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general/tryptamines

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Substituted tryptamine

Class of indoles

Substituted tryptamine

Class of indoles

The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN<sub>1</sub>=RN<sub>2</sub>=Rα = H.
The structure of substituted tryptamines with all positions labeled.

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

CompoundChemical nameDoseDuration
Tryptamine (T)Tryptamine100 mga–
NMT*N*-MethyltryptamineUnknownb–
NET*N*-EthyltryptamineUnknownUnknown
NiPT*N*-IsopropyltryptamineUnknownUnknown
NsBT*N*-*sec*-Butyltryptamine25–75 mg"Short"
NtBT*N*-*tert*-Butyltryptamine5–20 mgUnknown
NAT*N*-Amyltryptamine100 mg–
NHT*N*-Hexyltryptamine100 mg–
DMT*N*,*N*-Dimethyltryptamine350–1,000 mgc–
DET*N*,*N*-Diethyltryptamine50–150 mg2–4 hours
DPT*N*,*N*-Dipropyltryptamine100–250 mg2–4 hours
DiPT*N*,*N*-Diisopropyltryptamine25–100 mg (15–150 mg+)4–8 hours
DALT*N*,*N*-Diallyltryptamine60–80 mg
DBT*N*,*N*-Dibutyltryptamine≥100 mgUnknown
DAT*N*,*N*-DiamyltryptamineUnknownUnknown
DHT*N*,*N*-Dihexyltryptamine100 mg–
MET*N*-Methyl-*N*-ethyltryptamine80–100 mgUnknown
MPT*N*-Methyl-*N*-propyltryptamine50 mgUnknown
MiPT*N*-Methyl-*N*-isopropyltryptamine10–25 mg3–4 hours
MALT*N*-Methyl-*N*-allyltryptamine25–50 mgUnknown
MBT*N*-Methyl-*N*-butyltryptamine250–400 mg4–6 hours
MsBT*N*-Methyl-*N*-*sec*-butyltryptamine250–400 mgUnknown
EPT*N*-Ethyl-*N*-propyltryptamineUnknownUnknown
EiPT*N*-Ethyl-*N*-isopropyltryptamine24–40 mg4–6 hours
PiPT*N*-Propyl-*N*-isopropyltryptamineUnknownUnknown
Pyr-T*N*,*N*-TetramethylenetryptamineUnknownUnknown
Pip-T*N*,*N*-PentamethylenetryptamineUnknownUnknown
Mor-T3-(2-Morpholinoethyl)indoleUnknowndUnknown
**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 d = Mor-T was inactive at a dose of 30mg by intramuscular injection. **Refs:** *Individual:*

4-Hydroxytryptamines

CompoundChemical nameDoseDuration
[4-HT](4-hydroxytryptamine) (4-HO-T)4-HydroxytryptamineUnknownUnknown
Norbaeocystin (4-PO-T)4-PhosphoryloxytryptamineUnknownUnknown
Norpsilocin (4-HO-NMT)4-Hydroxy-*N*-methyltryptamineUnknownUnknown
Baeocystin (4-PO-NMT)4-Phosphoryloxy-*N*-methyltryptamine4–10 mgaUnknown
Psilocin (4-HO-DMT)4-Hydroxy-*N*,*N*-dimethyltryptamine10–20 mg (5–40 mg+)3–6 hours
Psilocybin (4-PO-DMT)4-Phosphoryloxy-*N*,*N*-dimethyltryptamine10–20 mg (5–40 mg+)3–6 hours
[4-AcO-DMT](4-aco-dmt) (psilacetin)4-Acetoxy-*N*,*N*-dimethyltryptamine10–30 mg3–8 hours
[4-PrO-DMT](4-pro-dmt)4-Propionyloxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[4-HO-DET](4-ho-det) (ethocin)4-Hydroxy-*N*,*N*-diethyltryptamine10–25 mg4–6 hours
Ethocybin (4-PO-DET)4-Phosphoryloxy-*N*,*N*-diethyltryptamine15–30 mg4–6 hours
[4-HO-DPT](4-ho-dpt) (deprocin)4-Hydroxy-*N*,*N*-dipropyltryptamine20 mg5–8 hours
[4-HO-DiPT](4-ho-dipt) (iprocin)4-Hydroxy-*N*,*N*-diisopropyltryptamine12–20 mg (3–30 mg+)2–3 hours
[4-AcO-DiPT](4-aco-dipt) (ipracetin)4-Acetoxy-*N*,*N*-diisopropyltryptamine6–10 mgUnknown
Luvesilocin (4-GO-DiPT)4-Glutaryloxy-*N*,*N*-diisopropyltryptamineUnknownbUnknownb
[4-HO-DALT](4-ho-dalt) (daltocin)4-Hydroxy-*N*,*N*-diallyltryptamineUnknownUnknown
[4-HO-DBT](4-ho-dbt)4-Hydroxy-*N*,*N*-dibutyltryptamine20 mgUnknown
[4-HO-DiBT](4-ho-dibt)4-Hydroxy-*N*,*N*-diisobutyltryptamine20 mgUnknown
[4-HO-DtBT](4-ho-dtbt)4-Hydroxy*N*,*N*-di-*tert*-butyltryptamineUnknownUnknown
[4-HO-MET](4-ho-met) (metocin)4-Hydroxy-*N*-methyl-*N*-ethyltryptamine10–20 mg (2–45 mg+)4–6 hours
[4-HO-MPT](4-ho-mpt) (meprocin)4-Hydroxy-*N*-methyl-*N*-propyltryptamine8–30 mgUnknown
[4-HO-MiPT](4-ho-mipt) (miprocin)4-Hydroxy-*N*-methyl-*N*-isopropyltryptamine12–25 mg (6–30 mg)4–6 hours
[4-HO-MALT](4-ho-malt) (maltocin)4-Hydorxy-*N*-methyl-*N*-allyltryptamineUnknownUnknown
[4-HO-MtBT](4-ho-mtbt)4-Hydroxy-*N*-methyl-*N*-*tert*-butyltryptamine15 mgUnknown
[4-HO-EPT](4-ho-ept) (eprocin)4-Hydroxy-*N*-ethyl-*N*-propyltryptamineUnknownUnknown
[4-HO-EiPT](4-ho-eipt)4-Hydroxy-*N*-ethyl-*N*-isopropyltryptamineUnknownUnknown
[4-HO-PiPT](4-ho-pipt) (piprocin)4-Hydroxy-*N*-propyl-*N*-isopropyltryptamineUnknownUnknown
[4-HO-TMT](4-ho-tmt)4-Hydroxy-*N*,*N*,*N*-trimethyltryptamineUnknownUnknown
Aeruginascin (4-PO-TMT)4-Phosphoryloxy-*N*,*N*,*N*-trimethyltryptamineUnknownUnknown
[4-HO-pyr-T](4-ho-pyr-t)4-Hydroxy-*N*,*N*-tetramethylenetryptamine20 mgUnknown
**Footnotes:** a = Baeocystin has conflicting reports, some say that it's active and some say that it's inactive. b = Luvesilocin is known to be active subcutaneously at doses of 5 to 40mg with an average duration of 3.6hours. **Refs:** *Individual:*

5-Hydroxytryptamines

CompoundChemical nameDoseDuration
Serotonin (5-HT, 5-HO-T)5-Hydroxytryptamine100 mga–
*N*-Methylserotonin (norbufotenin; 5-HO-NMT)5-Hydroxy-*N*-methyltryptamineUnknownUnknown
Bufotenin (5-HO-DMT)5-Hydroxy-*N*,*N*-dimethyltryptamine100 mgb–
*O*-Acetylbufotenin (5-AcO-DMT)5-Acetoxy-*N*,*N*-dimethyltryptamineUnknownUnknown
*O*-Pivalylbufotenin (5-*t*-BuCO-DMT)5-Pivaloxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[5-HO-DET](5-ho-det)5-Hydroxy-*N*,*N*-diethyltryptamineUnknownUnknown
[5-HO-DPT](5-ho-dpt) (DiPS, NDPS)5-Hydroxy-*N*,*N*-dipropyltryptamineUnknownUnknown
[5-HO-DiPT](5-ho-dipt)5-Hydroxy-*N*,*N*-diisopropyltryptamineUnknownUnknown
[5-HO-MET](5-ho-met)5-Hydroxy-*N*-methyl-*N*-ethyltryptamineUnknownUnknown
**Footnotes:** a = Serotonin does not cross the blood–brain barrier and is not psychoactive. b = Bufotenin is not orally active, but is active intravenously at doses of 8 to 16mg with a duration of 1 to 2hours and is active via insufflation and other parenteral routes. **Refs:** *Individual:*

5-Methoxytryptamines

CompoundChemical nameDoseDuration
[5-MT](5-methoxytryptamine) (5-MeO-T)5-MethoxytryptamineUnknownUnknown
[5-MeO-NMT](5-meo-nmt)5-Methoxy-*N*-methyltryptamineUnknownUnknown
[5-MeO-NET](5-meo-net)5-Methoxy-*N*-ethyltryptamineUnknownUnknown
[5-MeO-NiPT](5-meo-nipt)5-Methoxy-*N*-isopropyltryptamineUnknownUnknown
[5-MeO-DMT](5-meo-dmt) (mebufotenin)5-Methoxy-*N*,*N*-dimethyltryptamine35 mga–
[5-MeO-DET](5-meo-det)5-Methoxy-*N*,*N*-diethyltryptamine1–3 mg3–4 hours
[5-MeO-DPT](5-meo-dpt)5-Methoxy-*N*,*N*-dipropyltryptamine6–10 mg2–4 hours
[5-MeO-DiPT](5-meo-dipt)5-Methoxy-*N*,*N*-diisopropyltryptamine6–12 mg4–8 hours
[5-MeO-DALT](5-meo-dalt)5-Methoxy-*N*,*N*-diallyltryptamine12–25 mg2–4 hours
[5-MeO-DBT](5-meo-dbt)5-Methoxy-*N*,*N*-dibutyltryptamineUnknownUnknown
[5-MeO-DsBT](5-meo-dsbt)5-Methoxy-*N*,*N*-di-*sec*-butyltryptamineUnknownUnknown
[5-MeO-MET](5-meo-met)5-Methoxy-*N*-methyl-*N*-ethyltryptamineUnknownUnknown
[5-MeO-MPT](5-meo-mpt)5-Methoxy-*N*-methyl-*N*-propyltryptamineUnknownUnknown
[5-MeO-MiPT](5-meo-mipt)5-Methoxy-*N*-methyl-*N*-isopropyltryptamine4–6 mg (0.5–20 mg+)4–6 hours
[5-MeO-MALT](5-meo-malt)5-Methoxy-*N*-methyl-*N*-allyltryptamineUnknownUnknown
[5-MeO-MsBT](5-meo-msbt)5-Methoxy-*N*-methyl-*N*-*sec*-butyltryptamine10–30 mg3–4 hours
[5-MeO-EPT](5-meo-ept)5-Methoxy-*N*-ethyl-*N*-propyltryptamineUnknownUnknown
[5-MeO-EiPT](5-meo-eipt)5-Methoxy-*N*-ethyl-*N*-isopropyltryptamineUnknownUnknown
[5-MeO-PiPT](5-meo-pipt)5-Methoxy-*N*-propyl-*N*-isopropyltryptamineUnknownUnknown
[5-MeO-iPALT](5-meo-ipalt) (ASR-3001)5-Methoxy-*N*-isopropyl-*N*-allyltryptamine8–14 mg1.5–2.5 hours
[5-MeO-pyr-T](5-meo-pyr-t)5-Methoxy-*N*,*N*-tetramethylenetryptamine0.5–2 mgSeveral hours
Melatonin (5-MeO-NAcT)5-Methoxy-*N*-acetyltryptamine1–10 mgbA few hours
**Footnotes:** a = [5-MeO-DMT](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

