Substituted tryptamine

The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN₁=RN₂=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. ^[1]

The tryptamine structure, in particular its indole ring, may be part of the structure of some more complex compounds, for example cyclized tryptamines like LSD, ibogaine, harmaline, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Alexander Shulgin and Ann Shulgin in 1997 under the title TiHKAL (Tryptamines I Have Known and Loved). ^[2]

Use and effects

The doses, potencies, durations, and effects of psychedelic tryptamines have been reviewed by Alexander Shulgin and other authors. ^{[3] [4] [5] [6] [2] [7] [8] [9] [10] [11]}

Ring-unsubstituted tryptamines

Oral doses and durations of ring-unsubstituted tryptamines

Compound	Chemical name	Dose	Duration
Tryptamine (T)	Tryptamine	>100 mga	–
NMT	N-Methyltryptamine	Unknownb	–
NET	N-Ethyltryptamine	Unknown	Unknown
NiPT	N-Isopropyltryptamine	Unknown	Unknown
NsBT	N-sec-Butyltryptamine	25–75 mg	"Short"
NtBT	N-tert-Butyltryptamine	5–20 mg	Unknown
NAT	N-Amyltryptamine	>100 mg	–
NHT	N-Hexyltryptamine	>100 mg	–
DMT	N,N-Dimethyltryptamine	>350 mgc	–
DET	N,N-Diethyltryptamine	50–150 mg	2–4 hours
DPT	N,N-Dipropyltryptamine	100–250 mg	2–4 hours
DiPT	N,N-Diisopropyltryptamine	25–100 mg (15–150 mg+)	6–8 hours
DALT	N,N-Diallyltryptamine	60–80 mg	<3 hours
DBT	N,N-Dibutyltryptamine	≥100 mg	Unknown
DAT	N,N-Diamyltryptamine	Unknown	Unknown
DHT	N,N-Dihexyltryptamine	>100 mg	–
MET	N-Methyl-N-ethyltryptamine	80–100 mg	Unknown
MPT	N-Methyl-N-propyltryptamine	>50 mg	Unknown
MiPT	N-Methyl-N-isopropyltryptamine	10–25 mg	3–4 hours
MALT	N-Methyl-N-allyltryptamine	Unknown	Unknown
MBT	N-Methyl-N-butyltryptamine	250–400 mg	4–6 hours
MsBT	N-Methyl-N-sec-butyltryptamine	250–400 mg	Unknown
EPT	N-Ethyl-N-propyltryptamine	Unknown	Unknown
EiPT	N-Ethyl-N-isopropyltryptamine	24–40 mg	4–6 hours
PiPT	N-Propyl-N-isopropyltryptamine	Unknown	Unknown
Pyr-T	N,N-Tetramethylenetryptamine	Unknown	Unknown
Footnotes:a = Tryptamine is not orally active, but is active intravenously at a dose of 250 mg with a very short duration. b = NMT is not orally active, but is said to be active smoked at a dose of 50 to 120 mg with a duration of seconds to minutes. Also reportedly orally active with an MAOI Tooltip monoamine oxidase inhibitor. c = DMT is active parenterally at doses of 50 to 100 mg (2–100 mg) smoked, intramuscularly, or subcutaneously and at doses of 4 to 30 mg intravenously (bolus), with a duration of <1 hour or 5–20 minutes. For continuous intravenous infusion, the dose is 0.6 to 2.4 mg/minute. Also orally active with an MAOI (as in ayahuasca or pharmahuasca), with a typical dose of 50 mg (range 20–120 mg) and a duration of 4 to 6 hours. Refs: [3] [4] [2] [7] [8] [9] [11] Individual: [12] [13] [14] [15] [16] [17] [18] [19] [20] [21] [22]

4-Hydroxytryptamines

Oral doses and durations of 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	Unknown	Unknown
4-PrO-DMT	4-Propionyloxy-N,N-dimethyltryptamine	Unknown	Unknown
4-HO-DET (ethocin)	4-Hydroxy-N,N-diethyltryptamine	10–25 mg	4–6 hours
Ethocybin (4-PO-DET)	4-Phosphoryloxy-N,N-diethyltryptamine	15–30 mg	4–6 hours
4-HO-DPT (deprocin)	4-Hydroxy-N,N-dipropyltryptamine	>20 mg	5–8 hours
4-HO-DiPT (iprocin)	4-Hydroxy-N,N-diisopropyltryptamine	12–20 mg (3–30 mg+)	2–3 hours
4-AcO-DiPT (ipracetin)	4-Acetoxy-N,N-diisopropyltryptamine	6–10 mg	Unknown
Luvesilocin (4-GO-DiPT)	4-Glutaryloxy-N,N-diisopropyltryptamine	Unknownb	Unknownb
4-HO-DALT (daltocin)	4-Hydroxy-N,N-diallyltryptamine	Unknown	Unknown
4-HO-DBT	4-Hydroxy-N,N-dibutyltryptamine	>20 mg	Unknown
4-HO-DiBT	4-Hydroxy-N,N-diisobutyltryptamine	>20 mg	Unknown
4-HO-DtBT	4-HydroxyN,N-di-tert-butyltryptamine	Unknown	Unknown
4-HO-MET (metocin)	4-Hydroxy-N-methyl-N-ethyltryptamine	10–20 mg (2–45 mg+)	4–6 hours
4-HO-MPT (meprocin)	4-Hydroxy-N-methyl-N-propyltryptamine	8–30 mg	Unknown
4-HO-MiPT (miprocin)	4-Hydroxy-N-methyl-N-isopropyltryptamine	12–25 mg (6–30 mg)	4–6 hours
4-HO-MALT (maltocin)	4-Hydorxy-N-methyl-N-allyltryptamine	Unknown	Unknown
4-HO-MtBT	4-Hydroxy-N-methyl-N-tert-butyltryptamine	>15 mg	Unknown
4-HO-EPT (eprocin)	4-Hydroxy-N-ethyl-N-propyltryptamine	Unknown	Unknown
4-HO-EiPT	4-Hydroxy-N-ethyl-N-isopropyltryptamine	Unknown	Unknown
4-HO-PiPT (piprocin)	4-Hydroxy-N-propyl-N-isopropyltryptamine	Unknown	Unknown
4-HO-TMT	4-Hydroxy-N,N,N-trimethyltryptamine	Unknown	Unknown
Aeruginascin (4-PO-TMT)	4-Phosphoryloxy-N,N,N-trimethyltryptamine	Unknown	Unknown
4-HO-pyr-T	4-Hydroxy-N,N-tetramethylenetryptamine	>20 mg	Unknown
Footnotes:a = Baeocystin has conflicting reports, some say that it's active and some say that it's inactive. b = Luvesilocin is known to be active subcutaneously at doses of 5 to 40 mg with an average duration of 3.6 hours. Refs: [3] [4] [2] [7] [8] [9] [11] Individual: [14] [15] [23] [24]

5-Hydroxytryptamines

Oral doses and durations of 5-hydroxytryptamines

Compound	Chemical name	Dose	Duration
Serotonin (5-HT, 5-HO-T)	5-Hydroxytryptamine	>100 mga	–
N-Methylserotonin (norbufotenin; 5-HO-NMT)	5-Hydroxy-N-methyltryptamine	Unknown	Unknown
Bufotenin (5-HO-DMT)	5-Hydroxy-N,N-dimethyltryptamine	>100 mgb	–
O-Acetylbufotenin (5-AcO-DMT)	5-Acetoxy-N,N-dimethyltryptamine	Unknown	Unknown
O-Pivalylbufotenin (5-t-BuCO-DMT)	5-Pivaloxy-N,N-dimethyltryptamine	Unknown	Unknown
5-HO-DET	5-Hydroxy-N,N-diethyltryptamine	Unknown	Unknown
5-HO-DPT (DiPS, NDPS)	5-Hydroxy-N,N-dipropyltryptamine	Unknown	Unknown
5-HO-DiPT	5-Hydroxy-N,N-diisopropyltryptamine	Unknown	Unknown
Footnotes:a = Serotonin does not cross the blood–brain barrier and is not psychoactive. b = Bufotenin is not orally active, but is active at intravenously at doses of 8 to 16 mg with a duration of 1 to 2 hours and is active via insufflation and other parenteral routes. Refs: [3] [4] [2] [11] Individual: [25] [26] [27] [28]

