyl)tryptamine1435934-64-7
4-AcO-DMT (psilacetin)artificial4-OCOCH3CH3CH34-acetoxy-N,N-dimethyltryptamine92292-84-7
4-PrO-DMTartificial4-OCOCH2CH3CH3CH34-propionyloxy-N,N-dimethyltryptamine1373882-11-1
4-GO-DMT (RE109; FT-109)artificial4-OCO(CH2)3COOHCH3CH34-glutaryloxy-N,N-dimethyltryptamine
4-HO-MET (metocin)artificial4-OHCH3CH2CH34-hydroxy-N-methyl-N-ethyltryptamine77872-41-4
4-AcO-METartificial4-OCOCH3CH3CH2CH34-acetoxy-N-methyl-N-ethyltryptamine1445751-40-5
4-PrO-METartificial4-OCOCH2CH3CH3CH2CH34-propionyloxy-N-methyl-N-ethyltryptamine
4-PO-METartificial4-OPO3H2CH3CH2CH34-phosphoryloxy-N-methyl-N-ethyltryptamine
4-HO-DET (ethocin)artificial4-OHCH2CH3CH2CH34-hydroxy-N,N-diethyltryptamine22204-89-3
4-AcO-DETartificial4-OCOCH3CH2CH3CH2CH34-acetoxy-N,N-diethyltryptamine1135424-15-5
4-PO-DET (ethocybin)artificial4-OPO3H2CH2CH3CH2CH34-phosphoryloxy-N,N-diethyltryptamine60480-02-6
4-HO-EPTartificial4-OHCH2CH3CH2CH2CH34-hydroxy-N-ethyl-N-propyltryptamine2595431-59-5
4-AcO-EPTartificial4-OCOCH3CH2CH3CH2CH2CH34-acetoxy-N-ethyl-N-propyltryptamine2750249-90-0
4-PO-EPTartificial4-OPO3H2CH2CH3CH2CH2CH34-phosphoryloxy-N-ethyl-N-propyltryptamine
4-AcO-EiPTartificial4-OCOCH3CH2CH3CH(CH3)24-acetoxy-N-ethyl-N-isopropyltryptamine
4-HO-MPTartificial4-OHCH3CH2CH2CH34-hydroxy-N-methyl-N-propyltryptamine763035-03-6
4-AcO-MPTartificial4-OCOCH3CH3CH2CH2CH34-acetoxy-N-methyl-N-propyltryptamine2173386-55-3
4-HO-MiPTartificial4-OHCH(CH3)2CH34-hydroxy-N-isopropyl-N-methyltryptamine77872-43-6
4-AcO-MiPTartificial4-OCOCH3CH3CH(CH3)24-acetoxy-N-methyl-N-isopropyltryptamine1024612-25-6
4-HO-MALT[47] artificial4-OHCH3H2C=CH-CH24-hydroxy-N-methyl-N-allyltryptamine
4-AcO-MALT[48] artificial4-OCOCH3CH3H2C=CH-CH24-acetoxy-N-Methyl-N-allyltryptamine
4-HO-iPALTartificial4-OHCH(CH3)2H2C=CH-CH24-hydroxy-N-isopropyl-N-allyltryptamine
4-HO-MBTartificial4-OH(CH2)3CH3CH34-hydroxy-N-butyl-N-methyltryptamine
4-HO-MsBTartificial4-OHCH(CH3)CH2CH3CH34-hydroxy-N-sec-butyl-N-methyltryptamine
4-HO-MtBTartificial4-OHC(CH3)3CH34-hydroxy-N-tert-butyl-N-methyltryptamine
4-HO-EiBTartificial[49] 4-OHCH2CH(CH3)2CH2CH34-hydroxy-N-iso-butyl-N-ethyltryptamine
4-HO-McPTartificial4-OHC3H5CH34-hydroxy-N-cyclopropyl-N-methyltryptamine2883663-05-4
4-AcO-McPTartificial4-OCOCH3C3H5CH34-acetoxy-N-cyclopropyl-N-methyltryptamine
4-HO-McPeTartificial4-OHC5H9CH34-hydroxy-N-cyclopentyl-N-methyltryptamine77872-48-1
4-HO-McPMT [50] artificial4-OHCH2C3H5CH34-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
4-HO-DPTartificial4-OHCH2CH2CH3CH2CH2CH34-hydroxy-N,N-dipropyltryptamine63065-88-3
4-AcO-DPTartificial4-OCOCH3CH2CH2CH3CH2CH2CH34-acetoxy-N,N-dipropyltryptamine1445751-75-6
4-HO-PiPTartificial4-OHCH2CH2CH3CH(CH3)24-hydroxy-N-propyl-N-isopropyltryptamine
