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Substituted tryptamine

From Wikipedia, the free encyclopedia
(Redirected fromSubstituted α-alkyltryptamine)
Class of indoles
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 simplytryptamines, also known asserotonin analogues (i.e.,5-hydroxytryptamine analogues), areorganic compounds which may be thought of as being derived fromtryptamine itself. The molecular structures of all tryptamines contain anindole ring system, joined to anamino (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 includeserotonin, an importantneurotransmitter, andmelatonin, ahormone involved in regulating the sleep-wake cycle. Tryptaminealkaloids are found infungi,plants andanimals; and sometimes used byhumans for the neurological orpsychotropic effects of the substance. Prominent examples of tryptamine alkaloids includepsilocybin (from "psilocybin mushrooms") andDMT. In South America, dimethyltryptamine is obtained from numerous plant sources, likechacruna, and it is often used inayahuasca brews. Manysynthetic tryptamines have also been made, including themigrainedrugsumatriptan, andpsychedelic 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 examplecyclized tryptamines likeLSD,ibogaine,harmaline,mitragynine andyohimbine. A thorough investigation of dozens of tryptamine compounds was published byAlexander Shulgin andAnn Shulgin in 1997 under the titleTiHKAL (Tryptamines I Have Known and Loved).[2]

Use and effects

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Thedoses,potencies,durations, and effects of psychedelic tryptamines have been reviewed byAlexander 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
CompoundChemical nameDoseDuration
Tryptamine (T)Tryptamine>100 mga
NMTN-MethyltryptamineUnknownb
NETN-EthyltryptamineUnknownUnknown
NiPTN-IsopropyltryptamineUnknownUnknown
NsBTN-sec-Butyltryptamine25–75 mg"Short"
NtBTN-tert-Butyltryptamine5–20 mgUnknown
NATN-Amyltryptamine>100 mg
NHTN-Hexyltryptamine>100 mg
DMTN,N-Dimethyltryptamine>350 mgc
DETN,N-Diethyltryptamine50–150 mg2–4 hours
DPTN,N-Dipropyltryptamine100–250 mg2–4 hours
DiPTN,N-Diisopropyltryptamine25–100 mg (15–150 mg+)6–8 hours
DALTN,N-Diallyltryptamine60–80 mg<3 hours
DBTN,N-Dibutyltryptamine≥100 mgUnknown
DATN,N-DiamyltryptamineUnknownUnknown
DHTN,N-Dihexyltryptamine>100 mg
METN-Methyl-N-ethyltryptamine80–100 mgUnknown
MPTN-Methyl-N-propyltryptamine>50 mgUnknown
MiPTN-Methyl-N-isopropyltryptamine10–25 mg3–4 hours
MBTN-Methyl-N-butyltryptamine250–400 mg4–6 hours
MsBTN-Methyl-N-sec-butyltryptamine250–400 mgUnknown
EPTN-Ethyl-N-propyltryptamineUnknownUnknown
EiPTN-Ethyl-N-isopropyltryptamine24–40 mg4–6 hours
PiPTN-Propyl-N-isopropyltryptamineUnknownUnknown
Pyr-TN,N-TetramethylenetryptamineUnknownUnknown
Footnotes:a =Tryptamine is notorally active, but is activeintravenously at a dose of 250 mg with a very shortduration.b =NMT is not orally active, but is said to be activesmoked at a dose of 50 to 120 mg with a duration of seconds to minutes. Also reportedly orally active with anMAOITooltip monoamine oxidase inhibitor.c =DMT is activeparenterally at doses of 50 to 100 mg (2–100 mg) smoked,intramuscularly, orsubcutaneously and at doses of 4 to 30 mgintravenously (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 anMAOI (as inayahuasca orpharmahuasca), 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
CompoundChemical nameDoseDuration
4-HT (4-HO-T)4-HydroxytryptamineUnknownUnknown
Norbaeocystin (4-PO-T)4-PhosphoryloxytryptamineUnknownUnknown
Norpsilocin (4-HO-NMT)4-Hydroxy-N-methyltryptamineUnknownUnknown
Baeocystin (4-PO-NMT)4-Phosphoryloxy-N-methyltryptamine4–10 mgaUnknown
Psilocin (4-HO-DMT)4-Hydroxy-N,N-dimethyltryptamine10–20 mg (5–40 mg+)3–6 hours
Psilocybin (4-PO-DMT)4-Phosphoryloxy-N,N-dimethyltryptamine10–20 mg (5–40 mg+)3–6 hours
4-AcO-DMT (psilacetin)4-Acetoxy-N,N-dimethyltryptamineUnknownUnknown
4-PrO-DMT4-Propionyloxy-N,N-dimethyltryptamineUnknownUnknown
4-HO-DET (ethocin)4-Hydroxy-N,N-diethyltryptamine10–25 mg4–6 hours
Ethocybin (4-PO-DET)4-Phosphoryloxy-N,N-diethyltryptamine15–30 mg4–6 hours
4-HO-DPT (deprocin)4-Hydroxy-N,N-dipropyltryptamine>20 mg5–8 hours
4-HO-DiPT (iprocin)4-Hydroxy-N,N-diisopropyltryptamine12–20 mg (3–30 mg+)2–3 hours
4-AcO-DiPT (ipracetin)4-Acetoxy-N,N-diisopropyltryptamine6–10 mgUnknown
Luvesilocin (4-GO-DiPT)4-Glutaryloxy-N,N-diisopropyltryptamineUnknownbUnknownb
4-HO-DALT (daltocin)4-Hydroxy-N,N-diallyltryptamineUnknownUnknown
4-HO-DBT4-Hydroxy-N,N-dibutyltryptamine>20 mgUnknown
4-HO-DiBT4-Hydroxy-N,N-diisobutyltryptamine>20 mgUnknown
4-HO-DtBT4-HydroxyN,N-di-tert-butyltryptamineUnknownUnknown
4-HO-MET (metocin)4-Hydroxy-N-methyl-N-ethyltryptamine10–20 mg (2–45 mg+)4–6 hours
4-HO-MPT (meprocin)4-Hydroxy-N-methyl-N-propyltryptamine8–30 mgUnknown
4-HO-MiPT (miprocin)4-Hydroxy-N-methyl-N-isopropyltryptamine12–25 mg (6–30 mg)4–6 hours
4-HO-MALT (maltocin)4-Hydorxy-N-methyl-N-allyltryptamineUnknownUnknown
4-HO-MtBT4-Hydroxy-N-methyl-N-tert-butyltryptamine>15 mgUnknown
4-HO-EPT (eprocin)4-Hydroxy-N-ethyl-N-propyltryptamineUnknownUnknown
4-HO-EiPT4-Hydroxy-N-ethyl-N-isopropyltryptamineUnknownUnknown
4-HO-PiPT (piprocin)4-Hydroxy-N-propyl-N-isopropyltryptamineUnknownUnknown
4-HO-TMT4-Hydroxy-N,N,N-trimethyltryptamineUnknownUnknown
Aeruginascin (4-PO-TMT)4-Phosphoryloxy-N,N,N-trimethyltryptamineUnknownUnknown
4-HO-pyr-T4-Hydroxy-N,N-tetramethylenetryptamine>20 mgUnknown
Footnotes:a =Baeocystin has conflicting reports, some say that it's active and some say that it's inactive.b =Luvesilocin is known to be activesubcutaneously at doses of 5 to 40 mg with an averageduration 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
CompoundChemical nameDoseDuration
Serotonin (5-HT, 5-HO-T)5-Hydroxytryptamine>100 mga
N-Methylserotonin (norbufotenin; 5-HO-NMT)5-Hydroxy-N-methyltryptamineUnknownUnknown
Bufotenin (5-HO-DMT)5-Hydroxy-N,N-dimethyltryptamine>100 mgb
O-Acetylbufotenin (5-AcO-DMT)5-Acetoxy-N,N-dimethyltryptamineUnknownUnknown
O-Pivalylbufotenin (5-t-BuCO-DMT)5-Pivaloxy-N,N-dimethyltryptamineUnknownUnknown
5-HO-DET5-Hydroxy-N,N-diethyltryptamineUnknownUnknown
5-HO-DPT (DiPS, NDPS)5-Hydroxy-N,N-dipropyltryptamineUnknownUnknown
5-HO-DiPT5-Hydroxy-N,N-diisopropyltryptamineUnknownUnknown
Footnotes:a =Serotonin does not cross theblood–brain barrier and is notpsychoactive.b =Bufotenin is notorally active, but is active atintravenously at doses of 8 to 16 mg with aduration of 1 to 2 hours and is active viainsufflation and otherparenteralroutes.Refs:[3][4][2][11]Individual:[25][26][27][28]