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

Other tryptamines

CompoundChemical nameDoseDuration
Lespedamine (1-MeO-DMT)1-Methoxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[2-Methyl-DMT](2-methyl-dmt)2-Methyl-*N*,*N*-dimethyltryptamine50–100 mg4–6 hours
[2-Methyl-DET](2-methyl-det)2-Methyl-*N*,*N*-diethyltryptamine80–120 mg6–8 hours
[4-MeO-DMT](4-meo-dmt)4-Methoxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[4-MeO-DET](4-meo-det)4-Methoxy-*N*,*N*-diethyltryptamine30 mgUnknown
[4-MeO-DiPT](4-meo-dipt)4-Methoxy-*N*,*N*-diisopropyltryptamineUnknownUnknown
[4-MeO-MiPT](4-meo-mipt)4-Methoxy-*N*-methyl-*N*-isopropyltryptamines20–30 mg4–6 hours
[4,5-MDO-DMT](4-5-mdo-dmt)4,5-Methylenedioxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[4,5-MDO-DiPT](4-5-mdo-dipt)4,5-Methylenedioxy-*N*,*N*-diisopropyltryptamine25 mgUnknown
[5-Fluoro-DMT](5-fluoro-dmt)5-Fluoro-*N*,*N*-dimethyltryptamineUnknownUnknown
[5-Chloro-DMT](5-chloro-dmt)5-Chloro-*N*,*N*-dimethyltryptamineUnknownUnknown
[5-Bromo-DMT](5-bromo-dmt)5-Bromo-*N*,*N*-dimethyltryptamineUnknownaUnknown
Bretisilocin (5-fluoro-MET)5-Fluoro-*N*-methyl-*N*-ethyltryptamineUnknownbUnknownb
[5-MeO-2-TMT](5-meo-tmt)5-Methoxy-2-methyl-*N*,*N*-dimethyltryptamine75–150 mg5–10 hours
[5-MeS-DMT](5-mes-dmt)5-Methylthio-*N*,*N*-dimethyltryptamineUnknowncUnknownc
[5,6-MeO-MiPT](5-6-meo-mipt)5,6-Dimethoxy-*N*-methyl-*N*-isopropyltryptamine75 mgUnknown
[5,6-MDO-DMT](5-6-mdo-dmt)5,6-Methylenedioxy-*N*,*N*-dimethyltryptamine5 mgUnknown
[5,6-MDO-DiPT](5-6-mdo-dipt)5,6-Methylenedioxy-*N*,*N*-diisopropyltryptamineUnknownUnknown
[5,6-MDO-MiPT](5-6-mdo-mipt)5,6-Methylenedioxy-*N*-methyl-*N*-isopropyltryptamine50–60 mgUnknown
[6-Fluoro-DMT](6-fluoro-dmt)6-Fluoro-*N*,*N*-dimethyltryptamineUnknownUnknown
[6-Fluoro-DET](6-fluoro-det)6-Fluoro-*N*,*N*-diethyltryptamine80 mgUnknown
[6-HO-DMT](6-ho-dmt)6-Hydroxy-*N*,*N*-dimethyltryptamine80 mgUnknown
[6-HO-DET](6-ho-det)6-Hydroxy-*N*,*N*-diethyltryptamine≥10 mgd3–4 hoursd
[6-MeO-DMT](6-meo-dmt)6-Methoxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[6-MeO-DiPT](6-meo-dipt)6-Methoxy-*N*,*N*-diisopropyltryptamine50 mgUnknown
[6-MeO-MiPT](6-meo-mipt)6-Methoxy-*N*-methyl-*N*-isopropyltryptamine50 mgUnknown
[7-HO-DMT](7-ho-dmt)7-Hydroxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[7-MeO-DMT](7-meo-dmt)7-Methoxy-*N*,*N*-dimethyltryptamineUnknownUnknown
[7-MeO-DiPT](7-meo-dipt)7-Methoxy-*N*,*N*-diisopropyltryptamine70 mgUnknown
[7-MeO-MiPT](7-meo-mipt)7-Methoxy-*N*-methyl-*N*-isopropyltryptamine70 mgUnknown
**Footnotes:** a = [5-Bromo-DMT](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](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 d = Controversial and uncertain. **Refs:** *Individual:*

Interactions

Pharmacology

Pharmacodynamics

Compound[5-HT1A](5-ht1a)[5-HT1B](5-ht1b)[5-HT1D](5-ht1d)[5-HT1E](5-ht1e)[5-HT2A](5-ht2a)[5-HT2B](5-ht2b)[5-HT2C](5-ht2c)[5-HT3](5-ht3)[5-HT5A](5-ht5a)[5-HT6](5-ht6)[5-HT7](5-ht7)SERT
DMT269447117380380112257–2,090275692,400
Psilocin3721919833920025245–44779872,570
Psilocybin5,250–195–8514793,090––776––
[4-AcO-MALT](4-aco-malt)977–87141769225631––6617943,090
Bufotenin8.35922252246.2209166302188.91,120
[5-MeO-DMT](5-meo-dmt)10912157520015490–589254.4–
[5-MeO-DiPT](5-meo-dipt)170–871–32446–––2,190––
[5-MeO-DALT](5-meo-dalt)171,020549774571002,240––162604,470
[5-MeO-EiPT](5-meo-eipt)541,170174–1,62298–––4076615,620
LSD5.9213.51358.55.517–1.8168.5–
Compound[5-HT1A](5-ht1a)[5-HT1B](5-ht1b)[5-HT1D](5-ht1d)[5-HT1E](5-ht1e)[5-HT2A](5-ht2a)[5-HT2B](5-ht2b)[5-HT2C](5-ht2c)[5-HT3](5-ht3)[5-HT5A](5-ht5a)[5-HT6](5-ht6)[5-HT7](5-ht7)SERT
DMT10,00010,000934562,32310833510,0006114878833,742
DPT328546192,3382,579421,56710,0004,3734,543284157
DiPT12110,0003,74210,00010,00039910,00010,00010,00010,0003,4231,258
Psilocin6330519443404.714110,000707272852
[5-MeO-DMT](5-meo-dmt)1.9746.33602,0113,88453810,000277363.92,032
[5-MeO-DiPT](5-meo-dipt)1325,1371,71810,00010,00016310,00010,00010,00010,0001,2312,531
[5-MeO-MiPT](5-meo-mipt)12303233,496448592,18610,000953130206,409
[6-Fluoro-DMT](6-fluoro-dmt)393218554618663067410,0009612641145
[5-MeO-2-TMT](5-meo-2-tmt)20010,0002501,80010,000?4,020?10,4506014510,000
EMDT17010,00029052010,000?1,810?4,6201630010,000
Ibogaine10,00010,00010,000?14,142?10,00010,000???549
LSD7.33.97.89311303110,00096.96.610,000

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. Other tryptamine synthesis routes have also been described, for instance starting with tryptamine rather than indole.