4-AcO-PiPTartificial4-OCOCH3CH2CH2CH3CH(CH3)24-acetoxy-N-propyl-N-isopropyltryptamine
4-HO-DiPTartificial4-OHCH(CH3)2CH(CH3)24-hydroxy-N,N-diisopropyltryptamine132328-45-1
4-AcO-DiPTartificial4-OCOCH3CH(CH3)2CH(CH3)24-acetoxy-N,N-diisopropyltryptamine936015-60-0
4-PrO-DiPTartificial4-OCOCH2CH3CH(CH3)2CH(CH3)24-propionyloxy-N,N-diisopropyltryptamine1373882-13-3
Luvesilocin (RE104; FT-104)artificial4-OCO(CH2)3COOHCH(CH3)2CH(CH3)24-glutaryloxy-N,N-diisopropyltryptamine
4-PO-DiPTartificial4-OPO3H2CH(CH3)2CH(CH3)24-phosphoryloxy-N,N-diisopropyltryptamine1373882-09-7
4-HO-DALTartificial4-OHH2C=CH-CH2H2C=CH-CH24-hydroxy-N,N-diallyltryptamine2173386-70-2
4-AcO-DALTartificial4-OCOCH3H2C=CH-CH2H2C=CH-CH24-acetoxy-N,N-diallyltryptamine1445751-71-2
4-HO-DBTartificial4-OH(CH2)3CH3(CH2)3CH34-hydroxy-N,N-dibutyltryptamine63065-89-4
4-HO-DiBTartificial4-OHCH2CH(CH3)2CH2CH(CH3)24-hydroxy-N,N-diisobutyltryptamine
4-HO-DsBTartificial4-OHCH(CH3)CH2CH3CH(CH3)CH2CH34-hydroxy-N,N-disecbutyltryptamine127507-01-1
4-Fluoro-DMTartificial4-FCH3CH34-fluoro-N,N-dimethyltryptamine1644-64-0
5-MeO-DMT-d4 (α,α,β,β-tetradeutero-5-MeO-DMT)artificial5-OCH3CH3CH3α,α,β,β-Tetradeutero-5-methoxy-N,N-dimethyltryptamine66521-37-7
5-MeO-METartificial5-OCH3CH2CH3CH35-methoxy-N-methyl-N-ethyltryptamine16977-53-0
5-MeO-DETartificial5-OCH3CH2CH3CH2CH35-methoxy-N,N-diethyltryptamine2454-70-8
5-MeO-MPTartificial5-OCH3CH3CH2CH2CH35-methoxy-N-methyl-N-propyltryptamine
5-MeO-EPTartificial5-OCH3CH2CH3CH2CH2CH35-methoxy-N-ethyl-N-propyltryptamine850032-67-6
5-MeO-DPTartificial5-OCH3CH2CH2CH3CH2CH2CH35-methoxy-N,N-dipropyltryptamine69496-75-9
5-MeO-MALTartificial5-OCH3H2C=CH-CH2CH35-methoxy-N-Methyl-N-allyltryptamine1373918-64-9
5-MeO-DALTartificial5-OCH3H2C=CH-CH2H2C=CH-CH25-methoxy-N,N-diallyltryptamine928822-98-4
ASR-3001 (5-MeO-iPALT)artificial5-OCH3H2C=CH-CH2CH2CH(CH3)25-methoxy-N-allyl-N-isopropyltryptamine
5-MeO-MiPTartificial5-OCH3CH3CH(CH3)25-methoxy-N,N-methylisopropyltryptamine96096-55-8
5,6-MeO-MiPTartificial5-OCH3, 6-OCH3CH3CH(CH3)25,6-dimethoxy-N,N-methylisopropyltryptamine
5-MeO-MBTartificial5-OCH3CH3(CH2)3CH35-methoxy-N-methyl-N-butyltryptamine
5-MeO-MsBTartificial5-OCH3CH3CH(CH3)CH2CH35-methoxy-N-methyl-N-sec-butyltryptamine
5-MeO-McPTartificial5-OCH3CH3C3H55-methoxy-N-methyl-N-cyclopropyltryptamine
5-MeO-McBTartificial5-OCH3CH3C4H75-methoxy-N-methyl-N-cyclobutyltryptamine
5-MeO-EiPTartificial5-OCH3CH2CH3CH(CH3)25-methoxy-N-ethyl-N-isopropyltryptamine850032-66-5
5-MeO-PiPTartificial5-OCH3CH2CH2CH3CH(CH3)25-methoxy-N-propyl-N-isopropyltryptamine
5-MeO-DiPTartificial5-OCH3CH(CH3)2CH(CH3)25-methoxy-N,N-diisopropyltryptamine4021-34-5
5-MeO-DBTartificial5-OCH3(CH2)3CH3(CH2)3CH35-methoxy-N,N-dibutyltryptamine73785-42-9
5-MeO-DsBTartificial5-OCH3CH(CH3)CH2CH3CH(CH3)CH2CH35-methoxy-N,N-di-sec-butyltryptamine