5-Methoxytryptamines

Oral doses and durations of 5-methoxytryptamines

Compound	Chemical name	Dose	Duration
5-MT (5-MeO-T)	5-Methoxytryptamine	Unknown	Unknown
5-MeO-NMT	5-Methoxy-N-methyltryptamine	Unknown	Unknown
5-MeO-NET	5-Methoxy-N-ethyltryptamine	Unknown	Unknown
5-MeO-NiPT	5-Methoxy-N-isopropyltryptamine	Unknown	Unknown
5-MeO-DMT (mebufotenin)	5-Methoxy-N,N-dimethyltryptamine	>35 mga	–
5-MeO-DET	5-Methoxy-N,N-diethyltryptamine	1–3 mg	3–4 hours
5-MeO-DPT	5-Methoxy-N,N-dipropyltryptamine	6–10 mg	2–4 hours
5-MeO-DiPT	5-Methoxy-N,N-diisopropyltryptamine	6–12 mg	4–8 hours
5-MeO-DALT	5-Methoxy-N,N-diallyltryptamine	12–25 mg	2–4 hours
5-MeO-DBT	5-Methoxy-N,N-dibutyltryptamine	Unknown	Unknown
5-MeO-DsBT	5-Methoxy-N,N-di-sec-butyltryptamine	Unknown	Unknown
5-MeO-MET	5-Methoxy-N-methyl-N-ethyltryptamine	Unknown	Unknown
5-MeO-MPT	5-Methoxy-N-methyl-N-propyltryptamine	Unknown	Unknown
5-MeO-MiPT	5-Methoxy-N-methyl-N-isopropyltryptamine	4–6 mg (0.5–20 mg+)	4–6 hours
5-MeO-MALT	5-Methoxy-N-methyl-N-allyltryptamine	Unknown	Unknown
5-MeO-EPT	5-Methoxy-N-ethyl-N-propyltryptamine	Unknown	Unknown
5-MeO-EiPT	5-Methoxy-N-ethyl-N-isopropyltryptamine	Unknown	Unknown
5-MeO-PiPT	5-Methoxy-N-propyl-N-isopropyltryptamine	Unknown	Unknown
ASR-3001 (5-MeO-iPALT)	5-Methoxy-N-isopropyl-N-allyltryptamine	8–14 mg	1.5–2.5 hours
5-MeO-pyr-T	5-Methoxy-N,N-tetramethylenetryptamine	0.5–2 mg	Several hours
Melatonin (5-MeO-NAcT)	5-Methoxy-N-acetyltryptamine	1–10 mgb	A few hours
Footnotes:a = 5-MeO-DMT is not orally active, but is active at a dose of 2 to 20 mg smoked or 2 to 3 mg intravenously, with a duration of 5 to 20 minutes. Also orally active with an MAOI Tooltip monoamine oxidase inhibitor at doses of 10 to 25 mg. b = Melatonin is not a psychedelic but a hypnotic and is non-hallucinogenic at doses of up to 1,200 mg. Refs: [3] [4] [2] [7] [8] [9] [11] Individual: [15] [18]

α-Alkyltryptamines

Oral doses and durations of α-alkyltryptamines

Compound	Chemical name	Dose	Duration
AMT (α-methyl-T; Indopan)a	α-Methyltryptamine	15–40 mg	12–16 hours
AET (α-ethyl-T; etryptamine; Monase)b	α-Ethyltryptamine	100–160 mg	6–8 hours
α,N-DMT (N-methyl-AMT)c	α-Methyl-N-methyltryptamine	50–100 mg	6–8 hours
α,N,N-TMT (N,N-dimethyl-AMT)	α,N,N-Trimethyltryptamine	Unknownd	Unknown
2,α-DMT (2-methyl-AMT)	2-Methyl-α-methyltryptamine	300–500 mg	7–10 hours
4-HO-AMT (MP-14)	4-Hydroxy-α-methyltryptamine	15–20 mg+	Unknown
4-Methyl-AMT (MP-809)	4-Methyl-α-methyltryptamine	20–60 mg+	Unknown
5-Fluoro-AMT (PAL-212, PAL-544)	5-Fluoro-α-methyltryptamine	25 mg+	>9 hours
5-Chloro-AMT (PAL-542)	5-Chloro-α-methyltryptamine	Unknown	Unknown
5-Fluoro-AET (PAL-545)	5-Fluoro-α-ethyltryptamine	Unknown	Unknown
5-Chloro-AET (PAL-526)	5-Chloro-α-ethyltryptamine	Unknown	Unknown
6-Fluoro-AMT	6-Fluoro-α-methyltryptamine	25–75 mg	"Long"
α-Methylserotonin (AMS; 5-HO-AMT)	α-Methyl-5-hydroxytryptamine	Unknown	Unknown
α,O-DMS (5-MeO-AMT)	α-Methyl-5-methoxytryptamine	2.5–5 mg (0.5–15 mg)	12–18 hours
α,N,O-TMS (5-MeO-N-methyl-AMT)	α-Methyl-5-methoxy-N-methyltryptamine	10–20 mg	6–8 hours
α,N,N,O-TeMS (5-MeO-N,N-dimethyl-AMT)	5-Methoxy-α,N,N-trimethyltryptamine	Unknown	Unknown
5-MeO-AET	α-Ethyl-5-methoxytryptamine	~70 mg	Several hours
Bk-NM-AMT (β-keto-N-methyl-AMT)e	α-Methyl-β-keto-N-methyltryptamine	Unknown	Unknown
Footnotes:a = AMT is a not only a psychedelic but is also a stimulant and entactogen. b = AET is an entactogen and stimulant and is not a psychedelic. c = α,N-DMT is a stimulant and is not a psychedelic or entactogen. d = α,N,N-TMT has been reported to be an active psychedelic orally but to be much less potent than AMT. e = Bk-NM-AMT is expected to be an entactogen and stimulant but not a psychedelic. Refs: [3] [4] [2] [7] [8] [11] Individual: [29] [30]

Other tryptamines

Oral doses and durations of other tryptamines

Compound	Chemical name	Dose	Duration
2-Methyl-DMT	2-Methyl-N,N-dimethyltryptamine	50–100 mg	4–6 hours
2-Methyl-DET	2-Methyl-N,N-diethyltryptamine	80–120 mg	6–8 hours
4-MeO-DMT	4-Methoxy-N,N-dimethyltryptamine	Unknown	Unknown
4-MeO-DET	4-Methoxy-N,N-diethyltryptamine	>30 mg	Unknown
4-MeO-DiPT	4-Methoxy-N,N-diisopropyltryptamine	Unknown	Unknown
4-MeO-MiPT	4-Methoxy-N-methyl-N-isopropyltryptamines	20–30 mg	4–6 hours
4,5-MDO-DMT	4,5-Methylenedioxy-N,N-dimethyltryptamine	Unknown	Unknown
4,5-MDO-DiPT	4,5-Methylenedioxy-N,N-diisopropyltryptamine	>25 mg	Unknown
5-Fluoro-DMT	5-Fluoro-N,N-dimethyltryptamine	Unknown	Unknown
5-Chloro-DMT	5-Chloro-N,N-dimethyltryptamine	Unknown	Unknown
5-Bromo-DMT	5-Bromo-N,N-dimethyltryptamine	Unknowna	Unknown
Bretisilocin (5-fluoro-MET)	5-Fluoro-N-methyl-N-ethyltryptamine	Unknownb	Unknownb
5-MeO-2-TMT	5-Methoxy-2-methyl-N,N-dimethyltryptamine	75–150 mg	5–10 hours
5-MeS-DMT	5-Methylthio-N,N-dimethyltryptamine	Unknownc	Unknownc
5,6-MeO-MiPT	5,6-Dimethoxy-N-methyl-N-isopropyltryptamine	>75 mg	Unknown
5,6-MDO-DMT	5,6-Methylenedioxy-N,N-dimethyltryptamine	>5 mg	Unknown
5,6-MDO-DiPT	5,6-Methylenedioxy-N,N-diisopropyltryptamine	Unknown	Unknown
5,6-MDO-MiPT	5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine	>50–60 mg	Unknown
6-Fluoro-DMT	6-Fluoro-N,N-dimethyltryptamine	Unknown	Unknown
6-Fluoro-DET	6-Fluoro-N,N-diethyltryptamine	>80 mg	Unknown
6-HO-DMT	6-Hydroxy-N,N-dimethyltryptamine	>80 mg	Unknown
6-MeO-DiPT	6-Methoxy-N,N-diisopropyltryptamine	>50 mg	Unknown
6-MeO-MiPT	6-Methoxy-N-methyl-N-isopropyltryptamine	>50 mg	Unknown
7-MeO-DiPT	7-Methoxy-N,N-diisopropyltryptamine	>70 mg	Unknown
7-MeO-MiPT	7-Methoxy-N-methyl-N-isopropyltryptamine	>70 mg	Unknown
Footnotes:a 5-Bromo-DMT is active via smoking at a dose of 20 to 50 mg. b = Bretisilocin is active intravenously with a dose range of 10 to 20 mg and a duration of 60 to 90 minutes. c = 5-MeS-DMT's oral dose and duration are unknown, but smoked the dose is 15 to 30 mg and the duration is 10 to 30 minutes or <1 hour. Refs: [3] [4] [2] [9] [11] Individual: [31] [32]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