5-Methoxytryptamines

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Oral doses and durations of 5-methoxytryptamines
CompoundChemical nameDoseDuration
5-MT (5-MeO-T)5-MethoxytryptamineUnknownUnknown
5-MeO-NMT5-Methoxy-N-methyltryptamineUnknownUnknown
5-MeO-NET5-Methoxy-N-ethyltryptamineUnknownUnknown
5-MeO-NiPT5-Methoxy-N-isopropyltryptamineUnknownUnknown
5-MeO-DMT (mebufotenin)5-Methoxy-N,N-dimethyltryptamine>35 mga
5-MeO-DET5-Methoxy-N,N-diethyltryptamine1–3 mg3–4 hours
5-MeO-DPT5-Methoxy-N,N-dipropyltryptamine6–10 mg2–4 hours
5-MeO-DiPT5-Methoxy-N,N-diisopropyltryptamine6–12 mg4–8 hours
5-MeO-DALT5-Methoxy-N,N-diallyltryptamine12–25 mg2–4 hours
5-MeO-DBT5-Methoxy-N,N-dibutyltryptamineUnknownUnknown
5-MeO-DsBT5-Methoxy-N,N-di-sec-butyltryptamineUnknownUnknown
5-MeO-MET5-Methoxy-N-methyl-N-ethyltryptamineUnknownUnknown
5-MeO-MPT5-Methoxy-N-methyl-N-propyltryptamineUnknownUnknown
5-MeO-MiPT5-Methoxy-N-methyl-N-isopropyltryptamine4–6 mg (0.5–20 mg+)4–6 hours
5-MeO-MALT5-Methoxy-N-methyl-N-allyltryptamineUnknownUnknown
5-MeO-EPT5-Methoxy-N-ethyl-N-propyltryptamineUnknownUnknown
5-MeO-EiPT5-Methoxy-N-ethyl-N-isopropyltryptamineUnknownUnknown
5-MeO-PiPT5-Methoxy-N-propyl-N-isopropyltryptamineUnknownUnknown
ASR-3001 (5-MeO-iPALT)5-Methoxy-N-isopropyl-N-allyltryptamine8–14 mg1.5–2.5 hours
5-MeO-pyr-T5-Methoxy-N,N-tetramethylenetryptamine0.5–2 mgSeveral hours
Melatonin (5-MeO-NAcT)5-Methoxy-N-acetyltryptamine1–10 mgbA few hours
Footnotes:a =5-MeO-DMT is notorally active, but is active at a dose of 2 to 20 mgsmoked or 2 to 3 mgintravenously, with aduration of 5 to 20 minutes. Also orally active with anMAOITooltip monoamine oxidase inhibitor at doses of 10 to 25 mg.b =Melatonin is not a psychedelic but ahypnotic 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
CompoundChemical nameDoseDuration
AMT (α-methyl-T; Indopan)aα-Methyltryptamine15–40 mg12–16 hours
AET (α-ethyl-T; etryptamine; Monase)bα-Ethyltryptamine100–160 mg6–8 hours
α,N-DMT (N-methyl-AMT)cα-Methyl-N-methyltryptamine50–100 mg6–8 hours
α,N,N-TMT (N,N-dimethyl-AMT)α,N,N-TrimethyltryptamineUnknowndUnknown
2,α-DMT (2-methyl-AMT)2-Methyl-α-methyltryptamine300–500 mg7–10 hours
4-HO-AMT4-Hydroxy-α-methyltryptamine15–20 mg+Unknown
4-Methyl-AMT4-Methyl-α-methyltryptamine20–60 mg+Unknown
5-Fluoro-AMT5-Fluoro-α-methyltryptamine25 mg+>9 hours
6-Fluoro-AMT6-Fluoro-α-methyltryptamine25–75 mg"Long"
α-Methylserotonin (AMS; 5-HO-AMT)α-Methyl-5-hydroxytryptamineUnknownUnknown
α,O-DMS (5-MeO-AMT)α-Methyl-5-methoxytryptamine2.5–5 mg (0.5–15 mg)12–18 hours
α,N,O-TMS (5-MeO-N-methyl-AMT)α-Methyl-5-methoxy-N-methyltryptamine10–20 mg6–8 hours
α,N,N,O-TeMS (5-MeO-N,N-dimethyl-AMT)5-Methoxy-α,N,N-trimethyltryptamineUnknownUnknown
5-MeO-AETα-Ethyl-5-methoxytryptamine~70 mgSeveral hours
Bk-NM-AMT (β-keto-N-methyl-AMT)eα-Methyl-β-keto-N-methyltryptamineUnknownUnknown
Footnotes:a =AMT is a not only apsychedelic but is also astimulant andentactogen.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 psychedelicorally but to be much lesspotent 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
CompoundChemical nameDoseDuration
2-Methyl-DMT2-Methyl-N,N-dimethyltryptamine50–100 mg4–6 hours
2-Methyl-DET2-Methyl-N,N-diethyltryptamine80–120 mg6–8 hours
4-MeO-MiPT4-Methoxy-N-methyl-N-isopropyltryptamines20–30 mg4–6 hours
4,5-MDO-DMT4,5-Methylenedioxy-N,N-dimethyltryptamineUnknownUnknown
4,5-MDO-DiPT4,5-Methylenedioxy-N,N-diisopropyltryptamine>25 mgUnknown
5-Fluoro-DMT5-Fluoro-N,N-dimethyltryptamineUnknownUnknown
5-Bromo-DMT5-Bromo-N,N-dimethyltryptamineUnknownaUnknown
Bretisilocin (5-fluoro-MET)5-Fluoro-N-methyl-N-ethyltryptamineUnknownbUnknownb
5-MeO-2-TMT5-Methoxy-2-methyl-N,N-dimethyltryptamine75–150 mg5–10 hours
5-MeS-DMT5-Methylthio-N,N-dimethyltryptamineUnknowncUnknownc
5,6-MeO-MiPT5,6-Dimethoxy-N-methyl-N-isopropyltryptamine>75 mgUnknown
5,6-MDO-DMT5,6-Methylenedioxy-N,N-dimethyltryptamine>5 mgUnknown
5,6-MDO-DiPT5,6-Methylenedioxy-N,N-diisopropyltryptamineUnknownUnknown
5,6-MDO-MiPT5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine>50–60 mgUnknown
6-Fluoro-DMT6-Fluoro-N,N-dimethyltryptamineUnknownUnknown
6-Fluoro-DET6-Fluoro-N,N-diethyltryptamine>80 mgUnknown
6-HO-DMT6-Hydroxy-N,N-dimethyltryptamine>80 mgUnknown
6-MeO-DiPT6-Methoxy-N,N-diisopropyltryptamine>50 mgUnknown
6-MeO-MiPT6-Methoxy-N-methyl-N-isopropyltryptamine>50 mgUnknown
7-MeO-DiPT7-Methoxy-N,N-diisopropyltryptamine>70 mgUnknown
7-MeO-MiPT7-Methoxy-N-methyl-N-isopropyltryptamine>70 mgUnknown
Footnotes:a5-Bromo-DMT is active viasmoking at a dose of 20 to 50 mg.b =Bretisilocin is activeintravenously with a dose range of 10 to 20 mg and aduration of 60 to 90 minutes.c =5-MeS-DMT's oral dose and duration are unknown, butsmoked 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, andTrip killer § Serotonergic psychedelic antidotes