5-MeS-DMTartificial 5-SCH3 CH3 CH3 5-methylthio-N,N-dimethyltryptamine 5102-11-4
5-AcO-DMT (O-acetylbufotenine)artificial5-OCOCH3CH3CH35-acetoxy-N,N-dimethyltryptamine16977-50-7
5-t-BuCO-DMT (O-pivalylbufotenine)artificial?CH3CH35-pivaloxy-N,N-dimethyltryptamine?
5-AcO-MET [51] artificial5-OCOCH3CH3CH2CH35-acetoxy-N-methyl-N-ethyltryptamine
5-AcO-DETartificial5-OCOCH3CH2CH3CH2CH35-acetoxy-N,N-diethyltryptamine
5-AcO-EPT [52] artificial5-OCOCH3CH2CH3CH2CH2CH35-acetoxy-N-ethyl-N-propyltryptamine
5-AcO-DPTartificial5-OCOCH3CH2CH2CH3CH2CH2CH35-acetoxy-N,N-dipropyltryptamine
5-AcO-MiPTartificial5-OCOCH3CH3CH(CH3)25-acetoxy-N-methyl-N-isopropyltryptamine
5-AcO-DiPTartificial5-OCOCH3CH(CH3)2CH(CH3)25-acetoxy-N,N-diisopropyltryptamine
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-DMTartificial5-OCH2C6H5CH3CH35-benzyloxy-N,N-dimethyltryptamine101832-88-6
5-HO-METartificial5-OHCH3CH2CH35-hydroxy-N-methyl-N-ethyltryptamine
5-HO-DETartificial5-OHCH2CH3CH2CH35-hydroxy-N,N-diethyltryptamine14009-42-8
5-HO-DPTartificial5-OHCH2CH2CH3CH2CH2CH35-hydroxy-N,N-dipropyltryptamine36288-75-2
5-HO-MiPTartificial5-OHCH3CH(CH3)25-hydroxy-N-methyl-N-isopropyltryptamine
5-HO-DiPTartificial5-OHCH(CH3)2CH(CH3)25-hydroxy-N,N-diisopropyltryptamine36288-76-3
5-Methyl-DMT (5,N,N-TMT) artificial 5-CH3 CH3 CH3 5,N,N-trimethyltryptamine 22120-39-4
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 [53] artificial 5-C(CH3)3 CH3 CH3 5-(tert-butyl)-N,N-dimethyltryptamine
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
artificial 5-F CH2CH3 CH2CH3 5-fluoro-N,N-diethyltryptamine
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
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
artificial 5-CF3 CH3 CH3 5-(trifluoromethyl)-N,N-dimethyltryptamine 2418713-32-1
5-TFMO-DMT[54] artificial 5-OCF3 CH3 CH3 5-(trifluoromethoxy)-N,N-dimethyltryptamine
5-Nitro-DMT[55] 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
Almotriptanartificial5-(CH2SO2N(CH2)4)CH3CH3N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1''H''-indol-3-yl]-ethanamine154323-57-6
Rizatriptanartificial5-(CH2(N3(CH)2))CH3CH3N,N-dimethyl-2-[5-(1''H''-1,2,4-triazol-1-ylmethyl)-1''H''-indol-3-yl]ethanamine145202-66-0
Sumatriptanartificial5-(CH2SO2NHCH3)CH3CH31-[3-(2-Dimethylaminoethyl)-1''H''-indol-5-yl]-N-methyl-methanesulfonamide103628-46-2
Zolmitriptanartificial5-(CHNHC=OOCH2)CH3CH35-(4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine139264-17-8
artificial 6-F CH3 CH3 6-fluoro-N,N-dimethyltryptamine 1511-31-5
6-Fluoro-DET[56] 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
artificial 6-CH3 CH3 CH3 6,N,N-trimethyltryptamine
artificial 6-OH CH3 CH3 6-hydroxy-N,N-dimethyltryptamine 1476-33-1
