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Substituted tryptamine

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(Redirected from Cyclized 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

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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

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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
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 MAOITooltip 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

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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

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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

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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 MAOITooltip 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

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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 4-Hydroxy-α-methyltryptamine 15–20 mg+ Unknown
4-Methyl-AMT 4-Methyl-α-methyltryptamine 20–60 mg+ Unknown
5-Fluoro-AMT 5-Fluoro-α-methyltryptamine 25 mg+ >9 hours
6-Fluoro-AMT 6-Fluoro-α-methyltryptamine 25–75 mg "Long"
α-Methylserotonin (AMS; 5-HO-AMT) α-Methyl-5-hydroxytryptamine Unknown Unknown
α,O-DMS (5-MeO-AMT) α-Methyl-5-methoxytryptamine 2.5–5 mg (0.5–15 mg) 12–18 hours
α,N,O-TMS (5-MeO-N-methyl-AMT) α-Methyl-5-methoxy-N-methyltryptamine 10–20 mg 6–8 hours
α,N,N,O-TeMS (5-MeO-N,N-dimethyl-AMT) 5-Methoxy-α,N,N-trimethyltryptamine Unknown Unknown
5-MeO-AET α-Ethyl-5-methoxytryptamine ~70 mg Several hours
Bk-NM-AMT (β-keto-N-methyl-AMT)e α-Methyl-β-keto-N-methyltryptamine Unknown Unknown
Footnotes: a = AMT is a not only 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

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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-MiPT 4-Methoxy-N-methyl-N-isopropyltryptamines 20–30 mg 4–6 hours
4,5-MDO-DMT 4,5-Methylenedioxy-N,N-dimethyltryptamine Unknown Unknown
4,5-MDO-DiPT 4,5-Methylenedioxy-N,N-diisopropyltryptamine >25 mg Unknown
5-Fluoro-DMT 5-Fluoro-N,N-dimethyltryptamine Unknown Unknown
5-Bromo-DMT 5-Bromo-N,N-dimethyltryptamine Unknowna Unknown
Bretisilocin (5-fluoro-MET) 5-Fluoro-N-methyl-N-ethyltryptamine Unknownb Unknownb
5-MeO-2-TMT 5-Methoxy-2-methyl-N,N-dimethyltryptamine 75–150 mg 5–10 hours
5-MeS-DMT 5-Methylthio-N,N-dimethyltryptamine Unknownc Unknownc
5,6-MeO-MiPT 5,6-Dimethoxy-N-methyl-N-isopropyltryptamine >75 mg Unknown
5,6-MDO-DMT 5,6-Methylenedioxy-N,N-dimethyltryptamine >5 mg Unknown
5,6-MDO-DiPT 5,6-Methylenedioxy-N,N-diisopropyltryptamine Unknown Unknown
5,6-MDO-MiPT 5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine >50–60 mg Unknown
6-Fluoro-DMT 6-Fluoro-N,N-dimethyltryptamine Unknown Unknown
6-Fluoro-DET 6-Fluoro-N,N-diethyltryptamine >80 mg Unknown
6-HO-DMT 6-Hydroxy-N,N-dimethyltryptamine >80 mg Unknown
6-MeO-DiPT 6-Methoxy-N,N-diisopropyltryptamine >50 mg Unknown
6-MeO-MiPT 6-Methoxy-N-methyl-N-isopropyltryptamine >50 mg Unknown
7-MeO-DiPT 7-Methoxy-N,N-diisopropyltryptamine >70 mg Unknown
7-MeO-MiPT 7-Methoxy-N-methyl-N-isopropyltryptamine >70 mg Unknown
Footnotes: 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 <1 hour. Refs: [3][4][2][9][11] Individual: [31][32]

Interactions

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

List of substituted tryptamines

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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

[edit]

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

[edit]

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

[edit]

Examples of cyclized tryptamines include:

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

[edit]

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

[edit]
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

[edit]