List of substituted tryptamines

Structure	Name	Origin	Ring sub.	RN1	RN2	Chemical name	CAS #
	Tryptamine (T)	Animals, plants, fungi	H	H	H	3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine	61-54-1
	NMT	Plants	H	H	CH3	N-methyltryptamine	61-49-4
	2-HO-NMT	Plants	2-OH	H	CH3	2-hydroxy-N-methyltryptamine	106987-89-7
	5-MeO-NMT	Plants	5-OCH3	H	CH3	5-methoxy-N-methyltryptamine	2009-03-2
	Serotonin (5-HT)	Animals, plants	5-OH	H	H	5-hydroxytryptamine	50-67-9
	N-Methylserotonin (NMS; norbufotenin; 5-HO-NMT)	Plants	5-OH	H	CH3	5-hydroxy-N-methyltryptamine	1134-01-6
	Bufotenin (5-HO-DMT)	Animals, plants, fungi	5-OH	CH3	CH3	5-hydroxy-N,N-dimethyltryptamine	487-93-4
	Bufotenidine (5-HTQ)	Amphibians	5-O−	(CH3)3		3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate	487-91-2
	Bufoviridine (5-SO-DMT)	Amphibians	5-SO	CH3	CH3	5-sulfooxy-N,N-dimethyltryptamine	16369-08-7
	Melatonin (5-MeO-NAcT)	Animals, plants, microbes	5-OCH3	H	O=C-CH3	5-methoxy-N-acetyltryptamine	73-31-4
	N-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT)	Animals	5-OH	H	O=C-CH3	5-hydroxy-N-acetyltryptamine	1210-83-9
	6-Hydroxymelatonin	Animals	5-OCH3, 6-OH	H	O=C-CH3	N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide	2208-41-5
	4-Hydroxytryptamine (4-HT)	Fungi	4-OH	H	H	4-hydroxytryptamine	570-14-9
	4-HO-NMT	Fungi	4-OH	H	CH3	4-hydroxy-N-methyltryptamine	28363-70-4
	Psilocin (4-HO-DMT)	Fungi	4-OH	CH3	CH3	4-hydroxy-N,N-dimethyltryptamine	520-53-6
	4-HO-TMT	Fungi	4-OH	CH3	CH3	4-hydroxy-N,N,N-trimethyltryptammonium	262285-41-6
	Norbaeocystin (4-PO-T)	Fungi	4-OPO3H2	H	H	4-phosphoryloxy-tryptamine	21420-59-7
	Baeocystin (4-PO-NMT)	Fungi	4-OPO3H2	H	CH3	4-phosphoryloxy-N-methyl-tryptamine	21420-58-6
	Psilocybin (4-PO-DMT)	Fungi	4-OPO3H2	CH3	CH3	4-phosphoryloxy-N,N-dimethyltryptamine	520-52-5
	Aeruginascin (4-PO-TMT)	Fungi	4-OPO3H2	(CH3)3		[3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate	114264-95-8
	DMT	Animals, plants	H	CH3	CH3	N,N-dimethyltryptamine	61-50-7
	Lespedamine (1-MeO-DMT)	Plants	1-OCH3	CH3	CH3	1-methoxy-N,N-dimethyltryptamine	4335-93-7
	5-MeO-DMT (mebufotenin)	Animals, plants	5-OCH3	CH3	CH3	5-methoxy-N,N-dimethyltryptamine	1019-45-0
	5-Bromo-DMT	Marine sponges, invertebrates	5-Br	CH3	CH3	5-bromo-N,N-dimethyltryptamine	17274-65-6
	6-Bromotryptamine	Marine invertebrates	6-Br	H	H	6-bromotryptamine	96624-18-9
	5,6-Dibromotryptamine	Marine invertebrates	5,6-Br	H	H	5,6-dibromotryptamine
	5,6-Dibromo-NMT	Marine invertebrates	5,6-Br	H	CH3	5,6-dibromo-N-methyltryptamine
	5,6-Dibromo-DMT	Marine sponges, invertebrates	5,6-Br	CH3	CH3	5,6-dibromo-N,N-dimethyltryptamine	72853-80-6
	Desformylflustrabromine (dFBr)	Marine invertebrates	2-(α,α-dimethylallyl), 6-Br	H	CH3	2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine	474657-72-2
	Convolutindole A	Marine invertebrates	2,4,6-Br, 1,7-OCH3	CH3	CH3	1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine	443356-86-3
	Acetryptine (5-AT)	artificial	5-COCH3	H	H	5-Acetyltryptamine	3551-18-6
	5-BT	artificial	5-OCH2C6H5	H	H	5-Benzyloxytryptamine	20776-45-8
	5-CT	artificial	5-CONH2	H	H	5-Carboxamidotryptamine	74885-09-9
	5-NOT	artificial	5-O(CH2)8CH3	H	H	5-Nonyloxytryptamine	157798-12-4
	2-Methyl-5-hydroxytryptamine	artificial	2-CH3, 5-OH	H	H	3-(2-aminoethyl)-2-methyl-1H-indol-5-ol	78263-90-8
	NET	artificial	H	H	CH2CH3	N-ethyltryptamine	61-53-0
	NiPT	artificial	H	H	CH(CH3)2	N-isopropyltryptamine	14121-10-9
	NcPT	artificial	H	H	C3H5	N-cyclopropyltryptamine
	NsBT	artificial	H	H	CH(CH3)CH2CH3	N-sec-butyltryptamine
	NtBT	artificial	H	H	C(CH3)3	N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine	1344092-44-9
	N-Benzyltryptamine (NBnT)	artificial	H	H	CH2C6H5	N-benzyltryptamine	15741-79-4
	4-HO-NBnT	artificial	4-OH	H	CH2C6H5	4-hydroxy-N-benzyltryptamine
	5-MeO-NBnT	artificial	5-OCH3	H	CH2C6H5	5-methoxy-N-benzyltryptamine	25100-31-6
	5-MeO-T-NBOMe	artificial	5-OCH3	H	CH2C6H4(o-OCH3)	5-methoxy-N-(ortho-methoxybenzyl)tryptamine	1335331-37-7
	5-MT-NB3OMe [33]	artificial	5-OCH3	H	CH2C6H4(m-OCH3)	5-methoxy-N-(meta-methoxybenzyl)tryptamine	1648553-42-7
	5-MeO-NBpBrT	artificial	5-OCH3	H	CH2C6H4(p-Br)	N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine	155639-13-7
	5-MeO-34MPEMT [34]	artificial	5-OCH3	CH3	CH2CH2C6H3(p,m-OCH3)	N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
	Idalopirdine	artificial	6-F	H	CH2C6H4(m-OCH2CF2CF2H)	2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine	467459-31-0
	Z2876442907 [35]	artificial	4-CH3	H	CH2(C3HNS)-COOCH2CH3	ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate
	Cis-2',5'-dimethyl-4-HO-azt-T [36]	artificial	4-OH	cis-(CHCH3)CH2(CHCH3)		3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol
	Pyr-T	artificial	H	(CH2)4		3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole	14008-96-9
	4-HO-pyr-T	artificial	4-OH	(CH2)4		3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol	63097-26-7
	Cis-2',5'-dimethyl-4-HO-pyr-T [36]	artificial	4-OH	cis-(CHCH3)CH2CH2(CHCH3)		3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol
	5-MeO-pyr-T	artificial	5-OCH3	(CH2)4		5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole	3949-14-2
	4-F-5-MeO-pyr-T	artificial	4-F-5-OCH3	(CH2)4		4-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole	344790-93-8
	Indolylethylfentanyl	artificial	H	(CH2)5-4-N(COCH2CH3)C6H5		N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide	58399-46-5
	MET	artificial	H	CH3	CH2CH3	N-Methyl-N-ethyltryptamine	5599-69-9
	MPT	artificial	H	CH3	CH2CH2CH3	N-Methyl-N-propyltryptamine	850032-72-3
	MiPT	artificial	H	CH3	CH(CH3)2	N-Methyl-N-isopropyltryptamine	96096-52-5
	McPT	artificial	H	CH3	C3H5	N-Methyl-N-cyclopropyltryptamine	1373918-63-8
	EcPT	artificial	H	CH2CH3	C3H5	N-ethyl-N-cyclopropyltryptamine
	PcPT	artificial	H	CH2CH2CH3	C3H5	N-propyl-N-cyclopropyltryptamine
	iPcPT	artificial	H	CH(CH3)2	C3H5	N-isopropyl-N-cyclopropyltryptamine
	DcPT	artificial	H	C3H5	C3H5	N,N-dicyclopropyltryptamine	1373918-62-7
	MBT	artificial	H	CH3	(CH2)3CH3	N-Methyl-N-butyltryptamine	848130-12-1
	MsBT	artificial	H	CH3	CH(CH3)CH2CH3	N-Methyl-N-sec-butyltryptamine
	MiBT	artificial	H	CH3	CH2CH(CH3)2	N-Methyl-N-iso-butyltryptamine
	McPMT	artificial	H	CH3	CH2C3H5	N-Methyl-N-(cyclopropylmethyl)tryptamine
	DET	artificial	H	CH2CH3	CH2CH3	N,N-diethyltryptamine	61-51-8
	EPT	artificial	H	CH2CH3	CH2CH2CH3	N-Ethyl-N-propyltryptamine	850032-68-7
	EiPT	artificial	H	CH2CH3	CH(CH3)2	N-Ethyl-N-isopropyltryptamine	848130-11-0
	DPT	artificial	H	CH2CH2CH3	CH2CH2CH3	N,N-dipropyltryptamine	61-52-9
	PiPT	artificial	H	CH2CH2CH3	CH(CH3)2	N-Propyl-N-isopropyltryptamine	1354632-00-0
	DiPT	artificial	H	CH(CH3)2	CH(CH3)2	N,N-diisopropyltryptamine	14780-24-6
	EBT	artificial	H	CH2CH3	(CH2)3CH3	N-ethyl-N-butyltryptamine
	PBT	artificial	H	CH2CH2CH3	(CH2)3CH3	N-propyl-N-butyltryptamine
	iPsBT	artificial	H	CH(CH3)2	CH(CH3)CH2CH3	N-isopropyl-N-sec-butyltryptamine
	DBT	artificial	H	(CH2)3CH3	(CH2)3CH3	N,N-dibutyltryptamine	15741-77-2
	DiBT	artificial	H	CH2CH(CH3)2	CH2CH(CH3)2	N,N-diisobutyltryptamine	63938-64-7
	DsBT	artificial	H	CH(CH3)CH2CH3	CH(CH3)CH2CH3	N,N-disecbutyltryptamine
	MALT	artificial	H	CH3	H2C=CH-CH2	N-methyl-N-allyltryptamine	1366416-29-6