List of substituted tryptamines

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This list isincomplete; you can help byadding missing items.(October 2021)
StructureNameOriginRing sub.RN1RN2Chemical nameCAS #
Tryptamine (T)Animals, plants, fungiHHH3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine61-54-1
NMTPlantsHHCH3N-methyltryptamine61-49-4
2-HO-NMTPlants2-OHHCH32-hydroxy-N-methyltryptamine106987-89-7
5-MeO-NMTPlants5-OCH3HCH35-methoxy-N-methyltryptamine2009-03-2
Serotonin (5-HT)Animals, plants5-OHHH5-hydroxytryptamine50-67-9
N-Methylserotonin (NMS; norbufotenin; 5-HO-NMT)Plants5-OHHCH35-hydroxy-N-methyltryptamine1134-01-6
Bufotenin (5-HO-DMT)Animals, plants, fungi5-OHCH3CH35-hydroxy-N,N-dimethyltryptamine487-93-4
Bufotenidine (5-HTQ)Amphibians5-O(CH3)33-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate487-91-2
Bufoviridine (5-SO-DMT)Amphibians5-SOCH3CH35-sulfooxy-N,N-dimethyltryptamine16369-08-7
Melatonin (5-MeO-NAcT)Animals, plants, microbes5-OCH3HO=C-CH35-methoxy-N-acetyltryptamine73-31-4
N-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT)Animals5-OHHO=C-CH35-hydroxy-N-acetyltryptamine1210-83-9
6-HydroxymelatoninAnimals5-OCH3, 6-OHHO=C-CH3N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide2208-41-5
4-Hydroxytryptamine (4-HT)Fungi4-OHHH4-hydroxytryptamine570-14-9
4-HO-NMTFungi4-OHHCH34-hydroxy-N-methyltryptamine28363-70-4
Psilocin (4-HO-DMT)Fungi4-OHCH3CH34-hydroxy-N,N-dimethyltryptamine520-53-6
4-HO-TMTFungi4-OHCH3CH34-hydroxy-N,N,N-trimethyltryptammonium262285-41-6
Norbaeocystin (4-PO-T)Fungi4-OPO3H2HH4-phosphoryloxy-tryptamine21420-59-7
Baeocystin (4-PO-NMT)Fungi4-OPO3H2HCH34-phosphoryloxy-N-methyl-tryptamine21420-58-6
Psilocybin (4-PO-DMT)Fungi4-OPO3H2CH3CH34-phosphoryloxy-N,N-dimethyltryptamine520-52-5
Aeruginascin (4-PO-TMT)Fungi4-OPO3H2(CH3)3[3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate114264-95-8
DMTAnimals, plantsHCH3CH3N,N-dimethyltryptamine61-50-7
Lespedamine (1-MeO-DMT)Plants1-OCH3CH3CH31-methoxy-N,N-dimethyltryptamine4335-93-7
5-MeO-DMT (mebufotenin)Animals, plants5-OCH3CH3CH35-methoxy-N,N-dimethyltryptamine1019-45-0
5-Bromo-DMTMarine sponges, invertebrates5-BrCH3CH35-bromo-N,N-dimethyltryptamine17274-65-6
6-BromotryptamineMarine invertebrates6-BrHH6-bromotryptamine96624-18-9
5,6-DibromotryptamineMarine invertebrates5,6-BrHH5,6-dibromotryptamine
5,6-Dibromo-NMTMarine invertebrates5,6-BrHCH35,6-dibromo-N-methyltryptamine
5,6-Dibromo-DMTMarine sponges, invertebrates5,6-BrCH3CH35,6-dibromo-N,N-dimethyltryptamine72853-80-6
Desformylflustrabromine (dFBr)Marine invertebrates2-(α,α-dimethylallyl), 6-BrHCH32-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine474657-72-2
Convolutindole AMarine invertebrates2,4,6-Br, 1,7-OCH3CH3CH31,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine443356-86-3
Acetryptine (5-AT)artificial5-COCH3HH5-Acetyltryptamine3551-18-6
5-BTartificial5-OCH2C6H5HH5-Benzyloxytryptamine20776-45-8
5-CTartificial5-CONH2HH5-Carboxamidotryptamine74885-09-9
5-NOTartificial5-O(CH2)8CH3HH5-Nonyloxytryptamine157798-12-4
2-Methyl-5-hydroxytryptamineartificial2-CH3, 5-OHHH3-(2-aminoethyl)-2-methyl-1H-indol-5-ol78263-90-8
NETartificialHHCH2CH3N-ethyltryptamine61-53-0
NiPTartificialHHCH(CH3)2N-isopropyltryptamine14121-10-9
NcPTartificialHHC3H5N-cyclopropyltryptamine
NsBTartificialHHCH(CH3)CH2CH3N-sec-butyltryptamine
NtBTartificialHHC(CH3)3N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine1344092-44-9
N-Benzyltryptamine (NBnT)artificialHHCH2C6H5N-benzyltryptamine15741-79-4
4-HO-NBnTartificial4-OHHCH2C6H54-hydroxy-N-benzyltryptamine
5-MeO-NBnTartificial5-OCH3HCH2C6H55-methoxy-N-benzyltryptamine25100-31-6
5-MeO-T-NBOMeartificial5-OCH3HCH2C6H4(o-OCH3)5-methoxy-N-(ortho-methoxybenzyl)tryptamine1335331-37-7
5-MT-NB3OMe[33]artificial5-OCH3HCH2C6H4(m-OCH3)5-methoxy-N-(meta-methoxybenzyl)tryptamine1648553-42-7
5-MeO-NBpBrTartificial5-OCH3HCH2C6H4(p-Br)N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine155639-13-7
5-MeO-34MPEMT[34]artificial5-OCH3CH3CH2CH2C6H3(p,m-OCH3)N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
Idalopirdineartificial6-FHCH2C6H4(m-OCH2CF2CF2H)2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine467459-31-0
Z2876442907[35]artificial4-CH3HCH2(C3HNS)-COOCH2CH3ethyl 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]artificial4-OHcis-(CHCH3)CH2(CHCH3)3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol
Pyr-TartificialH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole14008-96-9
4-HO-pyr-Tartificial4-OH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol63097-26-7
Cis-2',5'-dimethyl-4-HO-pyr-T[36]artificial4-OHcis-(CHCH3)CH2CH2(CHCH3)3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol
5-MeO-pyr-Tartificial5-OCH3(CH2)45-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole3949-14-2
4-F-5-MeO-pyr-Tartificial4-F-5-OCH3(CH2)44-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole344790-93-8
IndolylethylfentanylartificialH(CH2)5-4-N(COCH2CH3)C6H5N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide58399-46-5