References

[edit]
  1. ^ Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable". phys.org. Retrieved 2022-12-26.
  2. ^ a b c d e f g h Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  3. ^ a b c d e f g Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.
  4. ^ a b c d e f g Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.
  5. ^ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
  6. ^ Alexander T. Shulgin (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
  7. ^ a b c d e Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC 6165951. PMID 29850881.
  8. ^ a b c d e Halberstadt, Adam L.; Chatha, Muhammad; Klein, Adam K.; Wallach, Jason; Brandt, Simon D. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
  9. ^ a b c d e Ballentine, Galen; Friedman, Samuel Freesun; Bzdok, Danilo (March 2022). "Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences". Sci Adv. 8 (11) eabl6989. Bibcode:2022SciA....8L6989B. doi:10.1126/sciadv.abl6989. PMC 8926331. PMID 35294242.
  10. ^ Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl). 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC 9166850. PMID 35487983.
  11. ^ a b c d e f g McKenna DJ, Towers GH (1984). "Biochemistry and pharmacology of tryptamines and beta-carbolines. A minireview". J Psychoactive Drugs. 16 (4): 347–358. doi:10.1080/02791072.1984.10472305. PMID 6394730.
  12. ^ Nen (4 December 2011). Entheogenic effects of NMT from Acacia. Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011 (PDF). Archived from the original on 5 April 2025. Retrieved 15 April 2025.{{cite conference}}: CS1 maint: bot: original URL status unknown (link)
  13. ^ Nen (13 July 2013). NMT: A Spatial Hallucinogen With Therapeutic Applications. Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013.
  14. ^ a b Liechti ME, Holze F (2022). "Dosing Psychedelics and MDMA". Curr Top Behav Neurosci. 56: 3–21. doi:10.1007/7854_2021_270. PMID 34734392.
  15. ^ a b c Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
  16. ^ Barker SA (June 2022). "Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT". Psychopharmacology (Berl). 239 (6): 1749–1763. doi:10.1007/s00213-022-06065-0. PMC 8782705. PMID 35064294. Doses for vaporized or inhaled free-base DMT are typically 40–50 mg, although larger doses have been reported (100 mg; Shulgin and Shulgin 1997). Pallavicini et al. (2021) have reported that vaporization of approximately 40 mg of DMT, administered in a natural setting, produced potential electroencephalographic markers of mystical-type experiences in 35 volunteers. The onset of effects for inhaled DMT is rapid, similar to that of IV administration, but lasts less than 30 min (Riba et al. 2015; Davis et al. 2020). [...] For administration of pharmahuasca, 50 mg DMT:100 mg harmaline is usually the recommended dosage. However, combinations of 50 mg harmaline:50 mg harmine and 50 mg DMT have been tested with success. The harmalas and DMT are typically put into separate gelatin capsules, with the harmaline/harmine being taken first and the DMT being taken 15 to 20 min later. The use of moclobemide, a reversible inhibitor of MAO-A, has also been reported in DMT "pharmahuasca" studies (Kaasik et al. 2020; Ruffell et al. 2020).
  17. ^ Egger K, Aicher HD, Cumming P, Scheidegger M (September 2024). "Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors". Cell Mol Life Sci. 81 (1): 395. doi:10.1007/s00018-024-05353-6. PMC 11387584. PMID 39254764. Recent studies tested i.v. DMT with different administration regimens. Such protocols entailed 0–19.2 mg bolus 0.5–0.8 mg/min constant infusion of DMT freebase (as hemifumarate) for up to 90 min (Basel) [7], 11.2 mg bolus 1.2 mg/min infusion of DMT freebase (as fumarate) for up to 30 min (London) [8], and constant infusion totaling 13.4 mg DMT freebase (as fumarate) over 10 min (London) [110]). [...] The various β-carbolines in B. caapi, especially harmine and harmaline, enable the attainment of sufficient plasma DMT concentrations to evoke psychedelic effects lasting 4–6 h [5, 61].