	DALT	artificial	H	H2C=CH-CH2	H2C=CH-CH2	N,N-diallyltryptamine	60676-77-9
	iPALT (ALiPT)	artificial	H	H2C=CH-CH2	CH(CH3)2	N-allyl-N-isopropyltryptamine
	2-Methyl-DMT	artificial	2-CH3	CH3	CH3	(2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine	1080-95-1
	2-Methyl-DET	artificial	2-CH3	CH2CH3	CH2CH3	N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine	26628-88-6
	4-Amino-DMT [37]	artificial	4-NH2	CH3	CH3	4-amino-N,N-dimethyltryptamine	60331-61-5
	4-Methyl-DMT	artificial	4-CH3	CH3	CH3	4,N,N-trimethyltryptamine	28289-23-8
	4-MeO-DMT	artificial	4-OCH3	CH3	CH3	4-methoxy-N,N-dimethyltryptamine	3965-97-7
	4-MeO-MiPT	artificial	4-OCH3	CH3	CH(CH3)2	4-methoxy-N-methyl-N-isopropyltryptamine	96096-53-6
	4-MeO-DiPT	artificial	4-OCH3	CH(CH3)2	CH(CH3)2	4-methoxy-N,N-diisopropyltryptamine
	4-AcO-DMT	artificial	4-OCOCH3	CH3	CH3	4-acetoxy-N,N-dimethyltryptamine	92292-84-7
	4-PrO-DMT	artificial	4-OCOCH2CH3	CH3	CH3	4-propionyloxy-N,N-dimethyltryptamine	1373882-11-1
	4-GO-DMT (RE109; FT-109)	artificial	4-OCO(CH2)3COOH	CH3	CH3	4-glutaryloxy-N,N-dimethyltryptamine
	4-HO-MET	artificial	4-OH	CH3	CH2CH3	4-hydroxy-N-methyl-N-ethyltryptamine	77872-41-4
	4-AcO-MET	artificial	4-OCOCH3	CH3	CH2CH3	4-acetoxy-N-methyl-N-ethyltryptamine	1445751-40-5
	4-PO-MET	artificial	4-OPO3H2	CH3	CH2CH3	4-phosphoryloxy-N-methyl-N-ethyltryptamine
	4-HO-DET	artificial	4-OH	CH2CH3	CH2CH3	4-hydroxy-N,N-diethyltryptamine	22204-89-3
	4-AcO-DET	artificial	4-OCOCH3	CH2CH3	CH2CH3	4-acetoxy-N,N-diethyltryptamine	1135424-15-5
	4-PO-DET	artificial	4-OPO3H2	CH2CH3	CH2CH3	4-phosphoryloxy-N,N-diethyltryptamine	60480-02-6
	4-HO-EPT	artificial	4-OH	CH2CH3	CH2CH2CH3	4-hydroxy-N-ethyl-N-propyltryptamine	2595431-59-5
	4-PO-EPT	artificial	4-OPO3H2	CH2CH3	CH2CH2CH3	4-phosphoryloxy-N-ethyl-N-propyltryptamine
	4-AcO-EiPT	artificial	4-OCOCH3	CH2CH3	CH(CH3)2	4-acetoxy-N-ethyl-N-isopropyltryptamine
	4-HO-MPT	artificial	4-OH	CH3	CH2CH2CH3	4-hydroxy-N-methyl-N-propyltryptamine	763035-03-6
	4-HO-MiPT	artificial	4-OH	CH(CH3)2	CH3	4-hydroxy-N-isopropyl-N-methyltryptamine	77872-43-6
	4-AcO-MiPT	artificial	4-OCOCH3	CH3	CH(CH3)2	4-acetoxy-N-methyl-N-isopropyltryptamine	1024612-25-6
	4-HO-MALT [38]	artificial	4-OH	CH3	H2C=CH-CH2	4-hydroxy-N-Methyl-N-allyltryptamine
	4-AcO-MALT [39]	artificial	4-OCOCH3	CH3	H2C=CH-CH2	4-acetoxy-N-Methyl-N-allyltryptamine
	4-HO-NALT [40]	artificial	4-OH	H	H2C=CH-CH2	4-hydroxy-N-allyltryptamine
	4-HO-MsBT	artificial	4-OH	CH(CH3)CH2CH3	CH3	4-hydroxy-N-sec-butyl-N-methyltryptamine
	4-HO-EiBT	artificial [41]	4-OH	CH2CH(CH3)2	CH2CH3	4-hydroxy-N-iso-butyl-N-ethyltryptamine
	4-HO-McPT	artificial	4-OH	C3H5	CH3	4-hydroxy-N-cyclopropyl-N-methyltryptamine	2883663-05-4
	4-HO-McPeT	artificial	4-OH	C5H9	CH3	4-hydroxy-N-cyclopentyl-N-methyltryptamine	77872-48-1
	4-HO-McPMT [42]	artificial	4-OH	CH2C3H5	CH3	4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
	4-HO-DPT	artificial	4-OH	CH2CH2CH3	CH2CH2CH3	4-hydroxy-N,N-dipropyltryptamine	63065-88-3
	4-AcO-DPT	artificial	4-OCOCH3	CH2CH2CH3	CH2CH2CH3	4-acetoxy-N,N-dipropyltryptamine	1445751-75-6
	4-HO-PiPT	artificial	4-OH	CH2CH2CH3	CH(CH3)2	4-hydroxy-N-propyl-N-isopropyltryptamine
	4-AcO-PiPT	artificial	4-OCOCH3	CH2CH2CH3	CH(CH3)2	4-acetoxy-N-propyl-N-isopropyltryptamine
	4-HO-DiPT	artificial	4-OH	CH(CH3)2	CH(CH3)2	4-hydroxy-N,N-diisopropyltryptamine	132328-45-1
	4-AcO-DiPT	artificial	4-OCOCH3	CH(CH3)2	CH(CH3)2	4-acetoxy-N,N-diisopropyltryptamine	936015-60-0
	4-PrO-DiPT	artificial	4-OCOCH2CH3	CH(CH3)2	CH(CH3)2	4-propionyloxy-N,N-diisopropyltryptamine	1373882-13-3
	Luvesilocin (RE104; FT-104)	artificial	4-OCO(CH2)3COOH	CH(CH3)2	CH(CH3)2	4-glutaryloxy-N,N-diisopropyltryptamine
	4-PO-DiPT	artificial	4-OPO3H2	CH(CH3)2	CH(CH3)2	4-phosphoryloxy-N,N-diisopropyltryptamine	1373882-09-7
	4-HO-DALT	artificial	4-OH	H2C=CH-CH2	H2C=CH-CH2	4-hydroxy-N,N-diallyltryptamine	2173386-70-2
	4-AcO-DALT	artificial	4-OCOCH3	H2C=CH-CH2	H2C=CH-CH2	4-acetoxy-N,N-diallyltryptamine	1445751-71-2
	4-HO-DBT	artificial	4-OH	(CH2)3CH3	(CH2)3CH3	4-hydroxy-N,N-dibutyltryptamine	63065-89-4
	4-HO-DiBT	artificial	4-OH	CH2CH(CH3)2	CH2CH(CH3)2	4-hydroxy-N,N-diisobutyltryptamine
	4-HO-DsBT	artificial	4-OH	CH(CH3)CH2CH3	CH(CH3)CH2CH3	4-hydroxy-N,N-disecbutyltryptamine	127507-01-1
	5-MeO-MET	artificial	5-OCH3	CH2CH3	CH3	5-methoxy-N-Methyl-N-ethyltryptamine	16977-53-0
	5-MeO-DET	artificial	5-OCH3	CH2CH3	CH2CH3	5-methoxy-N,N-diethyltryptamine	2454-70-8
	5-MeO-MPT	artificial	5-OCH3	CH3	CH2CH2CH3	5-methoxy-N-methyl-N-propyltryptamine
	5-MeO-EPT	artificial	5-OCH3	CH2CH3	CH2CH2CH3	5-methoxy-N-ethyl-N-propyltryptamine	850032-67-6
	5-MeO-DPT	artificial	5-OCH3	CH2CH2CH3	CH2CH2CH3	5-methoxy-N,N-dipropyltryptamine	69496-75-9
	5-MeO-MALT	artificial	5-OCH3	H2C=CH-CH2	CH3	5-methoxy-N-Methyl-N-allyltryptamine	1373918-64-9
	5-MeO-DALT	artificial	5-OCH3	H2C=CH-CH2	H2C=CH-CH2	5-methoxy-N,N-diallyltryptamine	928822-98-4
	ASR-3001 (5-MeO-iPALT)	artificial	5-OCH3	H2C=CH-CH2	CH2CH(CH3)2	5-methoxy-N-allyl-N-isopropyltryptamine
	5-MeO-MiPT	artificial	5-OCH3	CH3	CH(CH3)2	5-methoxy-N,N-methylisopropyltryptamine	96096-55-8
	5,6-MeO-MiPT	artificial	5-OCH3, 6-OCH3	CH3	CH(CH3)2	5,6-dimethoxy-N,N-methylisopropyltryptamine
	5-MeO-McPT	artificial	5-OCH3	CH3	C3H5	5-methoxy-N-methyl-N-cyclopropyltryptamine
	5-MeO-McBT	artificial	5-OCH3	CH3	C4H7	5-methoxy-N-methyl-N-cyclobutyltryptamine
	5-MeO-EiPT	artificial	5-OCH3	CH2CH3	CH(CH3)2	5-methoxy-N-ethyl-N-isopropyltryptamine	850032-66-5
	5-MeO-PiPT	artificial	5-OCH3	CH2CH2CH3	CH(CH3)2	5-methoxy-N-propyl-N-isopropyltryptamine
	5-MeO-DiPT	artificial	5-OCH3	CH(CH3)2	CH(CH3)2	5-methoxy-N,N-diisopropyltryptamine	4021-34-5
	5-MeO-DBT	artificial	5-OCH3	(CH2)3CH3	(CH2)3CH3	5-methoxy-N,N-dibutyltryptamine	73785-42-9
	5-MeO-DsBT	artificial	5-OCH3	CH(CH3)CH2CH3	CH(CH3)CH2CH3	5-methoxy-N,N-di-sec-butyltryptamine
	5-MeS-DMT	artificial	5-SCH3	CH3	CH3	5-methylthio-N,N-dimethyltryptamine	5102-11-4
	5-AcO-DMT	artificial	5-OCOCH3	CH3	CH3	5-acetoxy-N,N-dimethyltryptamine	16977-50-7
	5-AcO-MET [43]	artificial	5-OCOCH3	CH3	CH2CH3	5-acetoxy-N-methyl-N-ethyltryptamine
	5-AcO-DET	artificial	5-OCOCH3	CH2CH3	CH2CH3	5-acetoxy-N,N-diethyltryptamine
	5-AcO-EPT [44]	artificial	5-OCOCH3	CH2CH3	CH2CH2CH3	5-acetoxy-N-ethyl-N-propyltryptamine
	5-AcO-DPT	artificial	5-OCOCH3	CH2CH2CH3	CH2CH2CH3	5-acetoxy-N,N-dipropyltryptamine
	5-AcO-MiPT	artificial	5-OCOCH3	CH3	CH(CH3)2	5-acetoxy-N-methyl-N-isopropyltryptamine
	5-AcO-DiPT	artificial	5-OCOCH3	CH(CH3)2	CH(CH3)2	5-acetoxy-N,N-diisopropyltryptamine
	5-Ethoxy-DMT	artificial	5-OCH2CH3	CH3	CH3	5-ethoxy-N,N-dimethyltryptamine	855245-09-9
	5-Ethoxy-MET	artificial	5-OCH2CH3	CH3	CH2CH3	5-ethoxy-N-methyl-N-ethyltryptamine
	5-Ethoxy-DET	artificial	5-OCH2CH3	CH2CH3	CH2CH3	5-ethoxy-N,N-diethyltryptamine
	5-Ethoxy-MPT	artificial	5-OCH2CH3	CH3	CH2CH2CH3	5-ethoxy-N-methyl-N-propyltryptamine
	5-Ethoxy-EPT	artificial	5-OCH2CH3	CH2CH3	CH2CH2CH3	5-ethoxy-N-ethyl-N-propyltryptamine
	5-Ethoxy-DPT	artificial	5-OCH2CH3	CH2CH2CH3	CH2CH3	5-ethoxy-N,N-dipropyltryptamine
	5-Ethoxy-MiPT	artificial	5-OCH2CH3	CH3	CH(CH3)2	5-ethoxy-N-methyl-N-isopropyltryptamine
	5-Ethoxy-EiPT	artificial	5-OCH2CH3	CH2CH3	CH(CH3)2	5-ethoxy-N-ethyl-N-isopropyltryptamine