artificial 6-OH CH3 CH3 6-hydroxy-N,N-diethyltryptamine 1476-59-1
artificial 6-OCH3 CH3 CH3 6-methoxy-N,N-dimethyltryptamine 2426-88-2
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[57] artificial 7-Br CH3 CH3 7-bromo-N,N-dimethyltryptamine 74798-68-8
artificial 7-OH CH3 CH3 7-hydroxy-N,N-dimethyltryptamine 7578-26-9
artificial 7-OCH3 CH3 CH3 7-methoxy-N,N-dimethyltryptamine
7-Methoxy-MiPT artificial 7-OCH3 CH3 CH(CH3)27-methoxy-N-methyl-N-isopropyltryptamine
1-Methylpsilocinartificial1-CH3, 4-OHCH3CH31-Methyl-3-[2-(''N'',''N''-dimethylamino)ethyl]-4-hydroxyindole1465-16-3
1-Methyl-5-MeO-DiPTartificial1-CH3, 5-OCH3CH(CH3)2CH(CH3)21-methyl-5-methoxy-N,N-diisopropyltryptamine1373882-10-0
NBoc-DMT (NB-DMT)artificial1-OCOC(CH3)3CH3CH31-(t-butoxycarbonyl)-N,N-dimethyltryptamine
NB-5-MeO-MiPTartificial1-OCOC(CH3)3, 5-OCH3CH3CH(CH3)21-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
NB-5-MeO-DALTartificial1-OCOC(CH3)3, 5-OCH3H2C=CH-CH2H2C=CH-CH21-(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-TMTartificial2-CH3, 5-OCH3CH3CH32-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine67292-68-6
5-MeO-7-TMTartificial5-OCH3, 7-CH3CH3CH35-Methoxy-7,N,N-trimethyltryptamine61018-77-7
5-MeO-4-TMTartificial4-CH3, 5-OCH3 CH3CH35-Methoxy-4,N,N-trimethyltryptamine
4-HO-5-MeO-DMT (psilomethoxin)artificial4-OH, 5-OCH3CH3CH34-Hydroxy-5-methoxy-N,N-dimethyltryptamine2433-31-0
4-F-5-MeO-DMTartificial4-F, 5-OCH3CH3CH34-Fluoro-5-Methoxy-N,N-dimethyltryptamine312314-18-4
5-MeO-7-F-METartificial5-OCH3, 7-FCH3CH2CH35-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
EMDT (2-ethyl-5-MeO-DMT)artificial2-CH2CH3, 5-OCH3CH3CH32-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine263744-72-5
ST-1936 (2-methyl-5-chloro-DMT)artificial2-CH3, 5-ClCH3CH32-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine1210-81-7
Benanserin (benzyl antiserotonin; BAS; MC-4788; Sq-4788)artificial1-CH2C6H5, 2-CH3, 5-OCH3HH2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine441-91-8
O-4310 (1-isopropyl-6-fluoropsilocin)artificial1-CH(CH3)2, 4-OH, 6-FCH3CH33-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol885671-63-6
CP-132,484 (4,5-DHP-1-Me-T)artificial1-methyl-4,5-(OCH2CH2CH2)HH1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole143508-76-3
4,5-DHP-DMTartificial4,5-(OCH2CH2CH2)CH3CH31-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-''e'']indole135360-97-3
4,5-DHF-DMT (P-3)artificial[58] 4,5-(CH2CH2O)CH3CH32-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
4,5-Methylbenzoxazole-DMT (P-131)artificial4,5-(OC(CH3)=N)CH3CH3N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine
4,5-MDO-DMTartificial4,5-(OCH2O)CH3CH32-(2H,6H-[1,3]Dioxolo[4,5-''e'']indol-8-yl)-N,N-dimethylethan-1-amine81249-30-1