List of substituted tryptamines

StructureNameOriginRing sub.RN1RN2Chemical nameCAS #
[[File:Tryptamine structure.svg130pxclass=skin-invert-image]]Tryptamine (T)Animals, plants, fungiHHH3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine61-54-1
[[File:NMT structure.svg120pxclass=skin-invert-image]]NMTPlantsHHCH3*N*-methyltryptamine61-49-4
[[File:2-Hydroxy-NMT.svg120pxclass=skin-invert-image]][2-HO-NMT](2-ho-nmt)Plants2-OHHCH32-hydroxy-*N*-methyltryptamine106987-89-7
[[File:5-MeO-NMT.svg120pxclass=skin-invert-image]][5-MeO-NMT](5-meo-nmt)Plants5-OCH3HCH35-methoxy-*N*-methyltryptamine2009-03-2
[[File:Serotonin-2D-skeletal.svg120pxclass=skin-invert-image]]Serotonin (5-HT)Animals, plants5-OHHH5-hydroxytryptamine50-67-9
[[File:Norbufotenine.svg120pxclass=skin-invert-image]]*N*-Methylserotonin (NMS; norbufotenin; 5-HO-NMT)Plants5-OHHCH35-hydroxy-*N*-methyltryptamine1134-01-6
[[File:Bufotenin2DACS.svg120pxclass=skin-invert-image]]Bufotenin (5-HO-DMT)Animals, plants, fungi5-OHCH3CH35-hydroxy-*N*,*N*-dimethyltryptamine487-93-4
[[File:Bufotenidine.png120pxclass=skin-invert-image]]Bufotenidine (5-HTQ)Amphibians5-O−(CH3)33-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate487-91-2
[[File:Bufoviridine.svg120pxclass=skin-invert-image]]Bufoviridine (5-SO-DMT)Amphibians5-SOCH3CH35-sulfooxy-*N*,*N*-dimethyltryptamine16369-08-7
[[File:Melatonin.svg120pxclass=skin-invert-image]]Melatonin (5-MeO-NAcT)Animals, plants, microbes5-OCH3HO=C-CH35-methoxy-*N*-acetyltryptamine73-31-4
[[File:N-acetylserotonin.svg120pxclass=skin-invert-image]]*N*-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT)Animals5-OHHO=C-CH35-hydroxy-*N*-acetyltryptamine1210-83-9
[[File:6-Hydroxymelatonin structure.svg120pxclass=skin-invert-image]][6-Hydroxymelatonin](6-hydroxymelatonin)Animals5-OCH3, 6-OHHO=C-CH3*N*-[2-(6-Hydroxy-5-methoxy-1*H*-indol-3-yl)ethyl]acetamide2208-41-5
[[File:4-Hydroxytryptamine.svg120pxclass=skin-invert-image]][4-Hydroxytryptamine](4-hydroxytryptamine) (4-HT)Fungi4-OHHH4-hydroxytryptamine570-14-9
[[File:Norpsilocin.svg120pxclass=skin-invert-image]][4-HO-NMT](4-ho-nmt)Fungi4-OHHCH34-hydroxy-*N*-methyltryptamine28363-70-4
[[File:Psilocin.svg120pxclass=skin-invert-image]]Psilocin (4-HO-DMT)Fungi4-OHCH3CH34-hydroxy-*N*,*N*-dimethyltryptamine520-53-6
[[File:4-HO-TMT.svg120pxclass=skin-invert-image]][4-HO-TMT](4-ho-tmt)Fungi4-OHCH3CH34-hydroxy-*N*,*N*,*N*-trimethyltryptammonium262285-41-6
[[File:Norbaeocystin.svg120pxclass=skin-invert-image]]Norbaeocystin (4-PO-T)Fungi4-OPO3H2HH4-phosphoryloxy-tryptamine21420-59-7
[[File:Baeocystin v2.svg120pxclass=skin-invert-image]]Baeocystin (4-PO-NMT)Fungi4-OPO3H2HCH34-phosphoryloxy-*N*-methyl-tryptamine21420-58-6
[[File:Psilocybin, Kekulé, skeletal formula of canonical psilocybin.svg120pxclass=skin-invert-image]]Psilocybin (4-PO-DMT)Fungi4-OPO3H2CH3CH34-phosphoryloxy-*N*,*N*-dimethyltryptamine520-52-5
[[File:Aeruginascin.png120pxclass=skin-invert-image]]Aeruginascin (4-PO-TMT)Fungi4-OPO3H2(CH3)3[3-[2-(trimethylazaniumyl)ethyl]-1*H*-indol-4-yl] hydrogen phosphate114264-95-8
[[File:DMT.svg120pxclass=skin-invert-image]]DMTAnimals, plantsHCH3CH3*N*,*N*-dimethyltryptamine61-50-7
[[File:Lespedamine.svg120pxclass=skin-invert-image]]Lespedamine (1-MeO-DMT)Plants1-OCH3CH3CH31-methoxy-*N*,*N*-dimethyltryptamine4335-93-7
[[File:5-MeO-DMT.svg120pxclass=skin-invert-image]][5-MeO-DMT](5-meo-dmt) (mebufotenin)Animals, plants5-OCH3CH3CH35-methoxy-*N*,*N*-dimethyltryptamine1019-45-0
[[File:5-Bromo-DMT.svg120pxclass=skin-invert-image]][5-Bromo-DMT](5-bromo-dmt)Marine sponges, invertebrates5-BrCH3CH35-bromo-*N*,*N*-dimethyltryptamine17274-65-6
[[File:6-Br-T.svg120pxclass=skin-invert-image]][6-Bromotryptamine](6-bromotryptamine)Marine invertebrates6-BrHH6-bromotryptamine96624-18-9
[[File:5,6_diBr-T.svg120pxclass=skin-invert-image]][5,6-Dibromotryptamine](5-6-dibromotryptamine)Marine invertebrates5,6-BrHH5,6-dibromotryptamine
[[File:5,6_diBr-NMT.svg120pxclass=skin-invert-image]][5,6-Dibromo-NMT](5-6-dibromo-nmt)Marine invertebrates5,6-BrHCH35,6-dibromo-*N*-methyltryptamine
[[File:5,6-dibromo-DMT.svg120pxclass=skin-invert-image]][5,6-Dibromo-DMT](5-6-dibromo-dmt)Marine sponges, invertebrates5,6-BrCH3CH35,6-dibromo-*N*,*N*-dimethyltryptamine72853-80-6
[[File:Desformylflustrabromine.svg120pxclass=skin-invert-image]]Desformylflustrabromine (dFBr)Marine invertebrates2-(α,α-dimethylallyl), 6-BrHCH32-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine474657-72-2
[[File:Convolutindole A.svg120pxclass=skin-invert-image]]Convolutindole AMarine invertebrates2,4,6-Br, 1,7-OCH3CH3CH31,7-dimethoxy-2,4,6-tribromo-*N*,*N*-dimethyltryptamine443356-86-3
[[File:Acetryptine.svg120pxclass=skin-invert-image]]Acetryptine (5-AT)artificial5-COCH3HH5-Acetyltryptamine3551-18-6
[[File:5-Phenoxytryptamine.svg130pxclass=skin-invert-image]][5-PhO-T](5-phenoxytryptamine)artificial5-OC6H5HH5-Phenoxytryptamine31363-70-9
[[File:5-Benzyloxytryptamine chemical structure.svg130pxclass=skin-invert-image]][5-BT](5-benzyloxytryptamine)artificial5-OCH2C6H5HH5-Benzyloxytryptamine20776-45-8
[[File:5-Carboxamidotryptamine.svg120pxclass=skin-invert-image]][5-CT](5-carboxamidotryptamine)artificial5-CONH2HH5-Carboxamidotryptamine74885-09-9
[[File:5-Nonyloxytryptamine.svg130pxclass=skin-invert-image]][5-NOT](5-nonyloxy-tryptamine)artificial5-O(CH2)8CH3HH5-Nonyloxytryptamine157798-12-4
[[File:2-Methyl-5-hydroxytryptamine.svg120pxclass=skin-invert-image]][2-Methyl-5-hydroxytryptamine](2-methyl-5-hydroxytryptamine)artificial2-CH3, 5-OHHH3-(2-aminoethyl)-2-methyl-1*H*-indol-5-ol78263-90-8
[[File:N-Ethyltryptamine.png120pxclass=skin-invert-image]]NETartificialHHCH2CH3N-ethyltryptamine61-53-0
[[File:NiPT_2D.svg120pxclass=skin-invert-image]]NiPTartificialHHCH(CH3)2N-isopropyltryptamine14121-10-9
[[File:NcPT_structure.png120pxclass=skin-invert-image]]NcPTartificialHHC3H5N-cyclopropyltryptamine
[[File:NsBT_2D.svg120pxclass=skin-invert-image]]NsBTartificialHHCH(CH3)CH2CH3N-*sec*-butyltryptamine
[[File:N-t-butyltryptamine.svg120pxclass=skin-invert-image]]NtBTartificialHHC(CH3)3N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine1344092-44-9
[[File:Amyltrytamine.svg120pxclass=skin-invert-image]]NATartificialHH(CH2)4CH3*N*-[2-(1*H*-indol-3-yl)ethyl]pentan-1-amine
[[File:N-Hexyltryptamine chemical structure.svg120pxclass=skin-invert-image]]NHTartificialHH(CH2)5CH3*N*-[2-(1*H*-indol-3-yl)ethyl]hexan-1-amine
[[File:Benzyltryptamine.svg130pxclass=skin-invert-image]]*N*-Benzyltryptamine (NBnT)artificialHHCH2C6H5*N*-benzyltryptamine15741-79-4
[[File:4-HO-NET.svg130pxclass=skin-invert-image]][4-HO-NET](4-ho-net)artificial4-OHCH2CH3H4-hydroxy-*N*-ethyltryptamine
[[File:4-HO-NPT.svg130pxclass=skin-invert-image]][4-HO-NPT](4-ho-npt)artificial4-OHCH(CH3)2H4-hydroxy-*N*-propyltryptamine
[[File:4-HO-NiPT.svg130pxclass=skin-invert-image]][4-HO-NiPT](4-ho-nipt)artificial4-OHCH(CH3)2H4-hydroxy-*N*-isopropyltryptamine
[[File:4-HO-NALT_2D.svg120pxclass=skin-invert-image]][4-HO-NALT](4-ho-nalt)artificial4-OHHH2C=CH-CH24-hydroxy-*N*-allyltryptamine
[[File:4-HO-NBT chemical structure.svg130pxclass=skin-invert-image]]4-HO-NBT (4-HO-NnBT)artificial4-OHH(CH2)3CH34-hydroxy-*N*-*n*-butyltryptamine
[[File:4-HO-NiBT chemical structure.svg130pxclass=skin-invert-image]]4-HO-NiBTartificial4-OHHCH2CH(CH3)24-hydroxy-*N*-isobutyltryptamine
[[File:4-HO-NsBT chemical structure.svg130pxclass=skin-invert-image]]4-HO-NsBTartificial4-OHHCH(CH3)CH2CH34-hydroxy-*N*-*sec*-butyltryptamine
[[File:4-HO-NtBT chemical structure.svg130pxclass=skin-invert-image]]4-HO-NtBTartificial4-OHHC(CH3)34-hydroxy-*N*-*tert*-butyltryptamine
[[File:4-HO-NBnT 2D.svg130pxclass=skin-invert-image]][4-HO-NBnT](4-ho-nbnt)artificial4-OHHCH2C6H54-hydroxy-*N*-benzyltryptamine
[[File:4-HO-NcHT chemical structure.svg130pxclass=skin-invert-image]]4-HO-NcHTartificial4-OHHC6H114-hydroxy-*N*-cyclohexyltryptamine
[[File:5-MeO-NET.svg120pxclass=skin-invert-image]][5-MeO-NET](5-meo-net)artificial5-OCH3HCH2CH35-methoxy-*N*-ethyltryptamine1019-46-1
[[File:5-MeO-NIPT.svg120pxclass=skin-invert-image]][5-MeO-NiPT](5-meo-nipt)artificial5-OCH3HCH(CH3)25-methoxy-*N*-isopropyltryptamine109921-55-3
[[File:5-MeO-NsBT.svg130pxclass=skin-invert-image]][5-MeO-NsBT](5-meo-nsbt)artificial5-OCH3HCH(CH3)CH2CH35-methoxy-*N*-*sec*-butyltryptamine
[[File:5-MeO-NBnT 2D.svg130pxclass=skin-invert-image]][5-MeO-NBnT](5-meo-nbnt)artificial5-OCH3HCH2C6H55-methoxy-*N*-benzyltryptamine25100-31-6
[[File:5-MeO-T-NBOMe_2D.svg130pxclass=skin-invert-image]][5-MeO-T-NBOMe](5-meo-t-nbome)artificial5-OCH3HCH2C6H4(*o*-OCH3)5-methoxy-*N*-(*ortho*-methoxybenzyl)tryptamine1335331-37-7
[[File:5MT-NB3OMe.svg130pxclass=skin-invert-image]]vauthors = Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BKtitle = 5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptaminesjournal = PLOS ONEvolume = 14issue = 1article-number = e0209804date = 2019pmid = 30629611pmc = 6328172doi = 10.1371/journal.pone.0209804bibcode = 2019PLoSO..1409804Tdoi-access = free }}artificial5-OCH3HCH2C6H4(*m*-OCH3)5-methoxy-*N*-(*meta*-methoxybenzyl)tryptamine1648553-42-7
[[File:5-Methoxy-N-(4-bromobenzyl)tryptamine).svg130pxclass=skin-invert-image]][5-MeO-NBpBrT](5-meo-nbpbrt)artificial5-OCH3HCH2C6H4(*p*-Br)N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine155639-13-7
[[File:5-MeO-34MPEMT_structure.png130pxclass=skin-invert-image]]5-MeO-34MPEMTartificial5-OCH3CH3CH2CH2C6H3(*p,m*-OCH3)N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
[[File:Lu-AE58054.svg130pxclass=skin-invert-image]]Idalopirdineartificial6-FHCH2C6H4(*m*-OCH2CF2CF2H)2-(6-Fluoro-1*H*-indol-3-yl)-*N*-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine467459-31-0
[[File:Z2876442907_structure.png130pxclass=skin-invert-image]]vauthors = Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, Barros-Álvarez X, Sakamoto K, Kim Y, DiBerto J, Kim K, Tummino TA, Huang S, Irwin JJ, Tarkhanova OO, Moroz Y, Skiniotis G, Kruse AC, Shoichet BK, Roth BLdisplay-authors = 6title = AlphaFold2 structures template ligand discoverydate = December 2023biorxiv = 10.1101/2023.12.20.572662 }}artificial4-CH3HCH2(C3HNS)-COOCH2CH3ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate
[[File:Cis-2',4'-dimethyl-4-HO-azt-T_structure.png120pxclass=skin-invert-image]]vauthors = Stirn J, Berger R, Hübner H, Gmeiner P, Klein CDtitle = Towards "unmakable" psychedelics: SAR exploration of psilocin analogs obtained by a HATU-mediated amide coupling strategyjournal = European Journal of Medicinal Chemistry Reportsvolume = 15article-number = 100278date = 2025doi = 10.1016/j.ejmcr.2025.100278doi-access = free }}artificial4-OH*cis*-(CHCH3)CH2(CHCH3)3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol
[[File:Pyr-T.svg120pxclass=skin-invert-image]]Pyr-TartificialH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1*H*-indole14008-96-9
[[File:4-HO-pyr-T.png120pxclass=skin-invert-image]][4-HO-pyr-T](4-ho-pyr-t)artificial4-OH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1*H*-indol-4-ol63097-26-7