METartificialHCH3CH2CH3N-Methyl-N-ethyltryptamine5599-69-9
MPTartificialHCH3CH2CH2CH3N-Methyl-N-propyltryptamine850032-72-3
MiPTartificialHCH3CH(CH3)2N-Methyl-N-isopropyltryptamine96096-52-5
McPTartificialHCH3C3H5N-Methyl-N-cyclopropyltryptamine1373918-63-8
EcPTartificialHCH2CH3C3H5N-ethyl-N-cyclopropyltryptamine
PcPTartificialHCH2CH2CH3C3H5N-propyl-N-cyclopropyltryptamine
iPcPTartificialHCH(CH3)2C3H5N-isopropyl-N-cyclopropyltryptamine
DcPTartificialHC3H5C3H5N,N-dicyclopropyltryptamine1373918-62-7
MBTartificialHCH3(CH2)3CH3N-Methyl-N-butyltryptamine848130-12-1
MsBTartificialHCH3CH(CH3)CH2CH3N-Methyl-N-sec-butyltryptamine
MiBTartificialHCH3CH2CH(CH3)2N-Methyl-N-iso-butyltryptamine
McPMTartificialHCH3CH2C3H5N-Methyl-N-(cyclopropylmethyl)tryptamine
DETartificialHCH2CH3CH2CH3N,N-diethyltryptamine61-51-8
EPTartificialHCH2CH3CH2CH2CH3N-Ethyl-N-propyltryptamine850032-68-7
EiPTartificialHCH2CH3CH(CH3)2N-Ethyl-N-isopropyltryptamine848130-11-0
DPTartificialHCH2CH2CH3CH2CH2CH3N,N-dipropyltryptamine61-52-9
PiPTartificialHCH2CH2CH3CH(CH3)2N-Propyl-N-isopropyltryptamine1354632-00-0
DiPTartificialHCH(CH3)2CH(CH3)2N,N-diisopropyltryptamine14780-24-6
EBTartificialHCH2CH3(CH2)3CH3N-ethyl-N-butyltryptamine
PBTartificialHCH2CH2CH3(CH2)3CH3N-propyl-N-butyltryptamine
iPsBTartificialHCH(CH3)2CH(CH3)CH2CH3N-isopropyl-N-sec-butyltryptamine
DBTartificialH(CH2)3CH3(CH2)3CH3N,N-dibutyltryptamine15741-77-2
DiBTartificialHCH2CH(CH3)2CH2CH(CH3)2N,N-diisobutyltryptamine63938-64-7
DsBTartificialHCH(CH3)CH2CH3CH(CH3)CH2CH3N,N-disecbutyltryptamine
MALTartificialHCH3H2C=CH-CH2N-methyl-N-allyltryptamine1366416-29-6
DALTartificialHH2C=CH-CH2H2C=CH-CH2N,N-diallyltryptamine60676-77-9
iPALT (ALiPT)artificialHH2C=CH-CH2CH(CH3)2N-allyl-N-isopropyltryptamine
2-Methyl-DMTartificial2-CH3CH3CH3(2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine1080-95-1
2-Methyl-DETartificial2-CH3CH2CH3CH2CH3N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine26628-88-6
4-Amino-DMT[37]artificial4-NH2CH3CH34-amino-N,N-dimethyltryptamine60331-61-5
4-Methyl-DMTartificial4-CH3CH3CH34,N,N-trimethyltryptamine28289-23-8
4-MeO-DMTartificial4-OCH3CH3CH34-methoxy-N,N-dimethyltryptamine3965-97-7
4-MeO-MiPTartificial4-OCH3CH3CH(CH3)24-methoxy-N-methyl-N-isopropyltryptamine96096-53-6
4-MeO-DiPTartificial4-OCH3CH(CH3)2CH(CH3)24-methoxy-N,N-diisopropyltryptamine
4-AcO-DMTartificial4-OCOCH3CH3CH34-acetoxy-N,N-dimethyltryptamine92292-84-7
4-PrO-DMTartificial4-OCOCH2CH3CH3CH34-propionyloxy-N,N-dimethyltryptamine1373882-11-1
4-GO-DMT (RE109; FT-109)artificial4-OCO(CH2)3COOHCH3CH34-glutaryloxy-N,N-dimethyltryptamine
4-HO-METartificial4-OHCH3CH2CH34-hydroxy-N-methyl-N-ethyltryptamine77872-41-4
4-AcO-METartificial4-OCOCH3CH3CH2CH34-acetoxy-N-methyl-N-ethyltryptamine1445751-40-5
4-PO-METartificial4-OPO3H2CH3CH2CH34-phosphoryloxy-N-methyl-N-ethyltryptamine
4-HO-DETartificial4-OHCH2CH3CH2CH34-hydroxy-N,N-diethyltryptamine22204-89-3
4-AcO-DETartificial4-OCOCH3CH2CH3CH2CH34-acetoxy-N,N-diethyltryptamine1135424-15-5
4-PO-DETartificial4-OPO3H2CH2CH3CH2CH34-phosphoryloxy-N,N-diethyltryptamine60480-02-6
4-HO-EPTartificial4-OHCH2CH3CH2CH2CH34-hydroxy-N-ethyl-N-propyltryptamine2595431-59-5
4-PO-EPTartificial4-OPO3H2CH2CH3CH2CH2CH34-phosphoryloxy-N-ethyl-N-propyltryptamine
4-AcO-EiPTartificial4-OCOCH3CH2CH3CH(CH3)24-acetoxy-N-ethyl-N-isopropyltryptamine
4-HO-MPTartificial4-OHCH3CH2CH2CH34-hydroxy-N-methyl-N-propyltryptamine763035-03-6
4-HO-MiPTartificial4-OHCH(CH3)2CH34-hydroxy-N-isopropyl-N-methyltryptamine77872-43-6
4-AcO-MiPTartificial4-OCOCH3CH3CH(CH3)24-acetoxy-N-methyl-N-isopropyltryptamine1024612-25-6
4-HO-MALT[38]artificial4-OHCH3H2C=CH-CH24-hydroxy-N-Methyl-N-allyltryptamine
4-AcO-MALT[39]artificial4-OCOCH3CH3H2C=CH-CH24-acetoxy-N-Methyl-N-allyltryptamine
4-HO-NALT[40]artificial4-OHHH2C=CH-CH24-hydroxy-N-allyltryptamine
4-HO-MsBTartificial4-OHCH(CH3)CH2CH3CH34-hydroxy-N-sec-butyl-N-methyltryptamine
4-HO-EiBTartificial[41]4-OHCH2CH(CH3)2CH2CH34-hydroxy-N-iso-butyl-N-ethyltryptamine
4-HO-McPTartificial4-OHC3H5CH34-hydroxy-N-cyclopropyl-N-methyltryptamine2883663-05-4
4-HO-McPeTartificial4-OHC5H9CH34-hydroxy-N-cyclopentyl-N-methyltryptamine77872-48-1
4-HO-McPMT[42]artificial4-OHCH2C3H5CH34-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
4-HO-DPTartificial4-OHCH2CH2CH3CH2CH2CH34-hydroxy-N,N-dipropyltryptamine63065-88-3
4-AcO-DPTartificial4-OCOCH3CH2CH2CH3CH2CH2CH34-acetoxy-N,N-dipropyltryptamine1445751-75-6
4-HO-PiPTartificial4-OHCH2CH2CH3CH(CH3)24-hydroxy-N-propyl-N-isopropyltryptamine
4-AcO-PiPTartificial4-OCOCH3CH2CH2CH3CH(CH3)24-acetoxy-N-propyl-N-isopropyltryptamine
4-HO-DiPTartificial4-OHCH(CH3)2CH(CH3)24-hydroxy-N,N-diisopropyltryptamine132328-45-1
4-AcO-DiPTartificial4-OCOCH3CH(CH3)2CH(CH3)24-acetoxy-N,N-diisopropyltryptamine936015-60-0
4-PrO-DiPTartificial4-OCOCH2CH3CH(CH3)2CH(CH3)24-propionyloxy-N,N-diisopropyltryptamine1373882-13-3
Luvesilocin (RE104; FT-104)artificial4-OCO(CH2)3COOHCH(CH3)2CH(CH3)24-glutaryloxy-N,N-diisopropyltryptamine