4,5-MDO-DiPTartificial4,5-(OCH2O)CH(CH3)2CH(CH3)2N-[2-(2''H'',6''H''-[1,3]Dioxolo[4,5-''e'']indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine82173-82-8
5,6-FUR-DMT (P-4)artificial5,6-(CH=CHO)CH3CH32-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine
5,6-MDO-DMTartificial5,6-(OCH2O)CH3CH32-(2H,5H-[1,3]Dioxolo[4,5-''f'']indol-7-yl)-N,N-dimethylethan-1-amine
5,6-MDO-MiPTartificial5,6-(OCH2O)CH3CH(CH3)2N-[2-(2''H'',5''H''-[1,3]Dioxolo[4,5-''f'']indol-7-yl)ethyl]-N-methylpropan-2-amine
5,6-MDO-DiPTartificial5,6-(OCH2O)CH(CH3)2CH(CH3)2N-[2-(2''H'',5''H''-[1,3]Dioxolo[4,5-''f'']indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine

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.[59] [60] [61] 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. This is analogous to α-methylation of phenethylamine into amphetamine.

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

StructureNameChemical nameCAS #
Tryptophan(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid73-22-3
5-Hydroxytryptophan (5-HTP)(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid4350-09-8
5-Methoxytryptophan (5-MTP)(2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid2504-22-5
α-Methyltryptophan(2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid16709-25-4
α-Methyl-5-HTP(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)-2-methylpropanoic acid150852-19-0
α-Methyl-5-MTP(2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)-2-methylpropanoic acid?
AMT (αMT; α-MT; Indopan)1-(1H-Indol-3-yl)propan-2-amine299-26-3
2,α-DMT (2-methyl-AMT)1-(2-methyl-1H-indol-3-yl)propan-2-amine4966-28-3
4-Methyl-AMT1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine3569-29-7
5-Fluoro-AMT1-(5-fluoro-1H-indol-3-yl)propan-2-amine712-08-3
5-Chloro-AMT1-(5-Chloro-1H-indol-3-yl)propan-2-amine712-07-2
5-HO-AMT (αMS/α-methyl-5-HT)3-(2-aminopropyl)-1H-indol-5-ol304-52-9
5-MeO-AMT1-(5-methoxy-1H-indol-3-yl)propan-2-amine1137-04-8
5-Ethoxy-AMT1-(5-ethoxy-1H-indol-3-yl)propan-2-amine101832-83-1
5-Isopropoxy-AMT1-propan-2-amine
5-Allyloxy-AMT1-propan-2-amine
1-Propyl-5-MeO-AMT1-(5-methoxy-1-propylindol-3-yl)propan-2-amine?
BW-723C861-[5-(2-Thienylmethoxy)-1''H''-indol-3-yl]-2-propanamine160521-72-2
6-Fluoro-AMT1-(6-fluoro-1H-indol-3-yl)propan-2-amine712-11-8
7-Chloro-AMT1-(7-chloro-1H-indol-3-yl)propan-2-amine711-99-9
AL-37350A (4,5-DHP-AMT)(S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-''e'']indole362603-40-5
Compound 5 [67] 1-(3H-benzo[e]indol-1-yl)propan-2-amine
AET (αET; α-ET)1-(1H-indol-3-yl)butan-2-amine2235-90-7
4-Methyl-AET1-(4-Methyl-1H-indol-3-yl)butan-2-amine28289-30-7
4-HO-AET1-(4-hydroxy-1H-indol-3-yl)butan-2-amine28289-28-3
5-Fluoro-AET1-(5-fluoro-1H-indol-3-yl)butan-2-amine1380137-98-3
5-Chloro-AET1-(5-chloro-1H-indol-3-yl)butan-2-amine?