[[File:Cis-2',5'-dimethyl-4-HO-pyr-T_structure.png120pxclass=skin-invert-image]]Cis-2',5'-dimethyl-4-HO-pyr-Tartificial4-OH*cis*-(CHCH3)CH2CH2(CHCH3)3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol
[[File:5-MeO-pyr-T.png120pxclass=skin-invert-image]][5-MeO-pyr-T](5-meo-pyr-t)artificial5-OCH3(CH2)45-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1*H*-indole3949-14-2
[[File:4-F-5-MeO-pyr-T.svg120pxclass=skin-invert-image]][4-F-5-MeO-pyr-T](4-f-5-meo-pyr-t)artificial4-F-5-OCH3(CH2)44-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1*H*-indole344790-93-8
[[File:Pip-Tryptamine.svg120pxclass=skin-invert-image]]Pip-TartificialH(CH2)53-(2-Piperidin-1-ylethyl)-1*H*-indole26628-87-5
[[File:5-MeO-pip-T.svg120pxclass=skin-invert-image]][5-MeO-pip-T](5-meo-pip-t)artificial5-OCH3(CH2)55-Methoxy-3-(2-piperidin-1-ylethyl)-1*H*-indole
[[File:Mor-Tryptamine chemical structure.svg120pxclass=skin-invert-image]]Mor-TartificialH?3-[2-(Morpholin-4-yl)ethyl]-1*H*-indole25262-59-3
[[File:5-MeO-mor-T chemical structure.svg120pxclass=skin-invert-image]][5-MeO-mor-T](5-meo-mor-t)artificial5-OCH3?5-Methoxy-3-[2-(morpholin-4-yl)ethyl]-1*H*-indole3949-13-1
[[File:IsoqT chemical structure.svg120pxclass=skin-invert-image]]IsoqTartificialH?3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-1*H*-indole
[[File:5-MeO-IsoqT.svg120pxclass=skin-invert-image]][5-MeO-IsoqT](5-meo-isoqt)artificial5-OCH3?3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-5-methoxy-1*H*-indole
[[File:Indolylethylfentanyl_structure.png120pxclass=skin-invert-image]]IndolylethylfentanylartificialH(CH2)5-4-N(COCH2CH3)C6H5N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide58399-46-5
[[File:MET_image.svg120pxclass=skin-invert-image]]METartificialHCH3CH2CH3N-Methyl-N-ethyltryptamine5599-69-9
[[File:Methylpropyltryptamine.svg120pxclass=skin-invert-image]]MPTartificialHCH3CH2CH2CH3N-Methyl-N-propyltryptamine850032-72-3
[[File:MIPT.svg120pxclass=skin-invert-image]]MiPTartificialHCH3CH(CH3)2N-Methyl-N-isopropyltryptamine96096-52-5
[[File:McPT_structure.png120pxclass=skin-invert-image]]McPTartificialHCH3C3H5N-Methyl-N-cyclopropyltryptamine1373918-63-8
[[File:EcPT_structure.png120pxclass=skin-invert-image]]EcPTartificialHCH2CH3C3H5N-ethyl-N-cyclopropyltryptamine
[[File:PcPT_structure.png120pxclass=skin-invert-image]]PcPTartificialHCH2CH2CH3C3H5N-propyl-N-cyclopropyltryptamine
[[File:iPcPT_structure.png120pxclass=skin-invert-image]]iPcPTartificialHCH(CH3)2C3H5N-isopropyl-N-cyclopropyltryptamine
[[File:DcPT_structure.png120pxclass=skin-invert-image]]DcPTartificialHC3H5C3H5N,N-dicyclopropyltryptamine1373918-62-7
[[File:MBT.svg120pxclass=skin-invert-image]]MBTartificialHCH3(CH2)3CH3N-Methyl-N-butyltryptamine848130-12-1
[[File:MSBT_structure.png120pxclass=skin-invert-image]]MsBTartificialHCH3CH(CH3)CH2CH3N-Methyl-N-*sec*-butyltryptamine
[[File:MiBT_structure.png120pxclass=skin-invert-image]]MiBTartificialHCH3CH2CH(CH3)2N-Methyl-N-*iso*-butyltryptamine
[[File:McPMT_structure.png120pxclass=skin-invert-image]]McPMTartificialHCH3CH2C3H5N-Methyl-N-(cyclopropylmethyl)tryptamine
[[File:Diethyltryptamine structure.svg120pxclass=skin-invert-image]]DETartificialHCH2CH3CH2CH3*N*,*N*-diethyltryptamine61-51-8
[[File:Ethylpropyltryptamine.svg120pxclass=skin-invert-image]]EPTartificialHCH2CH3CH2CH2CH3N-Ethyl-N-propyltryptamine850032-68-7
[[File:Ethylisopropyltryptamine.svg120pxclass=skin-invert-image]]EiPTartificialHCH2CH3CH(CH3)2N-Ethyl-N-isopropyltryptamine848130-11-0
[[File:DPT.svg120pxclass=skin-invert-image]]DPTartificialHCH2CH2CH3CH2CH2CH3*N*,*N*-dipropyltryptamine61-52-9
[[File:Propylisopropyltryptamine.svg120pxclass=skin-invert-image]]PiPTartificialHCH2CH2CH3CH(CH3)2N-Propyl-N-isopropyltryptamine1354632-00-0
[[File:DiPT.svg120pxclass=skin-invert-image]]DiPTartificialHCH(CH3)2CH(CH3)2*N*,*N*-diisopropyltryptamine14780-24-6
[[File:EBT_structure.png120pxclass=skin-invert-image]]EBTartificialHCH2CH3(CH2)3CH3N-ethyl-N-butyltryptamine
[[File:PBT_structure.png120pxclass=skin-invert-image]]PBTartificialHCH2CH2CH3(CH2)3CH3N-propyl-N-butyltryptamine
[[File:iPsBT_structure.png120pxclass=skin-invert-image]]iPsBTartificialHCH(CH3)2CH(CH3)CH2CH3N-isopropyl-N-sec-butyltryptamine
[[File:Dibutyltryptamine.svg120pxclass=skin-invert-image]]DBTartificialH(CH2)3CH3(CH2)3CH3*N*,*N*-dibutyltryptamine15741-77-2
[[File:DIBT_structure.png120pxclass=skin-invert-image]]DiBTartificialHCH2CH(CH3)2CH2CH(CH3)2*N*,*N*-diisobutyltryptamine63938-64-7
[[File:DSBT_structure.png120pxclass=skin-invert-image]]DsBTartificialHCH(CH3)CH2CH3CH(CH3)CH2CH3*N*,*N*-disecbutyltryptamine
[[File:Diamyltryptamine.svg120pxclass=skin-invert-image]]DATartificialH(CH2)4CH3(CH2)4CH3*N*,*N*-diamyltryptamine
[[File:Dihexyltryptamine.svg120pxclass=skin-invert-image]]DHTartificialH(CH2)5CH3(CH2)5CH3*N*,*N*-dihexyltryptamine
[[File:Methylallyltryptamine.svg120pxclass=skin-invert-image]]MALTartificialHCH3H2C=CH-CH2N-methyl-N-allyltryptamine1366416-29-6
[[File:DALT-structure.png120pxclass=skin-invert-image]]DALTartificialHH2C=CH-CH2H2C=CH-CH2*N*,*N*-diallyltryptamine60676-77-9
[[File:Propylallyltryptamine.svg120pxclass=skin-invert-image]]PALTartificialHH2C=CH-CH2CH2CH2CH3*N*-propyl-*N*-allyltryptamine2686297-71-0
[[File:IPALT.svg120pxclass=skin-invert-image]]iPALT (ALiPT)artificialHH2C=CH-CH2CH(CH3)2N-allyl-N-isopropyltryptamine
[[File:N-DEAOP-NMT chemical structure.svg120pxclass=skin-invert-image]]*N*-DEAOP-NMTartificialH?CH3*N*-(3-diethylamino-3-oxopropyl)-*N*-methyltryptamine
[[File:5-MeO-N-DEAOP-NMT chemical structure.svg120pxclass=skin-invert-image]][5-MeO-*N*-DEAOP-NMT](5-meo-n-deaop-nmt)artificial5-OCH3?CH3*N*-(3-diethylamino-3-oxopropyl)-*N*-methyl-5-methoxytryptamine
[[File:N-DEAOP-NET chemical structure.svg120pxclass=skin-invert-image]]*N*-DEAOP-NETartificialH?CH2CH3*N*-(3-diethylamino-3-oxopropyl)-*N*-ethyltryptamine
[[File:5-MeO-N-DEAOP-NET chemical structure.svg120pxclass=skin-invert-image]][5-MeO-*N*-DEAOP-NET](5-meo-n-deaop-net)artificial5-OCH3?CH2CH3*N*-(3-diethylamino-3-oxopropyl)-*N*-ethyl-5-methoxytryptamine
[[File:1-Methyl-DMT.svg120pxclass=skin-invert-image]][1-Methyl-DMT](1-methyl-dmt)artificial1-CH3CH3CH31-methyl-*N*,*N*-dimethyltryptamine13366-47-7
[[File:2-Me-DMT.svg120pxclass=skin-invert-image]][2-Methyl-DMT](2-n-n-tmt)artificial2-CH3CH3CH3(2-(2-methyl-1*H*-indol-3-yl)-1-methyl-ethyl)dimethylamine1080-95-1
[[File:2-methyl-diethyltryptamine.png120pxclass=skin-invert-image]][2-Methyl-DET](2-me-det)artificial2-CH3CH2CH3CH2CH3*N*,*N*-Diethyl-2-(2-methyl-1*H*-indol-3-yl)ethan-1-amine26628-88-6
[[File:2-Methyl-DiPT chemical structure.svg120pxclass=skin-invert-image]][2-Methyl-DiPT](2-methyl-dipt)artificial2-CH3CH(CH3)2CH(CH3)22-methyl-*N*,*N*-diisopropyltryptamine
[[File:2-Methyl-iPALT.svg120pxclass=skin-invert-image]][2-Methyl-iPALT](2-methyl-ipalt)artificial2-CH3CH(CH3)2H2C=CH-CH22-methyl-*N*-isopropyl-*N*-allyltryptamine2915652-49-0
[[File:4-Amino-DMT_structure.png120pxclass=skin-invert-image]]4-Amino-DMTartificial4-NH2CH3CH34-amino-*N*,*N*-dimethyltryptamine60331-61-5
[[File:4-Me-DMT_structure.png120pxclass=skin-invert-image]][4-Methyl-DMT](4-methyl-dmt)artificial4-CH3CH3CH34,*N*,*N*-trimethyltryptamine28289-23-8
[[File:4-MeO-DMT chemical structure.svg120pxclass=skin-invert-image]][4-MeO-DMT](4-meo-dmt)artificial4-OCH3CH3CH34-methoxy-*N*,*N*-dimethyltryptamine3965-97-7
[[File:4-MeO-DET.svg120pxclass=skin-invert-image]][4-MeO-DET](4-meo-det)artificial4-OCH3CH2CH3CH2CH34-methoxy-*N*,*N*-diethyltryptamine
[[File:4-MeO-MiPT.png120pxclass=skin-invert-image]][4-MeO-MiPT](4-meo-mipt)artificial4-OCH3CH3CH(CH3)24-methoxy-N-methyl-N-isopropyltryptamine96096-53-6
[[File:4-MeO-DiPT.svg120pxclass=skin-invert-image]][4-MeO-DiPT](4-meo-dipt)artificial4-OCH3CH(CH3)2CH(CH3)24-methoxy-N,N-diisopropyltryptamine
[[File:O-Acetylpsilocin_chemical_structure.png120pxclass=skin-invert-image]][4-AcO-DMT](4-aco-dmt)artificial4-OCOCH3CH3CH34-acetoxy-*N*,*N*-dimethyltryptamine92292-84-7
[[File:4-PrO-DMT.svg120pxclass=skin-invert-image]][4-PrO-DMT](4-pro-dmt)artificial4-OCOCH2CH3CH3CH34-propionyloxy-*N*,*N*-dimethyltryptamine1373882-11-1
[[File:RE-109.svg120pxclass=skin-invert-image]][4-GO-DMT](4-go-dmt) (RE109; FT-109)artificial4-OCO(CH2)3COOHCH3CH34-glutaryloxy-N,N-dimethyltryptamine
[[File:4-HO-MET.svg120pxclass=skin-invert-image]][4-HO-MET](4-ho-met)artificial4-OHCH3CH2CH34-hydroxy-N-methyl-N-ethyltryptamine77872-41-4
[[File:4-Acetoxy-N-methyl-N-ethyltryptamine.svg120pxclass=skin-invert-image]][4-AcO-MET](4-aco-met)artificial4-OCOCH3CH3CH2CH34-acetoxy-N-methyl-N-ethyltryptamine1445751-40-5
[[File:4-PrO-MET.svg120pxclass=skin-invert-image]][4-PrO-MET](4-pro-met)artificial4-OCOCH2CH3CH3CH2CH34-propionyloxy-N-methyl-N-ethyltryptamine
[[File:4-PO-MET_structure.png120pxclass=skin-invert-image]]4-PO-METartificial4-OPO3H2CH3CH2CH34-phosphoryloxy-N-methyl-N-ethyltryptamine
[[File:4-HO-DET.svg120pxclass=skin-invert-image]][4-HO-DET](4-ho-det)artificial4-OHCH2CH3CH2CH34-hydroxy-*N*,*N*-diethyltryptamine22204-89-3
[[File:4-Acetoxy-DET.png120pxclass=skin-invert-image]][4-AcO-DET](4-aco-det)artificial4-OCOCH3CH2CH3CH2CH34-acetoxy-N,N-diethyltryptamine1135424-15-5
[[File:Ethocybin.png120pxclass=skin-invert-image]]4-PO-DETartificial4-OPO3H2CH2CH3CH2CH34-phosphoryloxy-N,N-diethyltryptamine60480-02-6
[[File:4-Hydroxy-N-ethyl-N-propyltryptamine.svg120pxclass=skin-invert-image]][4-HO-EPT](4-ho-ept)artificial4-OHCH2CH3CH2CH2CH34-hydroxy-N-ethyl-N-propyltryptamine2595431-59-5
[[File:4-AcO-EPT.svg120pxclass=skin-invert-image]][4-AcO-EPT](4-aco-ept)artificial4-OCOCH3CH2CH3CH2CH2CH34-acetoxy-N-ethyl-N-propyltryptamine2750249-90-0
[[File:4-PO-EPT_structure.png120pxclass=skin-invert-image]]4-PO-EPTartificial4-OPO3H2CH2CH3CH2CH2CH34-phosphoryloxy-N-ethyl-N-propyltryptamine
[[File:4-AcO-EiPT Structure.svg120pxclass=skin-invert-image]][4-AcO-EiPT](4-aco-eipt)artificial4-OCOCH3CH2CH3CH(CH3)24-acetoxy-N-ethyl-N-isopropyltryptamine
[[File:4-HO-MPT.svg120pxclass=skin-invert-image]][4-HO-MPT](4-ho-mpt)artificial4-OHCH3CH2CH2CH34-hydroxy-N-methyl-N-propyltryptamine763035-03-6
[[File:4-HO-MiPT.svg120pxclass=skin-invert-image]][4-HO-MiPT](4-ho-mipt)artificial4-OHCH(CH3)2CH34-hydroxy-*N*-isopropyl-*N*-methyltryptamine77872-43-6
[[File:4-Acetoxy-MiPT.svg120pxclass=skin-invert-image]][4-AcO-MiPT](4-aco-mipt)artificial4-OCOCH3CH3CH(CH3)24-acetoxy-N-methyl-N-isopropyltryptamine1024612-25-6
[[File:4-HO-MALT structure.png120pxclass=skin-invert-image]]vauthors = Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt ALtitle = Investigation of the Structure-Activity Relationships of Psilocybin Analoguesjournal = ACS Pharmacology & Translational Sciencevolume = 4issue = 2pages = 533–542date = April 2021pmid = 33860183pmc = 8033608doi = 10.1021/acsptsci.0c00176 }}artificial4-OHCH3H2C=CH-CH24-hydroxy-N-methyl-N-allyltryptamine