	5-Ethoxy-DiPT	artificial	5-OCH2CH3	CH(CH3)2	CH(CH3)2	5-ethoxy-N,N-diisopropyltryptamine
	5-Ethoxy-DALT	artificial	5-OCH2CH3	H2C=CH-CH2	H2C=CH-CH2	5-ethoxy-N,N-diallyltryptamine
	5-BnO-DMT	artificial	5-OCH2C6H5	CH3	CH3	5-benzyloxy-N,N-dimethyltryptamine	101832-88-6
	5-HO-DET	artificial	5-OH	CH2CH3	CH2CH3	5-hydroxy-N,N-diethyltryptamine	14009-42-8
	5-HO-DPT	artificial	5-OH	CH2CH2CH3	CH2CH2CH3	5-hydroxy-N,N-dipropyltryptamine	36288-75-2
	5-HO-MiPT	artificial	5-OH	CH3	CH(CH3)2	5-hydroxy-N-methyl-N-isopropyltryptamine
	5-HO-DiPT	artificial	5-OH	CH(CH3)2	CH(CH3)2	5-hydroxy-N,N-diisopropyltryptamine	36288-76-3
	5-Methyl-DMT (5,N,N-TMT)	artificial	5-CH3	CH3	CH3	5,N,N-trimethyltryptamine	22120-39-4
	5-Ethyl-DMT	artificial	5-CH2CH3	CH3	CH3	5-ethyl-N,N-dimethyltryptamine	171783-25-8
	5-Isopropyl-DMT	artificial	5-CH(CH3)2	CH3	CH3	5-isopropyl-N,N-dimethyltryptamine	156281-04-8
	5-(t-Butyl)-DMT [45]	artificial	5-C(CH3)3	CH3	CH3	5-(tert-butyl)-N,N-dimethyltryptamine
	5-Fluoro-DMT	artificial	5-F	CH3	CH3	5-fluoro-N,N-dimethyltryptamine	22120-36-1
	Bretisilocin (5-fluoro-MET; GM-2505)	artificial	5-F	CH3	CH2CH3	5-fluoro-N-methyl-N-ethyltryptamine	2698331-35-8
	5-Fluoro-DET	artificial	5-F	CH2CH3	CH2CH3	5-fluoro-N,N-diethyltryptamine
	5-Fluoro-EPT	artificial	5-F	CH2CH3	CH2CH2CH3	5-fluoro-N-ethyl-N-propyltryptamine
	5-Fluoro-DPT	artificial	5-F	CH2CH2CH3	CH2CH2CH3	5-fluoro-N,N-dipropyltryptamine
	5-Fluoro-PiPT	artificial	5-F	CH2CH2CH3	CH(CH3)2	5-fluoro-N-propyl-N-isopropyltryptamine
	5-Fluoro-PcBT	artificial	5-F	CH2CH2CH3	CH(CH2)3	5-fluoro-N-propyl-N-cyclobutyltryptamine
	5-Fluoro-iPcBT	artificial	5-F	CH(CH3)2	CH(CH2)3	5-fluoro-N-isopropyl-N-cyclobutyltryptamine
	5-Fluoro-DiPT	artificial	5-F	CH(CH3)2	CH(CH3)2	5-fluoro-N,N-diisoproptryptamine
	5-Fluoro-sBALT	artificial	5-F	CH(CH3)CH2CH3	CH2CH=CH2	5-fluoro-N-sec-butyl-N-allyltryptamine
	5-Fluoro-M1MALT	artificial	5-F	CH3	CH(CH3)CH=CH2	5-fluoro-N-methyl-N-(1-methylallyl)tryptamine
	5-Chloro-DMT	artificial	5-Cl	CH3	CH3	5-chloro-N,N-dimethyltryptamine	22120-32-7
	5-Iodo-DMT	artificial	5-I	CH3	CH3	5-iodo-N,N-dimethyltryptamine	22120-38-3
	5-TFM-DMT	artificial	5-CF3	CH3	CH3	5-(trifluoromethyl)-N,N-dimethyltryptamine	2418713-32-1
	5-TFMO-DMT [46]	artificial	5-OCF3	CH3	CH3	5-(trifluoromethoxy)-N,N-dimethyltryptamine
	5-Nitro-DMT [47]	artificial	5-NO2	CH3	CH3	5-nitro-N,N-dimethyltryptamine	69937-13-9
	5-CN-DMT	artificial	5-C≡N	CH3	CH3	5-cyano-N,N-dimethyltryptamine	17380-42-6
	5-CN-DPT	artificial	5-C≡N	CH2CH2CH3	CH2CH2CH3	5-cyano-N,N-dipropyltryptamine	74885-19-1
	Almotriptan	artificial	5-(CH2SO2N(CH2)4)	CH3	CH3	N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine	154323-57-6
	Rizatriptan	artificial	5-(CH2(N3(CH)2))	CH3	CH3	N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine	145202-66-0
	Sumatriptan	artificial	5-(CH2SO2NHCH3)	CH3	CH3	1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide	103628-46-2
	Zolmitriptan	artificial	5-(CHNHC=OOCH2)	CH3	CH3	5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine	139264-17-8
	6-Fluoro-DMT	artificial	6-F	CH3	CH3	6-fluoro-N,N-dimethyltryptamine	1511-31-5
	6-Fluoro-DET [48]	artificial	6-F	CH2CH3	CH2CH3	6-fluoro-N,N-diethyltryptamine	2836-69-3
	6-Chloro-DMT	artificial	6-Cl	CH3	CH3	6-chloro-N,N-dimethyltryptamine	25390-72-1
	6-Methyl-DMT	artificial	6-CH3	CH3	CH3	6,N,N-trimethyltryptamine
	6-Hydroxy-DMT	artificial	6-OH	CH3	CH3	6-hydroxy-N,N-dimethyltryptamine	1476-33-1
	6-Hydroxy-DET	artificial	6-OH	CH3	CH3	6-hydroxy-N,N-diethyltryptamine	1476-59-1
	6-Methoxy-DMT	artificial	6-OCH3	CH3	CH3	6-methoxy-N,N-dimethyltryptamine	2426-88-2
	7-Methyl-DMT	artificial	7-CH3	CH3	CH3	7,N,N-trimethyltryptamine	65882-39-5
	7-Ethyl-DMT	artificial	7-CH2CH3	CH3	CH3	7-ethyl-N,N-dimethyltryptamine
	7-Chloro-DMT	artificial	7-Cl	CH3	CH3	7-chloro-N,N-dimethyltryptamine
	7-Bromo-DMT [49]	artificial	7-Br	CH3	CH3	7-bromo-N,N-dimethyltryptamine	74798-68-8
	7-Methoxy-DMT	artificial	7-OCH3	CH3	CH3	7-methoxy-N,N-dimethyltryptamine
	7-Methoxy-MiPT	artificial	7-OCH3	CH3	CH(CH3)2	7-methoxy-N-methyl-N-isopropyltryptamine
	1-Methylpsilocin	artificial	1-CH3, 4-OH	CH3	CH3	1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole	1465-16-3
	1-Methyl-5-MeO-DiPT	artificial	1-CH3, 5-OCH3	CH(CH3)2	CH(CH3)2	1-methyl-5-methoxy-N,N-diisopropyltryptamine	1373882-10-0
	NBoc-DMT	artificial	1-OCOC(CH3)3	CH3	CH3	1-(t-butoxycarbonyl)-N,N-dimethyltryptamine
	NB-5-MeO-MiPT	artificial	1-OCOC(CH3)3, 5-OCH3	CH3	CH(CH3)2	1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
	NB-5-MeO-DALT	artificial	1-OCOC(CH3)3, 5-OCH3	H2C=CH-CH2	H2C=CH-CH2	1-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine
	6-Fluoropsilocin	artificial	4-OH,6-F	CH3	CH3	4-hydroxy-6-fluoro-N,N-dimethyltryptamine	312314-12-8
	6-Fluoro-5-MeO-DMT	artificial	5-OCH3,6-F	CH3	CH3	5-methoxy-6-fluoro-N,N-dimethyltryptamine
	5,6-Difluoro-EPT	artificial	5-F, 6-F	CH2CH3	CH2CH2CH3	5,6-difluoro-N-ethyl-N-propyltryptamine
	5-MeO-2-TMT	artificial	2-CH3, 5-OCH3	CH3	CH3	2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine	67292-68-6
	5-MeO-7-TMT	artificial	5-OCH3, 7-CH3	CH3	CH3	5-Methoxy-7,N,N-trimethyltryptamine	61018-77-7
	5-MeO-4-TMT	artificial	4-CH3, 5-OCH3	CH3	CH3	5-Methoxy-4,N,N-trimethyltryptamine
	4-HO-5-MeO-DMT (psilomethoxin)	artificial	4-OH, 5-OCH3	CH3	CH3	4-Hydroxy-5-methoxy-N,N-dimethyltryptamine	2433-31-0
	4-F-5-MeO-DMT	artificial	4-F, 5-OCH3	CH3	CH3	4-Fluoro-5-Methoxy-N,N-dimethyltryptamine	312314-18-4
	5-MeO-7-F-MET	artificial	5-OCH3, 7-F	CH3	CH2CH3	5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
	EMDT (2-ethyl-5-MeO-DMT)	artificial	2-CH2CH3, 5-OCH3	CH3	CH3	2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine	263744-72-5
	ST-1936 (2-methyl-5-chloro-DMT)	artificial	2-CH3, 5-Cl	CH3	CH3	2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine	1210-81-7
	O-4310 (1-isopropyl-6-fluoropsilocin)	artificial	1-CH(CH3)2, 4-OH, 6-F	CH3	CH3	3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol	885671-63-6
	CP-132,484 (4,5-DHP-1-Me-T)	artificial	1-methyl-4,5-(OCH2CH2CH2)	H	H	1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole	143508-76-3
	4,5-DHP-DMT	artificial	4,5-(OCH2CH2CH2)	CH3	CH3	1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole	135360-97-3
	4,5-DHF-DMT (P-3)	artificial [50]	4,5-(CH2CH2O)	CH3	CH3	2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
	4,5-Methylbenzoxazole-DMT (P-131)	artificial	4,5-(OC(CH3)=N)	CH3	CH3	N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine
	4,5-MDO-DMT	artificial	4,5-(OCH2O)	CH3	CH3	2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine	81249-30-1
	4,5-MDO-DiPT	artificial	4,5-(OCH2O)	CH(CH3)2	CH(CH3)2	N-[2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine	82173-82-8
	5,6-FUR-DMT (P-4)	artificial	5,6-(CH=CHO)	CH3	CH3	2-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine
	5,6-MDO-DMT	artificial	5,6-(OCH2O)	CH3	CH3	2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine
	5,6-MDO-MiPT	artificial	5,6-(OCH2O)	CH3	CH(CH3)2	N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine
	5,6-MDO-DiPT	artificial	5,6-(OCH2O)	CH(CH3)2	CH(CH3)2	N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine
Structure	Short Name	Origin	Ring Substitution	RN1	RN2	Full Name	CAS #