4-PO-DiPTartificial4-OPO3H2CH(CH3)2CH(CH3)24-phosphoryloxy-N,N-diisopropyltryptamine1373882-09-7
4-HO-DALTartificial4-OHH2C=CH-CH2H2C=CH-CH24-hydroxy-N,N-diallyltryptamine2173386-70-2
4-AcO-DALTartificial4-OCOCH3H2C=CH-CH2H2C=CH-CH24-acetoxy-N,N-diallyltryptamine1445751-71-2
4-HO-DBTartificial4-OH(CH2)3CH3(CH2)3CH34-hydroxy-N,N-dibutyltryptamine63065-89-4
4-HO-DiBTartificial4-OHCH2CH(CH3)2CH2CH(CH3)24-hydroxy-N,N-diisobutyltryptamine
4-HO-DsBTartificial4-OHCH(CH3)CH2CH3CH(CH3)CH2CH34-hydroxy-N,N-disecbutyltryptamine127507-01-1
5-MeO-METartificial5-OCH3CH2CH3CH35-methoxy-N-Methyl-N-ethyltryptamine16977-53-0
5-MeO-DETartificial5-OCH3CH2CH3CH2CH35-methoxy-N,N-diethyltryptamine2454-70-8
5-MeO-MPTartificial5-OCH3CH3CH2CH2CH35-methoxy-N-methyl-N-propyltryptamine
5-MeO-EPTartificial5-OCH3CH2CH3CH2CH2CH35-methoxy-N-ethyl-N-propyltryptamine850032-67-6
5-MeO-DPTartificial5-OCH3CH2CH2CH3CH2CH2CH35-methoxy-N,N-dipropyltryptamine69496-75-9
5-MeO-MALTartificial5-OCH3H2C=CH-CH2CH35-methoxy-N-Methyl-N-allyltryptamine1373918-64-9
5-MeO-DALTartificial5-OCH3H2C=CH-CH2H2C=CH-CH25-methoxy-N,N-diallyltryptamine928822-98-4
ASR-3001 (5-MeO-iPALT)artificial5-OCH3H2C=CH-CH2CH2CH(CH3)25-methoxy-N-allyl-N-isopropyltryptamine
5-MeO-MiPTartificial5-OCH3CH3CH(CH3)25-methoxy-N,N-methylisopropyltryptamine96096-55-8
5,6-MeO-MiPTartificial5-OCH3, 6-OCH3CH3CH(CH3)25,6-dimethoxy-N,N-methylisopropyltryptamine
5-MeO-McPTartificial5-OCH3CH3C3H55-methoxy-N-methyl-N-cyclopropyltryptamine
5-MeO-McBTartificial5-OCH3CH3C4H75-methoxy-N-methyl-N-cyclobutyltryptamine
5-MeO-EiPTartificial5-OCH3CH2CH3CH(CH3)25-methoxy-N-ethyl-N-isopropyltryptamine850032-66-5
5-MeO-PiPTartificial5-OCH3CH2CH2CH3CH(CH3)25-methoxy-N-propyl-N-isopropyltryptamine
5-MeO-DiPTartificial5-OCH3CH(CH3)2CH(CH3)25-methoxy-N,N-diisopropyltryptamine4021-34-5
5-MeO-DBTartificial5-OCH3(CH2)3CH3(CH2)3CH35-methoxy-N,N-dibutyltryptamine73785-42-9
5-MeO-DsBTartificial5-OCH3CH(CH3)CH2CH3CH(CH3)CH2CH35-methoxy-N,N-di-sec-butyltryptamine
5-MeS-DMTartificial5-SCH3CH3CH35-methylthio-N,N-dimethyltryptamine5102-11-4
5-AcO-DMTartificial5-OCOCH3CH3CH35-acetoxy-N,N-dimethyltryptamine16977-50-7
5-AcO-MET[43]artificial5-OCOCH3CH3CH2CH35-acetoxy-N-methyl-N-ethyltryptamine
5-AcO-DETartificial5-OCOCH3CH2CH3CH2CH35-acetoxy-N,N-diethyltryptamine
5-AcO-EPT[44]artificial5-OCOCH3CH2CH3CH2CH2CH35-acetoxy-N-ethyl-N-propyltryptamine
5-AcO-DPTartificial5-OCOCH3CH2CH2CH3CH2CH2CH35-acetoxy-N,N-dipropyltryptamine
5-AcO-MiPTartificial5-OCOCH3CH3CH(CH3)25-acetoxy-N-methyl-N-isopropyltryptamine
5-AcO-DiPTartificial5-OCOCH3CH(CH3)2CH(CH3)25-acetoxy-N,N-diisopropyltryptamine
5-Ethoxy-DMTartificial5-OCH2CH3CH3CH35-ethoxy-N,N-dimethyltryptamine855245-09-9
5-Ethoxy-METartificial5-OCH2CH3CH3CH2CH35-ethoxy-N-methyl-N-ethyltryptamine
5-Ethoxy-DETartificial5-OCH2CH3CH2CH3CH2CH35-ethoxy-N,N-diethyltryptamine
5-Ethoxy-MPTartificial5-OCH2CH3CH3CH2CH2CH35-ethoxy-N-methyl-N-propyltryptamine
5-Ethoxy-EPTartificial5-OCH2CH3CH2CH3CH2CH2CH35-ethoxy-N-ethyl-N-propyltryptamine
5-Ethoxy-DPTartificial5-OCH2CH3CH2CH2CH3CH2CH35-ethoxy-N,N-dipropyltryptamine
5-Ethoxy-MiPTartificial5-OCH2CH3CH3CH(CH3)25-ethoxy-N-methyl-N-isopropyltryptamine
5-Ethoxy-EiPTartificial5-OCH2CH3CH2CH3CH(CH3)25-ethoxy-N-ethyl-N-isopropyltryptamine
5-Ethoxy-DiPTartificial5-OCH2CH3CH(CH3)2CH(CH3)25-ethoxy-N,N-diisopropyltryptamine
5-Ethoxy-DALTartificial5-OCH2CH3H2C=CH-CH2H2C=CH-CH25-ethoxy-N,N-diallyltryptamine
5-BnO-DMTartificial5-OCH2C6H5CH3CH35-benzyloxy-N,N-dimethyltryptamine101832-88-6
5-HO-DETartificial5-OHCH2CH3CH2CH35-hydroxy-N,N-diethyltryptamine14009-42-8
5-HO-DPTartificial5-OHCH2CH2CH3CH2CH2CH35-hydroxy-N,N-dipropyltryptamine36288-75-2
5-HO-MiPTartificial5-OHCH3CH(CH3)25-hydroxy-N-methyl-N-isopropyltryptamine
5-HO-DiPTartificial5-OHCH(CH3)2CH(CH3)25-hydroxy-N,N-diisopropyltryptamine36288-76-3
5-Methyl-DMT (5,N,N-TMT)artificial5-CH3CH3CH35,N,N-trimethyltryptamine22120-39-4
5-Ethyl-DMTartificial5-CH2CH3CH3CH35-ethyl-N,N-dimethyltryptamine171783-25-8
5-Isopropyl-DMTartificial5-CH(CH3)2CH3CH35-isopropyl-N,N-dimethyltryptamine156281-04-8
5-(t-Butyl)-DMT[45]artificial5-C(CH3)3CH3CH35-(tert-butyl)-N,N-dimethyltryptamine
5-Fluoro-DMTartificial5-FCH3CH35-fluoro-N,N-dimethyltryptamine22120-36-1
Bretisilocin (5-fluoro-MET; GM-2505)artificial5-FCH3CH2CH35-fluoro-N-methyl-N-ethyltryptamine2698331-35-8
5-Fluoro-DETartificial5-FCH2CH3CH2CH35-fluoro-N,N-diethyltryptamine
5-Fluoro-EPTartificial5-FCH2CH3CH2CH2CH35-fluoro-N-ethyl-N-propyltryptamine
5-Fluoro-DPTartificial5-FCH2CH2CH3CH2CH2CH35-fluoro-N,N-dipropyltryptamine
5-Fluoro-PiPTartificial5-FCH2CH2CH3CH(CH3)25-fluoro-N-propyl-N-isopropyltryptamine
5-Fluoro-PcBTartificial5-FCH2CH2CH3CH(CH2)35-fluoro-N-propyl-N-cyclobutyltryptamine
5-Fluoro-iPcBTartificial5-FCH(CH3)2CH(CH2)35-fluoro-N-isopropyl-N-cyclobutyltryptamine
5-Fluoro-DiPTartificial5-FCH(CH3)2CH(CH3)25-fluoro-N,N-diisoproptryptamine
5-Fluoro-sBALTartificial5-FCH(CH3)CH2CH3CH2CH=CH25-fluoro-N-sec-butyl-N-allyltryptamine