[[File:4-AcO-MALT structure.png120pxclass=skin-invert-image]]vauthors = Pham DN, Chadeayne AR, Golen JA, Manke DRtitle = Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrugjournal = Acta Crystallographica Section Evolume = 77issue = Pt 2pages = 101–106date = February 2021pmid = 33614134pmc = 7869532doi = 10.1107/S2056989021000116doi-access = freebibcode = 2021AcCrE..77..101P }}artificial4-OCOCH3CH3H2C=CH-CH24-acetoxy-N-Methyl-N-allyltryptamine
[[File:4-HO-iPALT chemical structure.svg120pxclass=skin-invert-image]]4-HO-iPALTartificial4-OHCH(CH3)2H2C=CH-CH24-hydroxy-*N*-isopropyl-*N*-allyltryptamine
[[File:4-HO-MBT.svg120pxclass=skin-invert-image]][4-HO-MBT](4-ho-mbt)artificial4-OH(CH2)3CH3CH34-hydroxy-*N*-butyl-*N*-methyltryptamine
[[File:4-HO-MSBT_structure.png120pxclass=skin-invert-image]][4-HO-MsBT](4-ho-msbt)artificial4-OHCH(CH3)CH2CH3CH34-hydroxy-*N*-*sec*-butyl-*N*-methyltryptamine
[[File:4-HO-MtBT chemical structure.svg120pxclass=skin-invert-image]][4-HO-MtBT](4-ho-mtbt)artificial4-OHC(CH3)3CH34-hydroxy-*N*-*tert*-butyl-*N*-methyltryptamine
[[File:4-HO-EiBT_2D.svg120pxclass=skin-invert-image]][4-HO-EiBT](4-ho-eibt)artificial4-OHCH2CH(CH3)2CH2CH34-hydroxy-*N*-*iso*-butyl-*N*-ethyltryptamine
[[File:4-HO-McPT.svg120pxclass=skin-invert-image]][4-HO-McPT](4-ho-mcpt)artificial4-OHC3H5CH34-hydroxy-*N*-cyclopropyl-*N*-methyltryptamine2883663-05-4
[[File:4-AcO-McPT.svg120pxclass=skin-invert-image]][4-AcO-McPT](4-aco-mcpt)artificial4-OCOCH3C3H5CH34-acetoxy-*N*-cyclopropyl-*N*-methyltryptamine
[[File:4-HO-McPeT.svg120pxclass=skin-invert-image]][4-HO-McPeT](4-ho-mcpet)artificial4-OHC5H9CH34-hydroxy-*N*-cyclopentyl-*N*-methyltryptamine77872-48-1
[[File:4-HO-McPMT structure.png120pxclass=skin-invert-image]]4-HO-McPMTartificial4-OHCH2C3H5CH34-hydroxy-*N*-cyclopropylmethyl-*N*-methyltryptamine
[[File:4-HO-DPT.svg120pxclass=skin-invert-image]][4-HO-DPT](4-ho-dpt)artificial4-OHCH2CH2CH3CH2CH2CH34-hydroxy-*N*,*N*-dipropyltryptamine63065-88-3
[[File:4-AcO-DPT Structure.svg120pxclass=skin-invert-image]][4-AcO-DPT](4-aco-dpt)artificial4-OCOCH3CH2CH2CH3CH2CH2CH34-acetoxy-N,N-dipropyltryptamine1445751-75-6
[[File:4-HO-PiPT.svg120pxclass=skin-invert-image]][4-HO-PiPT](4-ho-pipt)artificial4-OHCH2CH2CH3CH(CH3)24-hydroxy-*N*-propyl-*N*-isopropyltryptamine
[[File:4-AcO-PiPT_structure.png120pxclass=skin-invert-image]]4-AcO-PiPTartificial4-OCOCH3CH2CH2CH3CH(CH3)24-acetoxy-*N*-propyl-*N*-isopropyltryptamine
[[File:4-HO-DIPT.SVG120pxclass=skin-invert-image]][4-HO-DiPT](4-ho-dipt)artificial4-OHCH(CH3)2CH(CH3)24-hydroxy-*N*,*N*-diisopropyltryptamine132328-45-1
[[File:4-AcO-DiPT.svg120pxclass=skin-invert-image]][4-AcO-DiPT](4-aco-dipt)artificial4-OCOCH3CH(CH3)2CH(CH3)24-acetoxy-N,N-diisopropyltryptamine936015-60-0
[[File:4-PrO-DiPT structure.png120pxclass=skin-invert-image]][4-PrO-DiPT](4-pro-dipt)artificial4-OCOCH2CH3CH(CH3)2CH(CH3)24-propionyloxy-N,N-diisopropyltryptamine1373882-13-3
[[File:Luvesilocin.svg120pxclass=skin-invert-image]]Luvesilocin (RE104; FT-104)artificial4-OCO(CH2)3COOHCH(CH3)2CH(CH3)24-glutaryloxy-N,N-diisopropyltryptamine
[[File:4-PO-DiPT_structure.png120pxclass=skin-invert-image]]4-PO-DiPTartificial4-OPO3H2CH(CH3)2CH(CH3)24-phosphoryloxy-N,N-diisopropyltryptamine1373882-09-7
[[File:4-HO-DALT 2D.svg120pxclass=skin-invert-image]][4-HO-DALT](4-ho-dalt)artificial4-OHH2C=CH-CH2H2C=CH-CH24-hydroxy-N,N-diallyltryptamine2173386-70-2
[[File:4-AcO-DALT.svg120pxclass=skin-invert-image]][4-AcO-DALT](4-aco-dalt)artificial4-OCOCH3H2C=CH-CH2H2C=CH-CH24-acetoxy-N,N-diallyltryptamine1445751-71-2
[[File:4-HO-DBT.svg120pxclass=skin-invert-image]][4-HO-DBT](4-ho-dbt)artificial4-OH(CH2)3CH3(CH2)3CH34-hydroxy-*N*,*N*-dibutyltryptamine63065-89-4
[[File:4-HO-DIBT_structure.png120pxclass=skin-invert-image]][4-HO-DiBT](4-ho-dibt)artificial4-OHCH2CH(CH3)2CH2CH(CH3)24-hydroxy-*N*,*N*-diisobutyltryptamine
[[File:4-HO-DSBT.svg120pxclass=skin-invert-image]][4-HO-DsBT](4-ho-dsbt)artificial4-OHCH(CH3)CH2CH3CH(CH3)CH2CH34-hydroxy-*N*,*N*-disecbutyltryptamine127507-01-1
[[File:5-MeO-MET.svg120pxclass=skin-invert-image]][5-MeO-MET](5-meo-met)artificial5-OCH3CH2CH3CH35-methoxy-*N*-methyl-*N*-ethyltryptamine16977-53-0
[[File:5-MeO-DET.svg120pxclass=skin-invert-image]][5-MeO-DET](5-meo-det)artificial5-OCH3CH2CH3CH2CH35-methoxy-*N*,*N*-diethyltryptamine2454-70-8
[[File:5-MeO-MPT 2D.svg120pxclass=skin-invert-image]][5-MeO-MPT](5-meo-mpt)artificial5-OCH3CH3CH2CH2CH35-methoxy-*N*-methyl-*N*-propyltryptamine
[[File:5-MeO-EPT.svg120pxclass=skin-invert-image]][5-MeO-EPT](5-meo-ept)artificial5-OCH3CH2CH3CH2CH2CH35-methoxy-*N*-ethyl-*N*-propyltryptamine850032-67-6
[[File:5-MeO-DPT.svg120pxclass=skin-invert-image]][5-MeO-DPT](5-meo-dpt)artificial5-OCH3CH2CH2CH3CH2CH2CH35-methoxy-*N*,*N*-dipropyltryptamine69496-75-9
[[File:5-MeO-MALT.png120pxclass=skin-invert-image]][5-MeO-MALT](5-meo-malt)artificial5-OCH3H2C=CH-CH2CH35-methoxy-*N*-Methyl-*N*-allyltryptamine1373918-64-9
[[File:5-MeO-DALT.svg120pxclass=skin-invert-image]][5-MeO-DALT](5-meo-dalt)artificial5-OCH3H2C=CH-CH2H2C=CH-CH25-methoxy-*N*,*N*-diallyltryptamine928822-98-4
[[File:5-MeO-iPALT 2D.svg120pxclass=skin-invert-image]]ASR-3001 (5-MeO-iPALT)artificial5-OCH3H2C=CH-CH2CH2CH(CH3)25-methoxy-N-allyl-N-isopropyltryptamine
[[File:5-MeO-MiPT.svg120pxclass=skin-invert-image]][5-MeO-MiPT](5-meo-mipt)artificial5-OCH3CH3CH(CH3)25-methoxy-*N*,*N*-methylisopropyltryptamine96096-55-8
[[File:5,6-MeO-MiPT.svg120pxclass=skin-invert-image]][5,6-MeO-MiPT](5-6-meo-mipt)artificial5-OCH3, 6-OCH3CH3CH(CH3)25,6-dimethoxy-*N*,*N*-methylisopropyltryptamine
[[File:5-MeO-MsBT.svg120pxclass=skin-invert-image]][5-MeO-MsBT](5-meo-msbt)artificial5-OCH3CH3CH(CH3)CH2CH35-methoxy-*N*-methyl-*N*-*sec*-butyltryptamine
[[File:5-MeO-McPT_structure.png120pxclass=skin-invert-image]]5-MeO-McPTartificial5-OCH3CH3C3H55-methoxy-*N*-methyl-*N*-cyclopropyltryptamine
[[File:5-MeO-McBT_structure.png120pxclass=skin-invert-image]]5-MeO-McBTartificial5-OCH3CH3C4H75-methoxy-*N*-methyl-*N*-cyclobutyltryptamine
[[File:5-MeO-EiPT_structure.png120pxclass=skin-invert-image]][5-MeO-EiPT](5-meo-eipt)artificial5-OCH3CH2CH3CH(CH3)25-methoxy-N-ethyl-N-isopropyltryptamine850032-66-5
[[File:5-MeO-PiPT.svg120pxclass=skin-invert-image]][5-MeO-PiPT](5-meo-pipt)artificial5-OCH3CH2CH2CH3CH(CH3)25-methoxy-*N*-propyl-*N*-isopropyltryptamine
[[File:5-MeO-DiPT.svg120pxclass=skin-invert-image]][5-MeO-DiPT](5-meo-dipt)artificial5-OCH3CH(CH3)2CH(CH3)25-methoxy-*N*,*N*-diisopropyltryptamine4021-34-5
[[File:5-MeO-DBT.svg120pxclass=skin-invert-image]][5-MeO-DBT](5-meo-dbt)artificial5-OCH3(CH2)3CH3(CH2)3CH35-methoxy-*N*,*N*-dibutyltryptamine73785-42-9
[[File:5-MeO-DsBT_structure.png120pxclass=skin-invert-image]][5-MeO-DsBT](5-meo-dsbt)artificial5-OCH3CH(CH3)CH2CH3CH(CH3)CH2CH35-methoxy-*N*,*N*-di-*sec*-butyltryptamine
[[File:5-MeS-DMT.svg120pxclass=skin-invert-image]][5-MeS-DMT](5-mes-dmt)artificial5-SCH3CH3CH35-methylthio-*N*,*N*-dimethyltryptamine5102-11-4
[[File:5-AcO-DMT.svg120pxclass=skin-invert-image]]5-AcO-DMTartificial5-OCOCH3CH3CH35-acetoxy-*N*,*N*-dimethyltryptamine16977-50-7
[[File:5-AcO-MET_structure.png120pxclass=skin-invert-image]]5-AcO-METartificial5-OCOCH3CH3CH2CH35-acetoxy-N-methyl-N-ethyltryptamine
[[File:5-AcO-DET_structure.png120pxclass=skin-invert-image]]5-AcO-DETartificial5-OCOCH3CH2CH3CH2CH35-acetoxy-*N*,*N*-diethyltryptamine
[[File:5-AcO-EPT_structure.png120pxclass=skin-invert-image]]5-AcO-EPTartificial5-OCOCH3CH2CH3CH2CH2CH35-acetoxy-N-ethyl-N-propyltryptamine
[[File:5-AcO-DPT_structure.png120pxclass=skin-invert-image]]5-AcO-DPTartificial5-OCOCH3CH2CH2CH3CH2CH2CH35-acetoxy-*N*,*N*-dipropyltryptamine
[[File:5-AcO-MiPT_structure.png120pxclass=skin-invert-image]]5-AcO-MiPTartificial5-OCOCH3CH3CH(CH3)25-acetoxy-N-methyl-N-isopropyltryptamine
[[File:5-AcO-DiPT_structure.png120pxclass=skin-invert-image]]5-AcO-DiPTartificial5-OCOCH3CH(CH3)2CH(CH3)25-acetoxy-*N*,*N*-diisopropyltryptamine
[[File:5-EtO-DMT Structure.svg120pxclass=skin-invert-image]][5-Ethoxy-DMT](5-ethoxy-dmt)artificial5-OCH2CH3CH3CH35-ethoxy-*N*,*N*-dimethyltryptamine855245-09-9
[[File:5-EtO-MET_structure.png120pxclass=skin-invert-image]]5-Ethoxy-METartificial5-OCH2CH3CH3CH2CH35-ethoxy-N-methyl-N-ethyltryptamine
[[File:5-EtO-DET_structure.png120pxclass=skin-invert-image]]5-Ethoxy-DETartificial5-OCH2CH3CH2CH3CH2CH35-ethoxy-N,N-diethyltryptamine
[[File:5-EtO-MPT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-MPTartificial5-OCH2CH3CH3CH2CH2CH35-ethoxy-N-methyl-N-propyltryptamine
[[File:5-EtO-EPT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-EPTartificial5-OCH2CH3CH2CH3CH2CH2CH35-ethoxy-N-ethyl-N-propyltryptamine
[[File:5-EtO-DPT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-DPTartificial5-OCH2CH3CH2CH2CH3CH2CH35-ethoxy-N,N-dipropyltryptamine
[[File:5-EtO-MiPT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-MiPTartificial5-OCH2CH3CH3CH(CH3)25-ethoxy-N-methyl-N-isopropyltryptamine
[[File:5-EtO-EiPT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-EiPTartificial5-OCH2CH3CH2CH3CH(CH3)25-ethoxy-N-ethyl-N-isopropyltryptamine
[[File:5-EtO-DiPT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-DiPTartificial5-OCH2CH3CH(CH3)2CH(CH3)25-ethoxy-N,N-diisopropyltryptamine
[[File:5-EtO-DALT_structure.png120pxclass=skin-invert-image]]5-Ethoxy-DALTartificial5-OCH2CH3H2C=CH-CH2H2C=CH-CH25-ethoxy-N,N-diallyltryptamine
[[File:5-BnO-DMT_structure.png120pxclass=skin-invert-image]]5-BnO-DMTartificial5-OCH2C6H5CH3CH35-benzyloxy-*N*,*N*-dimethyltryptamine101832-88-6
[[File:5-OH-MET.svg120pxclass=skin-invert-image]][5-HO-MET](5-ho-met)artificial5-OHCH3CH2CH35-hydroxy-*N*-methyl-*N*-ethyltryptamine
[[File:5-HO-DET 2D.svg120pxclass=skin-invert-image]][5-HO-DET](5-ho-det)artificial5-OHCH2CH3CH2CH35-hydroxy-*N*,*N*-diethyltryptamine14009-42-8
[[File:dipropylserotonin.svg120pxclass=skin-invert-image]][5-HO-DPT](5-ho-dpt)artificial5-OHCH2CH2CH3CH2CH2CH35-hydroxy-*N*,*N*-dipropyltryptamine36288-75-2
[[File:5-HO-MiPT structure.png120pxclass=skin-invert-image]]5-HO-MiPTartificial5-OHCH3CH(CH3)25-hydroxy-N-methyl-N-isopropyltryptamine
[[File:5-HO-DiPT.svg120pxclass=skin-invert-image]][5-HO-DiPT](5-ho-dipt)artificial5-OHCH(CH3)2CH(CH3)25-hydroxy-*N*,*N*-diisopropyltryptamine36288-76-3
[[File:5,N,N-TMT.svg120pxclass=skin-invert-image]][5-Methyl-DMT](5-n-n-tmt) (5,*N*,*N*-TMT)artificial5-CH3CH3CH35,*N*,*N*-trimethyltryptamine22120-39-4
[[File:5-Ethyl-DMT.svg120pxclass=skin-invert-image]][5-Ethyl-DMT](5-ethyl-dmt)artificial5-CH2CH3CH3CH35-ethyl-*N*,*N*-dimethyltryptamine171783-25-8
[[File:5-iPr-DMT_structure.png120pxclass=skin-invert-image]]5-Isopropyl-DMTartificial5-CH(CH3)2CH3CH35-isopropyl-*N*,*N*-dimethyltryptamine156281-04-8
[[File:5-tBu-DMT_structure.png120pxclass=skin-invert-image]]vauthors = Xu YC, Schaus JM, Walker C, Krushinski J, Adham N, Zgombick JM, Liang SX, Kohlman DT, Audia JEtitle = N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonistjournal = Journal of Medicinal Chemistryvolume = 42issue = 3pages = 526–31date = February 1999pmid = 9986723doi = 10.1021/jm9805945 }}artificial5-C(CH3)3CH3CH35-(*tert*-butyl)-*N*,*N*-dimethyltryptamine