5-Methyl-AET1-(5-methyl-1H-indol-3-yl)butan-2-amine1380148-21-9
5-MeO-AET1-(5-methoxy-1H-indol-3-yl)butan-2-amine4765-10-0
7-Methyl-AET1-(7-methyl-1H-indol-3-yl)butan-2-amine13712-80-6
α,N-DMT (SK&F-7024, Ro 3-1715; N-methyl-AMT)1-(1H-indol-3-yl)-N-methylpropan-2-amine299-24-1
N,N-Dimethyl-AMT (α,N,N-TMT)(2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine4761-32-4
N-Hydroxy-AMT (N-HO-AMT)N-[1-(1''H''-indol-3-yl)propan-2-yl]hydroxylamine63-33-2
N-Methyl-5-MeO-AMT (α,N,O-TMS/α,N,O-trimethyl-5-HT)[1-(5-methoxy-1''H''-indol-3-yl)propan-2-yl](methyl)amine4822-13-3
N,N-Dimethyl-5-MeO-AMT (5-MeO-α,N,N-TMT)(2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine101831-90-7
α-Propyltryptamine (APT; αPT; α-PT)1-(1H-indol-3-yl)pentan-2-amine
Indolylpropylaminopentane (IPAP; α,N-DPT)1-(1H-indol-3-yl)-N-propylpentan-2-amine
α-Methyl-DiPT(2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
MPMI[68] 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143321-54-4
Lucigenol (4-HO-MPMI)3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole?
5-MeO-MPMI (CP-108509)5-Methoxy-3--1H-indole143321-57-7
5-Fluoro-MPMI[69] 5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole?
5-Bromo-MPMI5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143322-57-0
Eletriptan3--5-[2-(benzenesulfonyl)ethyl]-1H-indole143322-58-1
Z5247692566[70] 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine
BK-NM-AMT (α,N-dimethyl-β-ketotryptamine)[71] [72] [73] 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine)[74] [75] [76] 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[77] [78] 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine)[79] [80] 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one

List of substituted β-ketotryptamines

A number of β-ketotryptamines (beta-ketotryptamines) are known. 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. They act as monoamine releasing agents.

Cyclized tryptamines

Examples of cyclized tryptamines include:

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

Related compounds

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

StructureNameChemical nameCAS #
C-DMT (1-carba-DMT)2-(3H-inden-1-yl)-N,N-dimethylethanamine
O-DMT (1-oxa-DMT, DMBF)2-(1-benzofuran-3-yl)-N,N-dimethylethanamine
MiPBF (1-oxa-MiPT)N-[2-(1-benzofuran-3-yl)ethyl]-N-methylpropan-2-amine
Dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT)2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine140853-58-3
5-MeO-DiBF (1-oxa-5-MeO-DiPT)N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
3-APB (1-oxa-AMT)3-(2-aminopropyl)benzofuran105909-13-5
Mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT)3-(2-aminopropyl)-5-methoxybenzofuran140853-59-4
S-DMT (1-thia-DMT)2-(1-benzothiophen-3-yl)-N,N-dimethylethanamine10275-64-6
3-APBT (SKF-6678; 1-thia-AMT)1-(1-benzothiophen-3-yl)propan-2-amine1201-27-0
Isotryptamine (isoT)2-indol-1-ylethanamine13708-58-2
isoAMT1-indol-1-ylpropan-2-amine1227465-67-9
(S)-5,6-Difluoro-isoAMT [81] (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-amine169675-09-6
isoDMT2-indol-1-yl-N,N-dimethylethanamine87482-09-5
5-MeO-isoDMT2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine244122-80-3
6-MeO-isoDMT2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine87482-11-9
Zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-Me-isoDMT)(2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine2481740-94-5
2ZEDMA2-indolizin-1-yl-N,N-dimethylethanamine
1ZP2MA1-indolizin-1-yl-N-methylpropan-2-amine
1Z2MAP1O1-indolizin-3-yl-2-(methylamino)propan-1-one2110204-31-2
Example 16 [82] [83] 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