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. ^{[51] [52] [53]} 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. ^[53] This is analogous to α-methylation of phenethylamine into amphetamine. ^[53]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors, ^{[54] [55] [56] [57]} and produce psychostimulant, entactogen, and/or psychedelic effects. ^{[51] [52] [53]} 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. ^{[52] [53]} 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. ^[58]

Structure	Name	Chemical name	CAS #
	Tryptophan	(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid	73-22-3
	5-Hydroxytryptophan (5-HTP)	2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid	4350-09-8
	αMT (AMT; Indopan)	1-(1H-Indol-3-yl)propan-2-amine	299-26-3
	4-HO-αMT	3-(2-aminopropyl)-1H-indol-4-ol	15066-09-8
	4-Methyl-αMT	1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine	3569-29-7
	5-Fluoro-αMT	1-(5-fluoro-1H-indol-3-yl)propan-2-amine	712-08-3
	5-Chloro-αMT	1-(5-Chloro-1H-indol-3-yl)propan-2-amine	712-07-2
	5-HO-αMT (αMS/α-methyl-5-HT)	3-(2-aminopropyl)-1H-indol-5-ol	304-52-9
	5-MeO-αMT	1-(5-methoxy-1H-indol-3-yl)propan-2-amine	1137-04-8
	5-Ethoxy-αMT	1-(5-ethoxy-1H-indol-3-yl)propan-2-amine	101832-83-1
	5-Isopropoxy-αMT	1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine
	5-Allyloxy-αMT	1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine
	BW-723C86	1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine	160521-72-2
	6-Fluoro-αMT	1-(6-fluoro-1H-indol-3-yl)propan-2-amine	712-11-8
	7-Chloro-AMT	1-(7-chloro-1H-indol-3-yl)propan-2-amine	711-99-9
	AL-37350A (4,5-DHP-αMT)	(S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole	362603-40-5
	Compound 5 [59]	1-(3H-benzo[e]indol-1-yl)propan-2-amine
	αET	1-(1H-indol-3-yl)butan-2-amine	2235-90-7
	4-Methyl-αET	1-(4-Methyl-1H-indol-3-yl)butan-2-amine	28289-30-7
	4-HO-αET	1-(4-hydroxy-1H-indol-3-yl)butan-2-amine	28289-28-3
	5-Fluoro-αET	1-(5-fluoro-1H-indol-3-yl)butan-2-amine	1380137-98-3
	5-Methyl-αET	1-(5-methyl-1H-indol-3-yl)butan-2-amine	1380148-21-9
	5-MeO-αET	1-(5-methoxy-1H-indol-3-yl)butan-2-amine	4765-10-0
	7-Methyl-αET	1-(7-methyl-1H-indol-3-yl)butan-2-amine	13712-80-6
	N-Methyl-5-MeO-αMT (α,N,O-TMS/α,N,O-trimethyl-5-HT)	[1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine	4822-13-3
	Indolylpropylaminopentane (IPAP; α,N-DPT)	1-(1H-indol-3-yl)-N-propylpentan-2-amine
	N,N-Dimethyl-αMT (α,N,N-TMT)	(2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine	4761-32-4
	N,N-Dimethyl-5-MeO-αMT (5-MeO-α,N,N-TMT)	(2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine	101831-90-7
	α-Methyl-DiPT	(2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
	MPMI [60]	3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole	143321-54-4
	Lucigenol (4-HO-MPMI)	(R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole	250672-65-2
	5-MeO-MPMI (CP-108509)	5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole	143321-57-7
	5F-MPMI [61]	(R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole
	5-Br-MPMI	5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole	143322-57-0
	Eletriptan	3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole	143322-58-1
	Z5247692566 [35] [62]	4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine
	BK-NM-AMT (α,N-dimethyl-β-ketotryptamine) [63] [64] [65]	1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
	BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine) [66] [67] [68] [65]	1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one
	BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine) [68] [69] [70]	1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one
	BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine) [68] [71] [72]	1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one