[[File:5-Fluoro-DMT_structure.png120pxclass=skin-invert-image]][5-Fluoro-DMT](5-fluoro-dmt)artificial5-FCH3CH35-fluoro-*N*,*N*-dimethyltryptamine22120-36-1
[[File:5-F-MET.svg120pxclass=skin-invert-image]]Bretisilocin (5-fluoro-MET; GM-2505)artificial5-FCH3CH2CH35-fluoro-N-methyl-N-ethyltryptamine2698331-35-8
[[File:5-Fluoro-DET.svg120pxclass=skin-invert-image]][5-Fluoro-DET](5-fluoro-det)artificial5-FCH2CH3CH2CH35-fluoro-*N*,*N*-diethyltryptamine
[[File:5-Fluoro-EPT.svg120pxclass=skin-invert-image]][5-Fluoro-EPT](5-fluoro-ept)artificial5-FCH2CH3CH2CH2CH35-fluoro-N-ethyl-N-propyltryptamine
[[File:5-F-DPT_structure.png120pxclass=skin-invert-image]]5-Fluoro-DPTartificial5-FCH2CH2CH3CH2CH2CH35-fluoro-*N*,*N*-dipropyltryptamine
[[File:5F-PiPT_structure.png120pxclass=skin-invert-image]]5-Fluoro-PiPTartificial5-FCH2CH2CH3CH(CH3)25-fluoro-*N*-propyl-*N*-isopropyltryptamine
[[File:5F-PcBT_structure.png120pxclass=skin-invert-image]]5-Fluoro-PcBTartificial5-FCH2CH2CH3CH(CH2)35-fluoro-*N*-propyl-*N*-cyclobutyltryptamine
[[File:5F-iPcBT_structure.png120pxclass=skin-invert-image]]5-Fluoro-iPcBTartificial5-FCH(CH3)2CH(CH2)35-fluoro-*N*-isopropyl-*N*-cyclobutyltryptamine
[[File:5-F-DiPT_structure.png120pxclass=skin-invert-image]]5-Fluoro-DiPTartificial5-FCH(CH3)2CH(CH3)25-fluoro-*N*,*N*-diisoproptryptamine
[[File:5F-sBALT_structure.png120pxclass=skin-invert-image]]5-Fluoro-sBALTartificial5-FCH(CH3)CH2CH3CH2CH=CH25-fluoro-N-*sec*-butyl-N-allyltryptamine
[[File:5F-M1MALT_structure.png120pxclass=skin-invert-image]]5-Fluoro-M1MALTartificial5-FCH3CH(CH3)CH=CH25-fluoro-N-methyl-N-(1-methylallyl)tryptamine
[[File:5-Chloro-DMT.svg120pxclass=skin-invert-image]][5-Chloro-DMT](5-chloro-dmt)artificial5-ClCH3CH35-chloro-*N*,*N*-dimethyltryptamine22120-32-7
[[File:5-I-DMT_structure.png120pxclass=skin-invert-image]]5-Iodo-DMTartificial5-ICH3CH35-iodo-*N*,*N*-dimethyltryptamine22120-38-3
[[File:5-TFM-DMT 2D.svg120pxclass=skin-invert-image]][5-TFM-DMT](5-tfm-dmt)artificial5-CF3CH3CH35-(trifluoromethyl)-*N*,*N*-dimethyltryptamine2418713-32-1
[[File:5-TFMO-DMT 2D.svg120pxclass=skin-invert-image]][5-TFMO-DMT](5-tfmo-dmt)artificial5-OCF3CH3CH35-(trifluoromethoxy)-*N*,*N*-dimethyltryptamine
[[File:5-Nitro-DMT 2D.svg120pxclass=skin-invert-image]][5-Nitro-DMT](5-nitro-dmt)artificial5-NO2CH3CH35-nitro-*N*,*N*-dimethyltryptamine69937-13-9
[[File:5-CN-DMT_structure.png120pxclass=skin-invert-image]]5-CN-DMTartificial5-C≡NCH3CH35-cyano-*N*,*N*-dimethyltryptamine17380-42-6
[[File:5-CN-DPT_structure.png120pxclass=skin-invert-image]]5-CN-DPTartificial5-C≡NCH2CH2CH3CH2CH2CH35-cyano-*N*,*N*-dipropyltryptamine74885-19-1
[[File:Almotriptan skeletal.svg120pxclass=skin-invert-image]]Almotriptanartificial5-(CH2SO2N(CH2)4)CH3CH3*N*,*N*-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1*H*-indol-3-yl]-ethanamine154323-57-6
[[File:Rizatriptan Structural Formula V.1.svg120pxclass=skin-invert-image]]Rizatriptanartificial5-(CH2(N3(CH)2))CH3CH3*N*,*N*-dimethyl-2-[5-(1*H*-1,2,4-triazol-1-ylmethyl)-1*H*-indol-3-yl]ethanamine145202-66-0
[[File:Sumatriptan.svg120pxclass=skin-invert-image]]Sumatriptanartificial5-(CH2SO2NHCH3)CH3CH31-[3-(2-Dimethylaminoethyl)-1*H*-indol-5-yl]-*N*-methyl-methanesulfonamide103628-46-2
[[File:Zolmitriptan.svg120pxclass=skin-invert-image]]Zolmitriptanartificial5-(CHNHC=OOCH2)CH3CH35-( 4-(*S*)-1,3-oxazolidin-2-one)-*N*,*N*-dimethyltryptamine139264-17-8
[[File:6-Fluoro-DMT skeletal.svg120pxclass=skin-invert-image]][6-Fluoro-DMT](6-fluoro-dmt)artificial6-FCH3CH36-fluoro-*N*,*N*-dimethyltryptamine1511-31-5
[[File:6-Fluoro-DET.svg120pxclass=skin-invert-image]]vauthors = Rabin RA, Regina M, Doat M, Winter JCtitle = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogensjournal = Pharmacology, Biochemistry, and Behaviorvolume = 72issue = 1–2pages = 29–37date = May 2002pmid = 11900766doi = 10.1016/s0091-3057(01)00720-1s2cid = 6480715 }}artificial6-FCH2CH3CH2CH36-fluoro-*N*,*N*-diethyltryptamine2836-69-3
[[File:6-Cl-DMT_structure.png120pxclass=skin-invert-image]]6-Chloro-DMTartificial6-ClCH3CH36-chloro-*N*,*N*-dimethyltryptamine25390-72-1
[[File:6-Me-DMT_structure.png120pxclass=skin-invert-image]][6-Methyl-DMT](6-methyl-dmt)artificial6-CH3CH3CH36,*N*,*N*-trimethyltryptamine
[[File:6-Hydroxy-DMT.svg120pxclass=skin-invert-image]][6-Hydroxy-DMT](6-hydroxy-dmt)artificial6-OHCH3CH36-hydroxy-*N*,*N*-dimethyltryptamine1476-33-1
[[File:6-HO-DET 2D.svg120pxclass=skin-invert-image]][6-Hydroxy-DET](6-hydroxy-det)artificial6-OHCH3CH36-hydroxy-*N*,*N*-diethyltryptamine1476-59-1
[[File:6-MeO-DMT.svg120pxclass=skin-invert-image]][6-Methoxy-DMT](6-methoxy-dmt)artificial6-OCH3CH3CH36-methoxy-*N*,*N*-dimethyltryptamine2426-88-2
[[File:7-TMT_structure.png120pxclass=skin-invert-image]][7-Methyl-DMT](7-n-n-tmt)artificial7-CH3CH3CH37,*N*,*N*-trimethyltryptamine65882-39-5
[[File:7-Et-DMT_structure.png120pxclass=skin-invert-image]]7-Ethyl-DMTartificial7-CH2CH3CH3CH37-ethyl-*N*,*N*-dimethyltryptamine
[[File:7-Cl-DMT_structure.png120pxclass=skin-invert-image]]7-Chloro-DMTartificial7-ClCH3CH37-chloro-*N*,*N*-dimethyltryptamine
[[File:7-Br-DMT_structure.png120pxclass=skin-invert-image]]vauthors = Glennon RA, Schubert E, Jacyno JM, Rosecrans JAtitle = Studies on several 7-substituted N,N-dimethyltryptaminesjournal = Journal of Medicinal Chemistryvolume = 23issue = 11pages = 1222–6date = November 1980pmid = 6779006doi = 10.1021/jm00185a014 }}artificial7-BrCH3CH37-bromo-*N*,*N*-dimethyltryptamine74798-68-8
[[File:7-Hydroxy-DMT.svg120pxclass=skin-invert-image]][7-Hydroxy-DMT](7-hydroxy-dmt)artificial7-OHCH3CH37-hydroxy-*N*,*N*-dimethyltryptamine7578-26-9
[[File:7-MeO-DMT.svg120pxclass=skin-invert-image]][7-Methoxy-DMT](7-methoxy-dmt)artificial7-OCH3CH3CH37-methoxy-*N*,*N*-dimethyltryptamine
[[File:7-MeO-MiPT_structure.png120pxclass=skin-invert-image]]7-Methoxy-MiPTartificial7-OCH3CH3CH(CH3)27-methoxy-*N*-methyl-*N*-isopropyltryptamine
[[File:1-Methylpsilocin.svg120pxclass=skin-invert-image]][1-Methylpsilocin](1-methylpsilocin)artificial1-CH3, 4-OHCH3CH31-Methyl-3-[2-(*N*,*N*-dimethylamino)ethyl]-4-hydroxyindole1465-16-3
[[File:1-Me-5-MeO-DiPT.svg120pxclass=skin-invert-image]]1-Methyl-5-MeO-DiPTartificial1-CH3, 5-OCH3CH(CH3)2CH(CH3)21-methyl-5-methoxy-*N*,*N*-diisopropyltryptamine1373882-10-0
[[File:NB-DMT.svg100pxclass=skin-invert-image]]NBoc-DMT (NB-DMT)artificial1-OCOC(CH3)3CH3CH31-(t-butoxycarbonyl)-N,N-dimethyltryptamine
[[File:NB-5-MeO-MiPT_structure.png120pxclass=skin-invert-image]]NB-5-MeO-MiPTartificial1-OCOC(CH3)3, 5-OCH3CH3CH(CH3)21-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
[[File:NB-5-MeO-DALT_structure.png120pxclass=skin-invert-image]]NB-5-MeO-DALTartificial1-OCOC(CH3)3, 5-OCH3H2C=CH-CH2H2C=CH-CH21-(t-butoxycarbonyl)-5-methoxy-*N*,*N*-diallyltryptamine
[[File:6-Fluoropsilocin_structure.png120pxclass=skin-invert-image]]6-Fluoropsilocinartificial4-OH,6-FCH3CH34-hydroxy-6-fluoro-N,N-dimethyltryptamine312314-12-8
[[File:6F-5-MeO-DMT_structure.png120pxclass=skin-invert-image]]6-Fluoro-5-MeO-DMTartificial5-OCH3,6-FCH3CH35-methoxy-6-fluoro-N,N-dimethyltryptamine
[[File:56DF-EPT_structure.png120pxclass=skin-invert-image]]5,6-Difluoro-EPTartificial5-F, 6-FCH2CH3CH2CH2CH35,6-difluoro-N-ethyl-N-propyltryptamine
[[File:5-MeO-2,N,N-TMT.svg120pxclass=skin-invert-image]][5-MeO-2-TMT](5-meo-2-tmt)artificial2-CH3, 5-OCH3CH3CH32-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine67292-68-6
[[File:5-MeO-7-TMT 2D.svg120pxclass=skin-invert-image]][5-MeO-7-TMT](5-methoxy-7-n-n-trimethyltryptamine)artificial5-OCH3, 7-CH3CH3CH35-Methoxy-7,*N*,*N*-trimethyltryptamine61018-77-7
[[File:5-MeO-4NN-TMT_structure.png120pxclass=skin-invert-image]]5-MeO-4-TMTartificial4-CH3, 5-OCH3CH3CH35-Methoxy-4,*N*,*N*-trimethyltryptamine
[[File:4-HO-5-MeO-DMT.svg120pxclass=skin-invert-image]][4-HO-5-MeO-DMT](4-hydroxy-5-methoxydimethyltryptamine) (psilomethoxin)artificial4-OH, 5-OCH3CH3CH34-Hydroxy-5-methoxy-*N*,*N*-dimethyltryptamine2433-31-0
[[File:4-Fluoro-5-methoxy-N,N-dimethyltryptamine.svg120pxclass=skin-invert-image]][4-F-5-MeO-DMT](4-fluoro-5-methoxy-dmt)artificial4-F, 5-OCH3CH3CH34-Fluoro-5-Methoxy-*N*,*N*-dimethyltryptamine312314-18-4
[[File:7-F-5-MeO-MET_2D.svg120pxclass=skin-invert-image]][5-MeO-7-F-MET](7f-5-meo-met)artificial5-OCH3, 7-FCH3CH2CH35-Methoxy-7-Fluoro-*N*-methyl-*N*-ethyltryptamine
[[File:EMDT_structure.svg120pxclass=skin-invert-image]]EMDT (2-ethyl-5-MeO-DMT)artificial2-CH2CH3, 5-OCH3CH3CH32-(2-ethyl-5-methoxy-1H-indol-3-yl)-*N*,*N*-dimethylethanamine263744-72-5
[[File:ST-1936_structure.svg120pxclass=skin-invert-image]]ST-1936 (2-methyl-5-chloro-DMT)artificial2-CH3, 5-ClCH3CH32-(2-methyl-5-chloro-1H-indol-3-yl)-*N*,*N*-dimethylethanamine1210-81-7
[[File:O-4310_structure.svg120pxclass=skin-invert-image]]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
[[File:CP-132,484 Structure.svg120pxclass=skin-invert-image]]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
[[File:4,5-DHP-DMT.svg120pxclass=skin-invert-image]][4,5-DHP-DMT](4-5-dhp-dmt)artificial4,5-(OCH2CH2CH2)CH3CH31-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-*e*]indole135360-97-3
[[File:4,5-DHF-DMT_structure.png120pxclass=skin-invert-image]]4,5-DHF-DMT (**P-3**)artificial4,5-(CH2CH2O)CH3CH32-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
[[File:4,5-Methylbenzodioxole-DMT_structure.png120pxclass=skin-invert-image]]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
[[File:4,5-MDO-DMT.svg120pxclass=skin-invert-image]][4,5-MDO-DMT](4-5-mdo-dmt)artificial4,5-(OCH2O)CH3CH32-(2*H*,6*H*-[1,3]Dioxolo[4,5-*e*]indol-8-yl)-*N*,*N*-dimethylethan-1-amine81249-30-1
[[File:4,5-MDO-DiPT.svg120pxclass=skin-invert-image]][4,5-MDO-DiPT](4-5-mdo-dipt)artificial4,5-(OCH2O)CH(CH3)2CH(CH3)2*N*-[2-(2*H*,6*H*-[1,3]Dioxolo[4,5-*e*]indol-8-yl)ethyl]-*N*-(propan-2-yl)propan-2-amine82173-82-8
[[File:5,6-FUR-DMT structure.png120pxclass=skin-invert-image]]5,6-FUR-DMT (**P-4**)artificial5,6-(CH=CHO)CH3CH32-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine
[[File:5,6-MDO-DMT.svg120pxclass=skin-invert-image]][5,6-MDO-DMT](5-6-mdo-dmt)artificial5,6-(OCH2O)CH3CH32-(2*H*,5*H*-[1,3]Dioxolo[4,5-*f*]indol-7-yl)-*N*,*N*-dimethylethan-1-amine
[[File:5,6-MDO-MiPT.svg120pxclass=skin-invert-image]][5,6-MDO-MiPT](5-6-mdo-mipt)artificial5,6-(OCH2O)CH3CH(CH3)2*N*-[2-(2*H*,5*H*-[1,3]Dioxolo[4,5-*f*]indol-7-yl)ethyl]-*N*-methylpropan-2-amine
[[File:5,6-MDO-DiPT.svg120pxclass=skin-invert-image]][5,6-MDO-DiPT](5-6-mdo-dipt)artificial5,6-(OCH2O)CH(CH3)2CH(CH3)2*N*-[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. 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, and produce psychostimulant, entactogen, and/or psychedelic effects. The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs. In accordance with its action as a dual releasing agent of serotonin and dopamine, αET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as αMT, 5-MeO-αMT, and various others.