Example 1 [84] 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-amine259857-99-3
AL-34662 (indazole-5-HO-AMT)1-((S)-2-Aminopropyl)-1H-indazol-6-ol210580-75-9
O-Methyl-AL-34662 (indazole-5-MeO-AMT)1-((S)-6-methoxy-2-aminopropyl)-1H-indazole210580-60-2
7-Methyl-AL-346621-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol874668-67-4
7-Chloro-AL-346621-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol874881-86-4
AL-38022A(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine478132-11-5
Example 9 [85] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine478132-12-6
Example 3 [86] (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine890087-75-9
Example 1 [87] (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-amine372163-84-3
2-Desethyl-YM-348 [88] (2S)-1-(1H-furo[2,3-''g'']indazol-1-yl)propan-2-amine748116-94-1
I-32 [89] 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
2-Azapsilocin (Psilocin indazole analogue, P-6)[90] 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-indole2945139-94-4
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[91] 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole3027515-24-5
(R)-693-[(5''R'')-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine2765652-48-8
(R)-703-[(3''R'')-1,3-dimethyl-3,6-dihydro-2''H''-pyridin-5-yl]-1H-pyrrolo[2,3-b]pyridine?
SN-223-(1-methylpiperidin-4-yl)-1H-indole17403-07-5
RU-24,9695-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole107008-28-6
EMD-3860885-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole54635-62-0
T-70[92] N,N-dimethyl-2-(6H-thieno[2,3-''b'']pyrrol-4-yl)ethan-1-amine?
T-72[93] N,N-dimethyl-2-(4H-thieno[3,2-''b'']pyrrol-6-yl)ethan-1-amine?
Gramine1-(1H-indol-3-yl)-N,N-dimethylmethanamine87-52-5
Homotryptamine3-(1H-indol-3-yl)propan-1-amine6245-89-2
Dimethylhomotryptamine (DMHT)3-(1H-indol-3-yl)-N,N-dimethylpropan-1-amine13117-35-6
Indalpine3-(2-piperidin-4-ylethyl)-1H-indole63758-79-2

External links

Notes and References

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  4. Book: Shulgin AT . Chemistry of Psychotomimetics . 3–29 . Hoffmeister F, Stille G . Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs . Handbook of Experimental Pharmacology . Springer Berlin Heidelberg . Berlin . 1982 . 55 / 3 . 978-3-642-67772-4 . 8130916 . 10.1007/978-3-642-67770-0_1 . https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1.
  5. Book: Alexander T. Shulgin . Hallucinogens . 1109–1137 . https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 . Burger A, Wolf ME . Burger's Medicinal Chemistry . 4 . 3 . 1980 . Wiley . New York . 978-0-471-01572-7 . 219960627 .
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  11. Nen . Entheogenic effects of NMT from Acacia . Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011 . 4 December 2011 . https://web.archive.org/web/20120226052047/http://www.entheo.net/files/webfiles/ega11_program_v7.pdf . 15 April 2025 . 5 April 2025 . https://archive.today/20250405014754/https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=300323&%23post300323 . bot: unknown .
  12. Nen . NMT: A Spatial Hallucinogen With Therapeutic Applications . Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013 . 13 July 2013 . https://breakingconvention.co.uk/archive#conferenceArchive.
  13. Book: Liechti ME, Holze F . Disruptive Psychopharmacology . Dosing Psychedelics and MDMA . Curr Top Behav Neurosci . 56 . 3–21 . 2022 . 34734392 . 10.1007/7854_2021_270 . 978-3-031-12183-8 .
  14. Holze F, Singh N, Liechti ME, D'Souza DC . Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile . Biol Psychiatry Cogn Neurosci Neuroimaging . 9 . 5 . 472–489 . May 2024 . 38301886 . 10.1016/j.bpsc.2024.01.007 . free .