List of substituted β-ketotryptamines

A number of β-ketotryptamines (beta-ketotryptamines) are known. ^{[63] [65] [68]} 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. ^{[63] [65] [68]} They act as monoamine releasing agents. ^{[63] [65] [68]}

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
• Piperidinylethylindoles like pip-T
• Pyrrolidinylethylindoles like pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, and 4-F-5-MeO-pyr-T
• Pyrrolidinylmethylindoles like MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-135807, and eletriptan
• Tetrahydropyridinylindoles like RS134-49 (4-Me-THPI), RU-28253 (5-MeO-THPI), and NEtPhOH-THPI
• Tetrahydrocarbazolamines like ciclindole, flucindole, frovatriptan, LY-344864, and ramatroban
• Tetrahydropyrroloquinolines like bufothionine and O-methylnordehydrobufotenine
• Others like barettin, cyclic 3-hydroxymelatonin, and metralindole

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

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

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.

Structure	Name	Chemical name	CAS #
	C-DMT [73]	2-(3H-inden-1-yl)-N,N-dimethylethanamine
	Dimemebfe (5-MeO-BFE)	2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine	140853-58-3
	5-MeO-DiBF	N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
	3-APB	3-(2-aminopropyl)benzofuran	105909-13-5
	3-APBT (SKF-6678)	1-(1-benzothiophen-3-yl)propan-2-amine	1201-27-0
	Mebfap (5-MeO-3-APB)	3-(2-aminopropyl)-5-methoxybenzofuran	140853-59-4
	Isotryptamine (isoT)	2-indol-1-ylethanamine	13708-58-2
	isoAMT	1-indol-1-ylpropan-2-amine	1227465-67-9
	(S)-5,6-Difluoro-isoAMT [74]	(S)-1-(5,6-difluoroindol-1-yl)propan-2-amine
	Ro60-0175 ((S)-5-F-6-Cl-isoAMT)	(S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine	169675-09-6
	isoDMT	2-indol-1-yl-N,N-dimethylethanamine	87482-09-5
	5-MeO-isoDMT	2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine	244122-80-3
	6-MeO-isoDMT	2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine	87482-11-9
	Zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-Me-isoDMT)	(2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine	2481740-94-5
	2ZEDMA	2-indolizin-1-yl-N,N-dimethylethanamine
	1ZP2MA	1-indolizin-1-yl-N-methylpropan-2-amine
	1Z2MAP1O	1-indolizin-3-yl-2-(methylamino)propan-1-one	2110204-31-2
	Example 16 [75] [76]	1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
	Example 1 [77]	1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine
	VER-3323	(2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine	259857-99-3
	AL-34662 (indazole-5-HO-AMT)	1-((S)-2-Aminopropyl)-1H-indazol-6-ol	210580-75-9
	O-Methyl-AL-34662 (indazole-5-MeO-AMT)	1-((S)-6-methoxy-2-aminopropyl)-1H-indazole	210580-60-2
	7-Methyl-AL-34662	1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol	874668-67-4
	7-Chloro-AL-34662	1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol	874881-86-4
	AL-38022A	(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine	478132-11-5
	Example 9 [78]	(S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine	478132-12-6
	Example 3 [79]	(S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine	890087-75-9
	Example 1 [80]	(S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine	1373917-69-1
	YM-348	(2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine	372163-84-3
	2-Desethyl-YM-348 [81]	(2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine	748116-94-1
	I-32 [82]	3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
	2-Azapsilocin (Psilocin indazole analogue, P-6) [83]	3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol
	4-Aza-5-MeO-DPT (P-11)	N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine
	5-Aza-4-MeO-DiPT (P-36)	N-[2-(4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
	7-Aza-5-MeO-DiPT (P-19)	N-[2-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
	RS134-49 (4-Me-THPI)	4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole	2945139-94-4
	RU-28253 (5-MeO-THPI)	5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole
	NEtPhOH-THPI (compound 24c)	3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole
	VU6067416 [84]	3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole	3027515-24-5
	(R)-69	3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine	2765652-48-8
	SN-22	3-(1-methylpiperidin-4-yl)-1H-indole	17403-07-5
	RU-24,969	5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole	107008-28-6
	EMD-386088	5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole	54635-62-0