StructureNameChemical nameCAS #
[[File:L-Tryptophan - L-Tryptophan.svg120pxclass=skin-invert-image]]Tryptophan(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid73-22-3
[[File:5-Hydroxy-L-Tryptophan_(5-HTP).svg120pxclass=skin-invert-image]][5-Hydroxytryptophan](5-hydroxytryptophan) (5-HTP)2-amino-3-(5-hydroxy-1*H*-indol-3-yl)propanoic acid4350-09-8
[[File: AMT.svg120pxclass=skin-invert-image]]αMT (AMT; Indopan)1-(1*H*-Indol-3-yl)propan-2-amine299-26-3
[[File:4-HO-aMT Structure.svg120pxclass=skin-invert-image]][4-HO-αMT](4-ho-amt)3-(2-aminopropyl)-1*H*-indol-4-ol15066-09-8
[[File:4-Methyl-AMT.png125pxclass=skin-invert-image]][4-Methyl-αMT](4-me-amt)1-methyl-2-(4-methyl-1*H*-indol-3-yl)-ethylamine3569-29-7
[[File:5-fluoro-alpha-methyltryptamine.svg130pxclass=skin-invert-image]][5-Fluoro-αMT](5-fluoro-amt)1-(5-fluoro-1H-indol-3-yl)propan-2-amine712-08-3
[[File:5-Chloro-3-(2-aminopropyl)indole.svg125pxclass=skin-invert-image]][5-Chloro-αMT](5-chloro-amt)1-(5-Chloro-1H-indol-3-yl)propan-2-amine712-07-2
[[File:Alpha-methylserotonin.svg120pxclass=skin-invert-image]]5-HO-αMT (αMS/α-methyl-5-HT)3-(2-aminopropyl)-1*H*-indol-5-ol304-52-9
[[File:5-MeO-AMT.svg120pxclass=skin-invert-image]][5-MeO-αMT](5-meo-amt)1-(5-methoxy-1*H*-indol-3-yl)propan-2-amine1137-04-8
[[File:5-EtO-AMT.svg125pxclass=skin-invert-image]][5-Ethoxy-αMT](5-ethoxy-amt)1-(5-ethoxy-1*H*-indol-3-yl)propan-2-amine101832-83-1
[[File:5-iPrO-AMT_structure.png125pxclass=skin-invert-image]]5-Isopropoxy-αMT1-{5-[(propan-2-yl)oxy]-1*H*-indol-3-yl}propan-2-amine
[[File:5-Allyloxy-AMT.svg125pxclass=skin-invert-image]][5-Allyloxy-αMT](5-allyloxy-amt)1-{5-[(prop-2-en-1-yl)oxy]-1*H*-indol-3-yl}propan-2-amine
[[File:BW-723C86.svg120pxclass=skin-invert-image]]BW-723C861-[5-(2-Thienylmethoxy)-1*H*-indol-3-yl]-2-propanamine160521-72-2
[[File:6-fluoro-AMT.svg120pxclass=skin-invert-image]][6-Fluoro-αMT](6-fluoro-amt)1-(6-fluoro-1H-indol-3-yl)propan-2-amine712-11-8
[[File:7-Chloro-AMT.svg120pxclass=skin-invert-image]][7-Chloro-AMT](7-chloro-amt)1-(7-chloro-1H-indol-3-yl)propan-2-amine711-99-9
[[File:AL-37350A Structure.svg120pxclass=skin-invert-image]]AL-37350A (4,5-DHP-αMT)(*S*)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-*e*]indole362603-40-5
[[File:BIAP_structure.png120pxclass=skin-invert-image]]vauthors = Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RAtitle = Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptorsjournal = Bioorganic & Medicinal Chemistry Lettersvolume = 12issue = 2pages = 155–8date = January 2002pmid = 11755343doi = 10.1016/s0960-894x(01)00713-2 }}1-(3H-benzo[e]indol-1-yl)propan-2-amine
[[File:AET.svg120pxclass=skin-invert-image]]αET1-(1*H*-indol-3-yl)butan-2-amine2235-90-7
[[File:4-Methyl-AET.png120pxclass=skin-invert-image]][4-Methyl-αET](4-me-aet)1-(4-Methyl-1*H*-indol-3-yl)butan-2-amine28289-30-7
[[File:4-HO-AET 2D.svg120pxclass=skin-invert-image]][4-HO-αET](4-ho-aet)1-(4-hydroxy-1*H*-indol-3-yl)butan-2-amine28289-28-3
[[File:5-Fluoro-AET.svg120pxclass=skin-invert-image]][5-Fluoro-αET](5-fluoro-aet)1-(5-fluoro-1H-indol-3-yl)butan-2-amine1380137-98-3
[[File:5Me-AET_structure.png125pxclass=skin-invert-image]]5-Methyl-αET1-(5-methyl-1H-indol-3-yl)butan-2-amine1380148-21-9
[[File:5-MeO-AET.svg125pxclass=skin-invert-image]][5-MeO-αET](5-meo-aet)1-(5-methoxy-1H-indol-3-yl)butan-2-amine4765-10-0
[[File:7-Methyl-AET.svg130pxclass=skin-invert-image]][7-Methyl-αET](7-methyl-aet)1-(7-methyl-1*H*-indol-3-yl)butan-2-amine13712-80-6
[[File:A,N-DMT.svg125pxclass=skin-invert-image]]α,*N*-DMT (SK&F-7024, Ro 3-1715; *N*-methyl-AMT)1-(1*H*-indol-3-yl)-N-methylpropan-2-amine299-24-1
[[File:A,N,N-TMT.svg125pxclass=skin-invert-image]]N,N-Dimethyl-αMT (α,*N*,*N*-TMT)(2-(1*H*-Indol-3-yl)-1-methyl-ethyl)dimethylamine4761-32-4
[[File:N-Hydroxy-AMT.svg125pxclass=skin-invert-image]]*N*-Hydroxy-AMT (*N*-HO-AMT)*N*-[1-(1*H*-indol-3-yl)propan-2-yl]hydroxylamine63-33-2
[[File:A,N,O-TMS.svg125pxclass=skin-invert-image]]N-Methyl-5-MeO-αMT (α,*N*,*O*-TMS/α,*N*,*O*-trimethyl-5-HT)1-(5-methoxy-1*H*-indol-3-yl)propan-2-ylamine4822-13-3
[[File:Alpha,N,N,O-tetramethylserotonin.svg120pxclass=skin-invert-image]]*N*,*N*-Dimethyl-5-MeO-αMT (5-MeO-α,*N*,*N*-TMT)(2-(5-methoxy-1*H*-Indol-3-yl)-1-methyl-ethyl)dimethylamine101831-90-7
[[File:Alpha-propyl-tryptamine.svg125pxclass=skin-invert-image]]α-Propyltryptamine (APT; αPT; α-PT)1-(1*H*-indol-3-yl)pentan-2-amine
[[File:Indolylpropylaminopentane.svg125pxclass=skin-invert-image]]Indolylpropylaminopentane (IPAP; α,*N*-DPT)1-(1*H*-indol-3-yl)-*N*-propylpentan-2-amine
[[File:AMDIPT_structure.png125pxclass=skin-invert-image]]α-Methyl-DiPT(2-(1*H*-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
[[File:MPMI_structure.svg130pxclass=skin-invert-image]]MPMI3-[(1-methylpyrrolidin-2-yl)methyl]-1*H*-indole143321-54-4
[[File:4-HO-MPMI 2D.svg130pxclass=skin-invert-image]]Lucigenol (4-HO-MPMI)(*R*)-3-(*N*-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole250672-65-2
[[File:5-MeO-N-Me-TMT.svg130pxclass=skin-invert-image]][5-MeO-MPMI](5-meo-mpmi) (CP-108509)5-Methoxy-3-{[(2*R*)-1-methylpyrrolidin-2-yl]methyl}-1*H*-indole143321-57-7
[[File:5-Fluoro-MPMI 2D.svg130pxclass=skin-invert-image]][5F-MPMI](5f-mpmi)(*R*)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1*H*-indole
[[File:5Br-MPMI_structure.png130pxclass=skin-invert-image]]5-Br-MPMI5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1*H*-indole143322-57-0
[[File:Eletriptan skeletal.svg130pxclass=skin-invert-image]]Eletriptan3-{[(2*R*)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1*H*-indole143322-58-1
[[File:Z5247692566_structure.png130pxclass=skin-invert-image]]vauthors = Callaway Etitle=AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery?journal=Nature Newsdate=18 January 2024volume=626issue=7997pages=14–15doi=10.1038/d41586-024-00130-8pmid=38238624bibcode=2024Natur.626...14Cs2cid=267040499 }}4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine
[[File:Β-Keto-N-methyl-αMT.svg130pxclass=skin-invert-image]]vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RBtitle = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomesjournal = Psychopharmacology (Berl)volume = 236issue = 3pages = 915–924date = March 2019pmid = 30341459pmc = 6475490doi = 10.1007/s00213-018-5063-9url = }}1-(1*H*-indol-3-yl)-2-(methylamino)propan-1-one
[[File:BK-5F-NM-AMT structure.png130pxclass=skin-invert-image]]title=1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-onewebsite=PubChemurl=https://pubchem.ncbi.nlm.nih.gov/compound/162765676access-date=11 November 2024}}1-(5-fluoro-1*H*-indol-3-yl)-2-(methylamino)propan-1-one
[[File:BK-5Cl-NM-AMT.svg130pxclass=skin-invert-image]]title=1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-onewebsite=PubChemurl=https://pubchem.ncbi.nlm.nih.gov/compound/162765502access-date=11 November 2024}}1-(5-chloro-1*H*-indol-3-yl)-2-(methylamino)propan-1-one
[[File:BK-5Br-NM-AMT.svg130pxclass=skin-invert-image]]title=1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-onewebsite=PubChemurl=https://pubchem.ncbi.nlm.nih.gov/compound/162765532access-date=11 November 2024}}1-(5-bromo-1*H*-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:

  • β-Carbolines such as harmala alkaloids like harmaline
  • Ibogalogs (hexahydroazepinoindoles) such as ibogainalog, tabernanthalog, PNU-22394, and PHA-57378
  • Iboga alkaloids like ibogaine, noribogaine, ibogamine, and tabernanthine
  • Ergolines and lysergamides such as lysergic acid diethylamide (LSD) and ergot alkaloids like ergine (lysergic acid amide; LSA)
  • Partial ergolines and lysergamides like RU-27849, FHATHBIN, NDTDI, and CT-5252
  • Mitragyna alkaloids such as mitragynine
  • Yohimbans such as Rauvolfia and Corynanthe alkaloids like yohimbine and rauwolscine
  • Pertines (phenylpiperazinylethylindoles) like alpertine, milipertine, oxypertine, and solypertine
  • Imidazolylindoles like AGH-107, AGH-192, and AH-494
  • Morpholinylethylindoles like mor-T and 5-MeO-mor-T
  • Piperidinylethylindoles like pip-T and 5-MeO-pip-T
  • Pyrrolidinylethylindoles like pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, and L-760790
  • Pyrrolidinylmethylindoles like MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-135807, eletriptan, and MSP-2020
  • Tetrahydropyridinylindoles like RS134-49 (4-Me-THPI), RU-28253 (5-MeO-THPI), and NEtPhOH-THPI
  • Tetrahydrocarbazolamines like ciclindole, flucindole, frovatriptan, LY-344864, and ramatroban
  • Tetrahydropyrroloquinolines like bufothionine, O-methylnordehydrobufotenine, and dehydrobufotenine
  • Others like 5-MeO-IsoqT, barettin, cyclic 3-hydroxymelatonin, and metralindole

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

  • Piperidinylindoles like SN-22, BRL-54443, naratriptan, LY-334370, and sertindole
  • Tetrahydropyridinylindoles like RU-24969, EMD-386088, and LY-367,265
  • Tetrahydropyridinylindazoles like VU6067416
  • Tetrahydropyridinylpyrrolopyridines like (R)-69, (R)-70, CP-93129, and CP-94253
  • Pyridopyrroloquinoxalines (tetracyclic γ-carbolines) like lumateperone, IHCH-7113, IHCH-7086, and ITI-1549

Overview table

References

References

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