5-Fluoro-M1MALTartificial5-FCH3CH(CH3)CH=CH25-fluoro-N-methyl-N-(1-methylallyl)tryptamine
5-Chloro-DMTartificial5-ClCH3CH35-chloro-N,N-dimethyltryptamine22120-32-7
5-Iodo-DMTartificial5-ICH3CH35-iodo-N,N-dimethyltryptamine22120-38-3
5-TFM-DMTartificial5-CF3CH3CH35-(trifluoromethyl)-N,N-dimethyltryptamine2418713-32-1
5-TFMO-DMT[46]artificial5-OCF3CH3CH35-(trifluoromethoxy)-N,N-dimethyltryptamine
5-Nitro-DMT[47]artificial5-NO2CH3CH35-nitro-N,N-dimethyltryptamine69937-13-9
5-CN-DMTartificial5-C≡NCH3CH35-cyano-N,N-dimethyltryptamine17380-42-6
5-CN-DPTartificial5-C≡NCH2CH2CH3CH2CH2CH35-cyano-N,N-dipropyltryptamine74885-19-1
Almotriptanartificial5-(CH2SO2N(CH2)4)CH3CH3N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine154323-57-6
Rizatriptanartificial5-(CH2(N3(CH)2))CH3CH3N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine145202-66-0
Sumatriptanartificial5-(CH2SO2NHCH3)CH3CH31-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide103628-46-2
Zolmitriptanartificial5-(CHNHC=OOCH2)CH3CH35-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine139264-17-8
6-Fluoro-DMTartificial6-FCH3CH36-fluoro-N,N-dimethyltryptamine1511-31-5
6-Fluoro-DET[48]artificial6-FCH2CH3CH2CH36-fluoro-N,N-diethyltryptamine2836-69-3
6-Chloro-DMTartificial6-ClCH3CH36-chloro-N,N-dimethyltryptamine25390-72-1
6-Methyl-DMTartificial6-CH3CH3CH36,N,N-trimethyltryptamine
6-Hydroxy-DMTartificial6-OHCH3CH36-hydroxy-N,N-dimethyltryptamine1476-33-1
6-Hydroxy-DETartificial6-OHCH3CH36-hydroxy-N,N-diethyltryptamine1476-59-1
6-Methoxy-DMTartificial6-OCH3CH3CH36-methoxy-N,N-dimethyltryptamine2426-88-2
7-Methyl-DMTartificial7-CH3CH3CH37,N,N-trimethyltryptamine65882-39-5
7-Ethyl-DMTartificial7-CH2CH3CH3CH37-ethyl-N,N-dimethyltryptamine
7-Chloro-DMTartificial7-ClCH3CH37-chloro-N,N-dimethyltryptamine
7-Bromo-DMT[49]artificial7-BrCH3CH37-bromo-N,N-dimethyltryptamine74798-68-8
7-Methoxy-DMTartificial7-OCH3CH3CH37-methoxy-N,N-dimethyltryptamine
7-Methoxy-MiPTartificial7-OCH3CH3CH(CH3)27-methoxy-N-methyl-N-isopropyltryptamine
1-Methylpsilocinartificial1-CH3, 4-OHCH3CH31-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole1465-16-3
1-Methyl-5-MeO-DiPTartificial1-CH3, 5-OCH3CH(CH3)2CH(CH3)21-methyl-5-methoxy-N,N-diisopropyltryptamine1373882-10-0
NBoc-DMTartificial1-OCOC(CH3)3CH3CH31-(t-butoxycarbonyl)-N,N-dimethyltryptamine
NB-5-MeO-MiPTartificial1-OCOC(CH3)3, 5-OCH3CH3CH(CH3)21-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
NB-5-MeO-DALTartificial1-OCOC(CH3)3, 5-OCH3H2C=CH-CH2H2C=CH-CH21-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine
6-Fluoropsilocinartificial4-OH,6-FCH3CH34-hydroxy-6-fluoro-N,N-dimethyltryptamine312314-12-8
6-Fluoro-5-MeO-DMTartificial5-OCH3,6-FCH3CH35-methoxy-6-fluoro-N,N-dimethyltryptamine
5,6-Difluoro-EPTartificial5-F, 6-FCH2CH3CH2CH2CH35,6-difluoro-N-ethyl-N-propyltryptamine
5-MeO-2-TMTartificial2-CH3, 5-OCH3CH3CH32-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine67292-68-6
5-MeO-7-TMTartificial5-OCH3, 7-CH3CH3CH35-Methoxy-7,N,N-trimethyltryptamine61018-77-7
5-MeO-4-TMTartificial4-CH3, 5-OCH3CH3CH35-Methoxy-4,N,N-trimethyltryptamine
4-HO-5-MeO-DMT (psilomethoxin)artificial4-OH, 5-OCH3CH3CH34-Hydroxy-5-methoxy-N,N-dimethyltryptamine2433-31-0
4-F-5-MeO-DMTartificial4-F, 5-OCH3CH3CH34-Fluoro-5-Methoxy-N,N-dimethyltryptamine312314-18-4
5-MeO-7-F-METartificial5-OCH3, 7-FCH3CH2CH35-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
EMDT (2-ethyl-5-MeO-DMT)artificial2-CH2CH3, 5-OCH3CH3CH32-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine263744-72-5
ST-1936 (2-methyl-5-chloro-DMT)artificial2-CH3, 5-ClCH3CH32-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine1210-81-7
O-4310 (1-isopropyl-6-fluoropsilocin)artificial1-CH(CH3)2, 4-OH, 6-FCH3CH33-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol885671-63-6
CP-132,484 (4,5-DHP-1-Me-T)artificial1-methyl-4,5-(OCH2CH2CH2)HH1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole143508-76-3
4,5-DHP-DMTartificial4,5-(OCH2CH2CH2)CH3CH31-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole135360-97-3
4,5-DHF-DMT (P-3)artificial[50]4,5-(CH2CH2O)CH3CH32-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
4,5-Methylbenzoxazole-DMT (P-131)artificial4,5-(OC(CH3)=N)CH3CH3N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine
4,5-MDO-DMTartificial4,5-(OCH2O)CH3CH32-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine81249-30-1
4,5-MDO-DiPTartificial4,5-(OCH2O)CH(CH3)2CH(CH3)2N-[2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine82173-82-8
5,6-FUR-DMT (P-4)artificial5,6-(CH=CHO)CH3CH32-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine
5,6-MDO-DMTartificial5,6-(OCH2O)CH3CH32-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine
5,6-MDO-MiPTartificial5,6-(OCH2O)CH3CH(CH3)2N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine
5,6-MDO-DiPTartificial5,6-(OCH2O)CH(CH3)2CH(CH3)2N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine
StructureShort NameOriginRing SubstitutionRN1RN2Full NameCAS #