  15. Dos Santos RG, Hallak JE . Ayahuasca: pharmacology, safety, and therapeutic effects . CNS Spectr . 30 . 1 . e2 . November 2024 . 39564645 . 10.1017/S109285292400213X . DMT has been found to be inactive orally in doses as high as 1 g, but it has been found to be psychoactive after intramuscular administration (0.25-2.00 mg/kg), when inhaled as vaporized free-base (0.2-0.7 mg/kg), and after intravenous administration (0.2-0.4 mg/kg).8–10 [...] In the case of ayahuasca, since pure DMT is not orally psychoactive (doses up to 1 g are inactive in humans51) due to peripheral (gastrointestinal and hepatic) metabolization by MAO-A, [...]. free .
  16. Barker SA . Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT . Psychopharmacology (Berl) . 239 . 6 . 1749–1763 . June 2022 . 35064294 . 8782705 . 10.1007/s00213-022-06065-0 . 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)..
  17. Egger K, Aicher HD, Cumming P, Scheidegger M . Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors . Cell Mol Life Sci . 81 . 1 . 395 . September 2024 . 39254764 . 11387584 . 10.1007/s00018-024-05353-6 . 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]..
  18. Ott J . Pharmahuasca: human pharmacology of oral DMT plus harmine . J Psychoactive Drugs . 31 . 2 . 171–177 . 1999 . 10438001 . 10.1080/02791072.1999.10471741 . 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 [...].
  19. Book: Brimblecombe RW, Pinder RM . Indolealkylamines and Related Compounds . 98–144 . Hallucinogenic Agents . 1975 . Wright-Scientechnica . Bristol . 978-0-85608-011-1 . 2176880 . OL4850660M . 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..
  20. Book: Nichols DE, Glennon RA . Jacobs BL . Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens . Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives . New York . 95–142 . 1984 . Raven Press . 978-0-89004-990-7 . 10324237 . https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95 . 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). .
  21. Szára . S. . 104 Correlation between Metabolism and Behavioural Action of Psychotropic Tryptamine Derivatives . Biochemical Pharmacology . 8 . 1 . 1961 . 10.1016/0006-2952(61)90278-7 . 32 . N,N-dimethyltryptamine and its N,N-diethyl and N,N-dipropyl homologues produce autonomic symptoms, perceptual, emotional, and thinking disturbances in man (in doses of 1 mg/kg) similar to LSD25 or mescalin but for a much shorter period of time. The corresponding dibutyl derivative causes only very slight symptoms while the dihexyl compound is completely inactive in the same dose..
  22. Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA . Toxicology and Analysis of Psychoactive Tryptamines . International Journal of Molecular Sciences . 21 . 23 . 9279 . December 2020 . 33291798 . 7730282 . 10.3390/ijms21239279 . 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]. . free .
  23. Ludbrook G, Bryson N, Taylor B, Hocevar-Trnka J, Johnson MW, Hirman J, Morrish G, Alexander R, Pollack M . Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study . J Clin Psychopharmacol . 45 . 5 . 441–453 . 2025 . 40685873 . 12379775 . 10.1097/JCP.0000000000002047 .
  24. Web site: 4-AcO-DMT (Ацетилпсилоцин) . АИПСИН . ru . 1 January 2026.
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  26. Book: . Shamanic-Snuff Psychonautica: Pharmañopo: Bufotenine—Psychonautics . 99–116 (105–112, 114–115) . Shamanic Snuffs or Entheogenic Errhines . Entheobotanica . 2001 . 978-1-888755-02-2 . 56061312 . https://archive.org/details/vdocuments.mx_unknown-55b347d139b58/page/n51/mode/1up . 24 January 2025 .
  27. Web site: A New One-Hour Talk On 5-MeO-DMT . . Patreon . . 1 December 2022 . 21 January 2025 . 6:27–8:40, 10:15–11:13 . [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. .
  28. PODCAST 28: A talk with Jonathan Ott . . Patreon . . 1 September 2021 . 49:20–50:36 . 20 January 2025 . [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. .
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  31. POD 126: The Return of Psychedelic Selenium with Dr. Josh Hartsel . . Patreon . . 29 April 2025 . 1:33:53–1:35:50 . [...] [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 of N-methyl-AMT, which is active, or AMT itself maybe. [...].
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