  18. ^ a b Ott J (1999). "Pharmahuasca: human pharmacology of oral DMT plus harmine". J Psychoactive Drugs. 31 (2): 171–177. doi:10.1080/02791072.1999.10471741. PMID 10438001. Since the β-carbolines per se could not explain the legendary psychoptic (visionary) activity of the jungle ambrosia, this had to be due to its DMT content, which amounted to an average of 29 mg/dose in the 16 potions analyzed (range: 25-36 mg/dose). [...] TABLE 1 Human Pharmacology of Psychoptic Tryptamines [...]
  19. ^ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.
  20. ^ Szara S, Hearst E (1962). "The 6-Hydroxylation of Tryptamine Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences. 96 (1): 134–141. Bibcode:1962NYASA..96..134S. doi:10.1111/j.1749-6632.1962.tb50108.x. The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.
  21. ^ Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. Szara and co-workers (221,223,225) noted psychotomimetic activity for N,N-diethyltryptamine (DET; 38) at a dose of 1 mg/kg. [...] N,N-Dipropyltryptamine (DPT; 39) is also hallucinogenic in man at 1 mg/kg (222). [...] Branching of the propyl groups results in N,N-diisopropyltryptamine (DIPT; 40), which is orally active at 20 to 50 mg (202). N,N-Dibutyltryptamine (DBT; 41) and N,N-dihexyltryptamine (DHT; 42) have been examined only briefly. At 1 mg/kg, DBT produced only slight perceptual, emotional, and thinking disturbances in man, while DHT at the same dose was completely inactive (222).
  22. ^ Szara. S. (1961): Correlation between metabolism and behavioral action of psychotropic tryptamine derivatives. Biochem. Pharmacol., 8:32. "N.N-dimethyltryptamine and its N.N-diethyl and N.N-dipropyl homologues produce autonomic symptoms, perceptual, emotional, and thinking disturbances in man (in doses of 1 mg/kg) similar to LSD25 or mescalin but for a much shorter period of time. The corresponding dibutyl derivative causes only very slight symptoms while the dihexyl compound is completely inactive in the same dose."
  23. ^ Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences. 21 (23): 9279. doi:10.3390/ijms21239279. PMC 7730282. PMID 33291798. 4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84].
  24. ^ Ludbrook G, Bryson N, Taylor B, Hocevar-Trnka J, Johnson MW, Hirman J, Morrish G, Alexander R, Pollack M (2025). "Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study". J Clin Psychopharmacol. 45 (5): 441–453. doi:10.1097/JCP.0000000000002047. PMC 12379775. PMID 40685873.
  25. ^ Ott J (2001). "Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine". Journal of Psychoactive Drugs. 33 (3): 273–281. doi:10.1080/02791072.2001.10400574. PMID 11718320. S2CID 5877023.
  26. ^ Ott J (2001). "Shamanic-Snuff Psychonautica: Pharmañopo: Bufotenine—Psychonautics". Shamanic Snuffs or Entheogenic Errhines. Entheobotanica. pp. 99–116 (105–112, 114–115). ISBN 978-1-888755-02-2. OCLC 56061312. Retrieved 24 January 2025.
  27. ^ Hamilton Morris (1 December 2022). "A New One-Hour Talk On 5-MeO-DMT". The Hamilton Morris Podcast. Patreon. Event occurs at 6:27–8:40, 10:15–11:13. Retrieved 21 January 2025. [Morris:] Bufotenine is a drug that I have tried. I've tried isolated pure bufotenine and it is a psychedelic that is both pharmacologically and experientially and chemically intermediate between DMT and 5-MeO-DMT. So it has a longer duration than actually both 5-MeO-DMT and DMT. It's yet less visual than DMT but more visual than 5-MeO-DMT, so it's kind of like in-between the two. It's also very nauseating, which is the main reason that people seem not to enjoy it very much. But it is a classical psychedelic drug that produces visionary effects. And Jonathan Ott actually liked the effect of it quite a bit.