List of substituted α-alkyltryptamines

[edit]

α-Alkyltryptamines are a group of substituted tryptamines which possess analkyl group, such as amethyl orethyl group, attached at thealpha carbon, and in most cases no substitution on theamine nitrogen.[51][52][53] α-Alkylation oftryptamine makes it much moremetabolically stable and resistant to degradation bymonoamine oxidase, resulting in increasedpotency and greatly lengthenedhalf-life.[53] This is analogous to α-methylation ofphenethylamine intoamphetamine.[53]

Many α-alkyltryptamines aredrugs, acting asmonoamine releasing agents, non-selectiveserotonin receptor agonists, and/ormonoamine oxidase inhibitors,[54][55][56][57] and producepsychostimulant,entactogen, and/orpsychedelic effects.[51][52][53] The most well-known of these agents areα-methyltryptamine (αMT) andα-ethyltryptamine (αET), both of which were used clinically asantidepressants for a brief period of time in the past and areabused asrecreational drugs.[52][53] In accordance with its action as a dualreleasing agent ofserotonin anddopamine, αET has been found to produceserotonergicneurotoxicity similarly toamphetamines likeMDMA andPCA, 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]

StructureNameChemical nameCAS #
Tryptophan(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid73-22-3
5-Hydroxytryptophan (5-HTP)2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid4350-09-8
αMT (AMT; Indopan)1-(1H-Indol-3-yl)propan-2-amine299-26-3
4-HO-αMT3-(2-aminopropyl)-1H-indol-4-ol15066-09-8
4-Methyl-αMT1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine3569-29-7
5-Fluoro-αMT1-(5-fluoro-1H-indol-3-yl)propan-2-amine712-08-3
5-Chloro-αMT1-(5-Chloro-1H-indol-3-yl)propan-2-amine712-07-2
5-HO-αMT (αMS/α-methyl-5-HT)3-(2-aminopropyl)-1H-indol-5-ol304-52-9
5-MeO-αMT1-(5-methoxy-1H-indol-3-yl)propan-2-amine1137-04-8
5-Ethoxy-αMT1-(5-ethoxy-1H-indol-3-yl)propan-2-amine101832-83-1
5-Isopropoxy-αMT1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine
5-Allyloxy-αMT1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine
BW-723C861-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine160521-72-2
6-Fluoro-αMT1-(6-fluoro-1H-indol-3-yl)propan-2-amine712-11-8
7-Chloro-AMT1-(7-chloro-1H-indol-3-yl)propan-2-amine711-99-9
AL-37350A (4,5-DHP-αMT)(S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole362603-40-5
Compound 5[59]1-(3H-benzo[e]indol-1-yl)propan-2-amine
αET1-(1H-indol-3-yl)butan-2-amine2235-90-7
4-Methyl-αET1-(4-Methyl-1H-indol-3-yl)butan-2-amine28289-30-7
4-HO-αET1-(4-hydroxy-1H-indol-3-yl)butan-2-amine28289-28-3
5-Fluoro-αET1-(5-fluoro-1H-indol-3-yl)butan-2-amine1380137-98-3
5-Methyl-αET1-(5-methyl-1H-indol-3-yl)butan-2-amine1380148-21-9
5-MeO-αET1-(5-methoxy-1H-indol-3-yl)butan-2-amine4765-10-0
7-Methyl-αET1-(7-methyl-1H-indol-3-yl)butan-2-amine13712-80-6
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)amine4822-13-3
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)dimethylamine4761-32-4
N,N-Dimethyl-5-MeO-αMT (5-MeO-α,N,N-TMT)(2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine101831-90-7
α-Methyl-DiPT(2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
MPMI[60]3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143321-54-4
Lucigenol (4-HO-MPMI)(R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole250672-65-2
5-MeO-MPMI (CP-108509)5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole143321-57-7
5F-MPMI[61](R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole
5-Br-MPMI5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143322-57-0
Eletriptan3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole143322-58-1
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 ofβ-ketotryptamines (beta-ketotryptamines) are known.[63][65][68] These compounds are α-alkyl-β-ketotryptamines and are analogous to thecathinones (β-ketoamphetamines) of the relatedphenethylamine family. Known β-ketotryptamines includeBK-NM-AMT,BK-5F-NM-AMT,BK-5Cl-NM-AMT, andBK-5Br-NM-AMT.[63][65][68] They act asmonoamine releasing agents.[63][65][68]

Cyclized tryptamines

[edit]

Examples ofcyclized tryptamines include:

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

Related compounds

[edit]