Overview table

• v
• t
• e

Simple tryptamines and their common derivatives

Simple	4-Hydroxy	4-Acetoxy	5-Methoxy	5-Hydroxy
Tryptamine (T)	4-HO-T (dinorpsilocin)	4-AcO-T	5-MeO-T (O-methylserotonin)	5-HO-T (serotonin; 5-HT)
NAcT	4-HO-NAcT	4-AcO-NAcT	5-MeO-NAcT (melatonin)	5-HO-NAcT (normelatonin; NAS)
NMT	4-HO-NMT (norpsilocin)	4-AcO-NMT	5-MeO-NMT	5-HO-NMT (N-methylserotonin)
NET	4-HO-NET	4-AcO-NET	5-MeO-NET	5-HO-NET
NPT	4-HO-NPT	4-AcO-NPT	5-MeO-NPT	5-HO-NPT
NiPT	4-HO-NiPT	4-AcO-NiPT	5-MeO-NiPT	5-HO-NiPT
NALT	4-HO-NALT	4-AcO-NALT	5-MeO-NALT	5-HO-NALT
NBT	4-HO-NBT	4-AcO-NBT	5-MeO-NBT	5-HO-NBT
NiBT	4-HO-NiBT	4-AcO-NiBT	5-MeO-NiBT	5-HO-NiBT
NsBT	4-HO-NsBT	4-AcO-NsBT	5-MeO-NsBT	5-HO-NsBT
NtBT	4-HO-NtBT	4-AcO-NtBT	5-MeO-NtBT	5-HO-NtBT
NAT	4-HO-NAT	4-AcO-NAT	5-MeO-NAT	5-HO-NAT
NHT	4-HO-NHT	4-AcO-NHT	5-MeO-NHT	5-HO-NHT
NcPT	4-HO-NcPT	4-AcO-NcPT	5-MeO-NcPT	5-HO-NcPT
NBnT	4-HO-NBnT	4-AcO-NBnT	5-MeO-NBnT	5-HO-NBnT
NBOMeT	4-HO-NBOMeT	4-AcO-NBOMeT	5-MeO-NBOMeT	5-HO-NBOMeT
NB3OMeT	4-HO-NB3OMeT	4-AcO-NB3OMeT	5-MeO-NB3OMeT	5-HO-NB3OMeT
DMT	4-HO-DMT (psilocin)	4-AcO-DMT (psilacetin)	5-MeO-DMT (mebufotenin)	5-HO-DMT (bufotenin)
DET	4-HO-DET (ethocin)	4-AcO-DET (ethacetin)	5-MeO-DET	5-HO-DET
DPT	4-HO-DPT (deprocin)	4-AcO-DPT (depracetin)	5-MeO-DPT	5-HO-DPT (DiPS, NDPS)
DiPT	4-HO-DiPT (iprocin)	4-AcO-DiPT (ipracetin)	5-MeO-DiPT (foxy)	5-HO-DiPT
DALT	4-HO-DALT (daltocin)	4-AcO-DALT (dalcetin)	5-MeO-DALT (foxtrot)	5-HO-DALT
DBT	4-HO-DBT	4-AcO-DBT	5-MeO-DBT	5-HO-DBT
DiBT	4-HO-DiBT	4-AcO-DiBT	5-MeO-DiBT	5-HO-DiBT
DsBT	4-HO-DsBT	4-AcO-DsBT	5-MeO-DsBT	5-HO-DsBT
DtBT	4-HO-DtBT	4-AcO-DtBT	5-MeO-DtBT	5-HO-DtBT
DAT	4-HO-DAT	4-AcO-DAT	5-MeO-DAT	5-HO-DAT
DHT	4-HO-DHT	4-AcO-DHT	5-MeO-DHT	5-HO-DHT
DcPT	4-HO-DcPT	4-AcO-DcPT	5-MeO-DcPT	5-HO-DcPT
MET	4-HO-MET (metocin)	4-AcO-MET (metacetin)	5-MeO-MET	5-HO-MET
MPT	4-HO-MPT (meprocin)	4-AcO-MPT	5-MeO-MPT	5-HO-MPT
MiPT	4-HO-MiPT (miprocin)	4-AcO-MiPT (mipracetin)	5-MeO-MiPT (moxy)	5-HO-MiPT
MALT	4-HO-MALT (maltocin)	4-AcO-MALT	5-MeO-MALT	5-HO-MALT
MBT	4-HO-MBT	4-AcO-MBT	5-MeO-MBT	5-HO-MBT
MiBT	4-HO-MiBT	4-AcO-MiBT	5-MeO-MiBT	5-HO-MiBT
MsBT	4-HO-MsBT	4-AcO-MsBT	5-MeO-MsBT	5-HO-MsBT
MtBT	4-HO-MtBT	4-AcO-MtBT	5-MeO-MtBT	5-HO-MtBT
McPT	4-HO-McPT	4-AcO-McPT	5-MeO-McPT	5-HO-McPT
McPMT	4-HO-McPMT	4-AcO-McPMT	5-MeO-McPMT	5-HO-McPMT
McPeT	4-HO-McPeT	4-AcO-McPeT	5-MeO-McPeT	5-HO-McPeT
EPT	4-HO-EPT (eprocin)	4-AcO-EPT	5-MeO-EPT	5-HO-EPT
EiPT	4-HO-EiPT (eiprocin)	4-AcO-EiPT	5-MeO-EiPT	5-HO-EiPT
EALT	4-HO-EALT	4-AcO-EALT	5-MeO-EALT	5-HO-EALT
EBT	4-HO-EBT	4-AcO-EBT	5-MeO-EBT	5-HO-EBT
EiBT	4-HO-EiBT (eibucin)	4-AcO-EiBT	5-MeO-EiBT	5-HO-EiBT
EsBT	4-HO-EsBT	4-AcO-EsBT	5-MeO-EsBT	5-HO-EsBT
EtBT	4-HO-EtBT	4-AcO-EtBT	5-MeO-EtBT	5-HO-EtBT
EcPT	4-HO-EcPT	4-AcO-EcPT	5-MeO-EcPT	5-HO-EcPT
PiPT	4-HO-PiPT (piprocin)	4-AcO-PiPT	5-MeO-PiPT	5-HO-PiPT
PALT	4-HO-PALT	4-AcO-PALT	5-MeO-PALT	5-HO-PALT
PBT	4-HO-PBT	4-AcO-PBT	5-MeO-PBT	5-HO-PBT
PiBT	4-HO-PiBT	4-AcO-PiBT	5-MeO-PiBT	5-HO-PiBT
PsBT	4-HO-PsBT	4-AcO-PsBT	5-MeO-PsBT	5-HO-PsBT
PtBT	4-HO-PtBT	4-AcO-PtBT	5-MeO-PtBT	5-HO-PtBT
PcPT	4-HO-PcPT	4-AcO-PcPT	5-MeO-PcPT	5-HO-PcPT
iPALT (ALiPT)	4-HO-iPALT	4-AcO-iPALT	5-MeO-iPALT (ASR-3001)	5-HO-iPALT
iPBT	4-HO-iPBT	4-AcO-iPBT	5-MeO-iPBT	5-HO-iPBT
iPiBT	4-HO-iPiBT	4-AcO-iPiBT	5-MeO-iPiBT	5-HO-iPiBT
iPsBT	4-HO-iPsBT	4-AcO-iPsBT	5-MeO-iPsBT	5-HO-iPsBT
iPtBT	4-HO-iPtBT	4-AcO-iPtBT	5-MeO-iPtBT	5-HO-iPtBT
iPcPT	4-HO-iPcPT	4-AcO-iPcPT	5-MeO-iPcPT	5-HO-iPcPT
TMT	4-HO-TMT	4-AcO-TMT	5-MeO-TMT	5-HO-TMT
Pyr-T	4-HO-pyr-T	4-AcO-pyr-T	5-MeO-pyr-T	5-HO-pyr-T
Pip-T	4-HO-pip-T	4-AcO-pip-T	5-MeO-pip-T	5-HO-pip-T
MPMI	4-HO-MPMI (lucigenol)	4-AcO-MPMI	5-MeO-MPMI (CP-108509)	5-HO-MPMI
THPI	4-HO-THPI	4-AcO-THPI	5-MeO-THPI (RU-28253)	5-HO-THPI
Notes: (1) Other notable acyloxy derivatives of the above include 4-PrO-DMT, 4-PrO-DiPT, 4-PrO-MET, 4-GO-DMT, and 4-GO-DiPT (luvesilocin). (2) 4-Phosphoroxy derivatives of the above include norbaeocystin (4-PO-T), baeocystin (4-PO-NMT), psilocybin (4-PO-DMT), ethocybin (4-PO-DET), 4-PO-DiPT, 4-PO-MET, and aeruginascin (4-PO-TMT). (3) α-Alkyl derivatives of the above are as follows: Tryptamine: AMT, AET, 4-HO-AMT, 4-HO-AET, 5-MeO-AMT, 5-MeO-AET, and 5-HO-AMT (α-methylserotonin); NMT: α,N-DMT and α,N,O-TMS; NPT: IPAP (α,N-DPT); DMT: α,N,N-TMT and α,N,N,O-TeMS; and no others for the rest.

See also

• Substituted β-carboline
• Ibogalog
• Iboga alkaloid
• Lysergamide
• TiHKAL
• List of miscellaneous 5-HT_2A receptor agonists
• Substituted isotryptamine
• Indazolylethylamine
• Indolizinylethylamine
• Tetrahydropyridinylpyrrolopyridine
• Substituted 2-aminoindane
• Substituted amphetamine
• Substituted benzofuran
• Substituted cathinone
• Substituted methylenedioxyphenethylamine
• Substituted phenethylamine
• 2C, DOx, 25-NB

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