  28. ^ Hamilton Morris (1 September 2021). "PODCAST 28: A talk with Jonathan Ott". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 49:20–50:36. Retrieved 20 January 2025. [Morris:] I've used [bufotenine] a couple times, once at 50 milligrams of the freebase snorted. [...] I found it to be extremely nauseating. I found it to be qualitatively intermediate between 5-MeO-DMT and DMT in that it was more visual than my experiences with 5-MeO-DMT but less visual than my typical experiences with DMT. It had a longer duration than 5-MeO-DMT and maybe even a longer duration than DMT as well. It was about an hour. Although I don't have all that much experience snorting DMT freebase.
  29. ^ "Unusual Analogues: Drugs Used by Gordon Todd Skinner". thislandpress.com. This Land Press. Archived from the original on 17 April 2016. Retrieved 8 April 2016.
  30. ^ Hamilton Morris (29 April 2025). "POD 126: The Return of Psychedelic Selenium with Dr. Josh Hartsel". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 1:33:53–1:35:50. [...] [Hartsel:] The α,N,N-Dimethyl[tryptamine]. [Morris:] Oh yeah, I've made it and tried it actually. [Hartsel:] Oh you did? [Morris:] Yeah, yeah. [Hartsel:] Oh, well what did it do? [Morris:] It is active, it's an active psychedelic. It's reduced potency. I never got it to a dose where it produced particularly interesting effects. I can look up the exact dose. I think it was like... the only thing I remember is that I felt like it was making me sneeze a lot. But it was very pleasant. Nothing bad happened. But the dose just wasn't high enough. I think I took maybe 40 mg. So it was much less potent than AMT orally. The other issue of course is that it could be a prodrug of N-methyl-AMT, which is active, or AMT itself maybe. [...]
  31. ^ Morris H, Wallach J (26 March 2013). "Sea DMT: God Molecule or Barnacle Repellent?". Vice. Retrieved 21 October 2015.
  32. ^ Marek GJ, Makai-Bölöni S, Umbricht D, Christian EP, Winters J, Dvorak D, Raines S, Hughes ZA, Austin EW, Klein AK, Leong W, Krol FJ, Graaf AJV, Juachon MJ, Otto ME, Borghans LGJM, Jacobs G, Kruegel AC, Sporn J. A novel psychedelic 5-HT2A receptor agonist GM-2505: The pharmacokinetic, safety, and pharmacodynamic profile from a randomized trial healthy volunteer. J Psychopharmacol. 2025 Oct 16:2698811251378512. doi:10.1177/02698811251378512 PMID 41099491
  33. ^ Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK (2019). "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE. 14 (1) e0209804. Bibcode:2019PLoSO..1409804T. doi:10.1371/journal.pone.0209804. PMC 6328172. PMID 30629611.
  34. ^ Jensen N. Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. PhD thesis, University of Göttingen, 2004
  35. ^ a b Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, et al. (December 2023). "AlphaFold2 structures template ligand discovery". bioRxiv. doi:10.1101/2023.12.20.572662. PMC 10769324. PMID 38187536.
  36. ^ a b Stirn J, Berger R, Hübner H, Gmeiner P, Klein CD (2025). "Towards "unmakable" psychedelics: SAR exploration of psilocin analogs obtained by a HATU-mediated amide coupling strategy". European Journal of Medicinal Chemistry Reports. 15 100278. doi:10.1016/j.ejmcr.2025.100278.
  37. ^ McKay JB, Parkhurst RM, Silverstein RM, Skinner WA (October 1963). "Analogues of Psilocin and Lysergic acid diethylamide I. Chloro, Nitro, and Amino Derivatives of 3-Substituted Indoles". Canadian Journal of Chemistry. 41 (10): 2585–2590. doi:10.1139/v63-378.
  38. ^ Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC 8033608. PMID 33860183.
  39. ^ Pham DN, Chadeayne AR, Golen JA, Manke DR (February 2021). "Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug". Acta Crystallographica Section E. 77 (Pt 2): 101–106. Bibcode:2021AcCrE..77..101P. doi:10.1107/S2056989021000116. PMC 7869532. PMID 33614134.
  40. ^ Sherwood AM, Burkhartzmeyer EK, Williamson SE, Baumann MH, Glatfelter GC (Jan 2024). "Psychedelic-like Activity of Norpsilocin Analogues". ACS Chem Neurosci. 15 (2): 315–327. doi:10.1021/acschemneuro.3c00610. PMC 10797613. PMID 38189238.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  41. ^ WO 2023115167, Banister S, Jorgensen W, Jinlong T, "Compounds", published 29 June 2023, assigned to Psylo Pty Ltd. 
  42. ^ WO 2021179091, Kozikowski A, Shaprio G, Tueckmantel W, McCorvy J, "3-(2-(Aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-HT2 receptor modulators", published 16 September 2021, assigned to Bright Minds Biosciences Inc. and The Medical College Of Wisconsin Inc. 
  43. ^ WO 2021101926, Stamets PE, "Tryptamine Compositions for Enhancing Neurite Outgrowth.", published 2021-05-27, assigned to Stamets Paul Edward. 
  44. ^ WO 2021168082, Kruegel AC, Sporn J, "Specific Tryptamines for use in the Treatment of Mood Disorders.", published 26 August 2021 
  45. ^ Xu YC, Schaus JM, Walker C, Krushinski J, Adham N, Zgombick JM, Liang SX, Kohlman DT, Audia JE (February 1999). "N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist". Journal of Medicinal Chemistry. 42 (3): 526–31. doi:10.1021/jm9805945. PMID 9986723.
  46. ^ WO 2022235927, Kruegel AC, "Novel Tryptamines and Methods of Treating Mood Disorders", published 10 November 2022, assigned to Gilgamesh Pharmaceuticals, Inc. 
  47. ^ Shaw E, Woolley DW (April 1953). "The synthesis of nitro-and aminoindoles analogous to serotonin". Journal of the American Chemical Society. 75 (8): 1877–1881. doi:10.1021/ja01104a029.
  48. ^ Rabin RA, Regina M, Doat M, Winter JC (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior. 72 (1–2): 29–37. doi:10.1016/s0091-3057(01)00720-1. PMID 11900766. S2CID 6480715.
  49. ^ Glennon RA, Schubert E, Jacyno JM, Rosecrans JA (November 1980). "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry. 23 (11): 1222–6. doi:10.1021/jm00185a014. PMID 6779006.
  50. ^ WO 2023115166, Banister S, Jorgensen W, Jinlong T, "Compounds", published 29 June 2023, assigned to Psylo Pty Ltd. 
  51. ^ a b Ries RK, Miller SC, Fiellin DA (2009). Principles of Addiction Medicine. Lippincott Williams & Wilkins. pp. 216–218. ISBN 978-0-7817-7477-2.
  52. ^ a b c Laing RR (2003). Hallucinogens: A Forensic Drug Handbook. Academic Press. pp. 102–. ISBN 978-0-12-433951-4.
  53. ^ a b c d e Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 641–. ISBN 978-1-60913-345-0.
  54. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  55. ^ Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  56. ^ Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin. 30 (12): 2328–33. doi:10.1248/bpb.30.2328. PMID 18057721.
  57. ^ Feldman JM, Chapman B (December 1975). "Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insluin secretion". Diabetologia. 11 (6): 487–94. doi:10.1007/bf01222097. PMID 1107123.
  58. ^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology. 200 (1): 187–90. doi:10.1016/0014-2999(91)90686-K. PMID 1722753.
  59. ^ Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorganic & Medicinal Chemistry Letters. 12 (2): 155–8. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343.
  60. ^ US 5607951, Macor JE, Wythes MJ, "Indole derivatives", issued 4 March 1997, assigned to Pfizer, Inc. 
  61. ^ WO 2022256554, Wallach J, Dybek M, "Fluorinated Tryptamine Compounds, Analogues Thereof, and Methods Using Same.", published 8 December 2022, assigned to University Of The Sciences. 
  62. ^ Callaway E (18 January 2024). "AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery?". Nature News. 626 (7997): 14–15. Bibcode:2024Natur.626...14C. doi:10.1038/d41586-024-00130-8. PMID 38238624. S2CID 267040499.
  63. ^ a b c d Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB (March 2019). "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology (Berl). 236 (3): 915–924. doi:10.1007/s00213-018-5063-9. PMC 6475490. PMID 30341459.
  64. ^ "1-(1H-indol-3-yl)-2-(methylamino)propan-1-one". PubChem. Retrieved 11 November 2024.
  65. ^ a b c d e US 20240335414, Matthew J. Baggott & Sean Dalziel, "Specialized combinations for mental disorders or mental enhancement", published 10 October 2024, assigned to Tactogen Inc. 
  66. ^ "1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one". PubChem. Retrieved 11 November 2024.
  67. ^ "β-Oxo-5-fluoro-α-methyl-NMT". Isomer Design. 10 November 2024. Retrieved 11 November 2024.
  68. ^ a b c d e f WO 2022061242, Matthew Baggott, "Advantageous tryptamine compositions for mental disorders or enhancement", published 2023 March 24, assigned to Tactogen 
  69. ^ "1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one". PubChem. Retrieved 11 November 2024.
  70. ^ "β-Oxo-5-chloro-α-methyl-NMT". Isomer Design. 10 November 2024. Retrieved 11 November 2024.
  71. ^ "1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one". PubChem. Retrieved 11 November 2024.
  72. ^ "β-Oxo-5-bromo-α-methyl-NMT". Isomer Design. 10 November 2024. Retrieved 11 November 2024.
  73. ^ "PiHKAL·info". Isomer Design. 11 November 2024. Retrieved 31 January 2025.
  74. ^ Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorg Med Chem Lett. 12 (2): 155–158. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343. Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e., S(+)-5,6-difluoro-α-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best, only 10-fold.
  75. ^ Kargbo RB (Jan 2024). "Neuropharmacological Advances: Harnessing 5-HT2A Receptor Modulators and Psychoplastogens". ACS Med Chem Lett. 15 (2): 171–173. doi:10.1021/acsmedchemlett.4c00003. PMC 10860177. PMID 38352827.
  76. ^ Powell NA, Chytil M. Imidazopyridine psychoplastogens and uses thereof. WO 2023/114844
  77. ^ US granted 7012090, Chen HH, May JA, "Pyranoindoles for treating glaucoma", published 17 March 2000, issued 14 March 2006, assigned to Alcon, Inc. 
  78. ^ US granted 6881749, Chen HH, May JA, Severns BS, "Pyranoindazoles and their use for the treatment of glaucoma", published 3 June 2004, issued 19 April 2005, assigned to Alcon, Inc. 
  79. ^ US granted 7425572, Chen HH, May JA, "Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma", published 8 June 2006, issued 16 September 2008, assigned to Alcon, Inc. 
  80. ^ US granted 7268131, Dantanarayana AP, May JA, "Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma", published 15 December 2005, issued 11 September 2007, assigned to Alcon, Inc. 
  81. ^ Shimada I, Maeno K, Kazuta K, Kubota H, Kimizuka T, Kimura Y, et al. (February 2008). "Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists". Bioorganic & Medicinal Chemistry. 16 (4): 1966–82. doi:10.1016/j.bmc.2007.10.100. PMID 18035544.
  82. ^ WO 2022120475, Slassi A, Araujo J, Higgins G, "3-Cyclic Amine-Indole Derivatives as Serotonergic Agents for the Treatment of CNS Disorders.", published 16 June 2022, assigned to Mindset Pharma Inc. 
  83. ^ WO 2023115165, Banister S, Jorgensen W, Jinlong T, "Compounds", published 29 June 2023, assigned to Psylo Pty Ltd. 
  84. ^ Jayakodiarachchi N; et al. (2024). "Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists". ACS Med. Chem. Lett. 15 (2): 302–309. doi:10.1021/acsmedchemlett.3c00566.
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