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

StructureNameChemical nameCAS #
C-DMT[73]2-(3H-inden-1-yl)-N,N-dimethylethanamine
Dimemebfe (5-MeO-BFE)2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine140853-58-3
5-MeO-DiBFN-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
3-APB3-(2-aminopropyl)benzofuran105909-13-5
3-APBT (SKF-6678)1-(1-benzothiophen-3-yl)propan-2-amine1201-27-0
Mebfap (5-MeO-3-APB)3-(2-aminopropyl)-5-methoxybenzofuran140853-59-4
Isotryptamine (isoT)2-indol-1-ylethanamine13708-58-2
isoAMT1-indol-1-ylpropan-2-amine1227465-67-9
(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-amine169675-09-6
isoDMT2-indol-1-yl-N,N-dimethylethanamine87482-09-5
5-MeO-isoDMT2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine244122-80-3
6-MeO-isoDMT2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine87482-11-9
Zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-Me-isoDMT)(2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine2481740-94-5
2ZEDMA2-indolizin-1-yl-N,N-dimethylethanamine
1ZP2MA1-indolizin-1-yl-N-methylpropan-2-amine
1Z2MAP1O1-indolizin-3-yl-2-(methylamino)propan-1-one2110204-31-2
Example 16[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-amine259857-99-3
AL-34662 (indazole-5-HO-AMT)1-((S)-2-Aminopropyl)-1H-indazol-6-ol210580-75-9
O-Methyl-AL-34662 (indazole-5-MeO-AMT)1-((S)-6-methoxy-2-aminopropyl)-1H-indazole210580-60-2
7-Methyl-AL-346621-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol874668-67-4
7-Chloro-AL-346621-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol874881-86-4
AL-38022A(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine478132-11-5
Example 9[78](S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine478132-12-6
Example 3[79](S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine890087-75-9
Example 1[80](S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine1373917-69-1
YM-348(2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine372163-84-3
2-Desethyl-YM-348[81](2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine748116-94-1
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-indole2945139-94-4
RU-28253 (5-MeO-THPI)5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole
NEtPhOH-THPI (compound 24c)3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole
VU6067416[84]3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole3027515-24-5
(R)-693-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine2765652-48-8
SN-223-(1-methylpiperidin-4-yl)-1H-indole17403-07-5
RU-24,9695-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole107008-28-6
EMD-3860885-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole54635-62-0

Overview table

[edit]
Simple tryptamines and their common derivatives
Simple4-Hydroxy4-Acetoxy5-Methoxy5-Hydroxy
Tryptamine (T)4-HO-T (dinorpsilocin)4-AcO-T5-MeO-T (O-methylserotonin)5-HO-T (serotonin; 5-HT)
NAcT4-HO-NAcT4-AcO-NAcT5-MeO-NAcT (melatonin)5-HO-NAcT (normelatonin; NAS)
NMT4-HO-NMT (norpsilocin)4-AcO-NMT5-MeO-NMT5-HO-NMT (N-methylserotonin)
NET4-HO-NET4-AcO-NET5-MeO-NET5-HO-NET
NPT4-HO-NPT4-AcO-NPT5-MeO-NPT5-HO-NPT
NiPT4-HO-NiPT4-AcO-NiPT5-MeO-NiPT5-HO-NiPT
NALT4-HO-NALT4-AcO-NALT5-MeO-NALT5-HO-NALT
NBT4-HO-NBT4-AcO-NBT5-MeO-NBT5-HO-NBT
NiBT4-HO-NiBT4-AcO-NiBT5-MeO-NiBT5-HO-NiBT
NsBT4-HO-NsBT4-AcO-NsBT5-MeO-NsBT5-HO-NsBT
NtBT4-HO-NtBT4-AcO-NtBT5-MeO-NtBT5-HO-NtBT
NAT4-HO-NAT4-AcO-NAT5-MeO-NAT5-HO-NAT
NHT4-HO-NHT4-AcO-NHT5-MeO-NHT5-HO-NHT
NcPT4-HO-NcPT4-AcO-NcPT5-MeO-NcPT5-HO-NcPT
NBnT4-HO-NBnT4-AcO-NBnT5-MeO-NBnT5-HO-NBnT
NBOMeT4-HO-NBOMeT4-AcO-NBOMeT5-MeO-NBOMeT5-HO-NBOMeT
NB3OMeT4-HO-NB3OMeT4-AcO-NB3OMeT5-MeO-NB3OMeT5-HO-NB3OMeT
DMT4-HO-DMT (psilocin)4-AcO-DMT (psilacetin)5-MeO-DMT (mebufotenin)5-HO-DMT (bufotenin)
DET4-HO-DET (ethocin)4-AcO-DET (ethacetin)5-MeO-DET5-HO-DET
DPT4-HO-DPT (deprocin)4-AcO-DPT (depracetin)5-MeO-DPT5-HO-DPT (DiPS, NDPS)
DiPT4-HO-DiPT (iprocin)4-AcO-DiPT (ipracetin)5-MeO-DiPT (foxy)5-HO-DiPT
DALT4-HO-DALT (daltocin)4-AcO-DALT (dalcetin)5-MeO-DALT (foxtrot)5-HO-DALT
DBT4-HO-DBT4-AcO-DBT5-MeO-DBT5-HO-DBT
DiBT4-HO-DiBT4-AcO-DiBT5-MeO-DiBT5-HO-DiBT
DsBT4-HO-DsBT4-AcO-DsBT5-MeO-DsBT5-HO-DsBT
DtBT4-HO-DtBT4-AcO-DtBT5-MeO-DtBT5-HO-DtBT
DAT4-HO-DAT4-AcO-DAT5-MeO-DAT5-HO-DAT
DHT4-HO-DHT4-AcO-DHT5-MeO-DHT5-HO-DHT
DcPT4-HO-DcPT4-AcO-DcPT5-MeO-DcPT5-HO-DcPT
MET4-HO-MET (metocin)4-AcO-MET (metacetin)5-MeO-MET5-HO-MET
MPT4-HO-MPT (meprocin)4-AcO-MPT5-MeO-MPT5-HO-MPT
MiPT4-HO-MiPT (miprocin)4-AcO-MiPT (mipracetin)5-MeO-MiPT (moxy)5-HO-MiPT
MALT4-HO-MALT (maltocin)4-AcO-MALT5-MeO-MALT5-HO-MALT
MBT4-HO-MBT4-AcO-MBT5-MeO-MBT5-HO-MBT
MiBT4-HO-MiBT4-AcO-MiBT5-MeO-MiBT5-HO-MiBT
MsBT4-HO-MsBT4-AcO-MsBT5-MeO-MsBT5-HO-MsBT
MtBT4-HO-MtBT4-AcO-MtBT5-MeO-MtBT5-HO-MtBT
McPT4-HO-McPT4-AcO-McPT5-MeO-McPT5-HO-McPT
McPMT4-HO-McPMT4-AcO-McPMT5-MeO-McPMT5-HO-McPMT
McPeT4-HO-McPeT4-AcO-McPeT5-MeO-McPeT5-HO-McPeT
EPT4-HO-EPT (eprocin)4-AcO-EPT5-MeO-EPT5-HO-EPT
EiPT4-HO-EiPT (eiprocin)4-AcO-EiPT5-MeO-EiPT5-HO-EiPT
EALT4-HO-EALT4-AcO-EALT5-MeO-EALT5-HO-EALT
EBT4-HO-EBT4-AcO-EBT5-MeO-EBT5-HO-EBT
EiBT4-HO-EiBT (eibucin)4-AcO-EiBT5-MeO-EiBT5-HO-EiBT
EsBT4-HO-EsBT4-AcO-EsBT5-MeO-EsBT5-HO-EsBT
EtBT4-HO-EtBT4-AcO-EtBT5-MeO-EtBT5-HO-EtBT
EcPT4-HO-EcPT4-AcO-EcPT5-MeO-EcPT5-HO-EcPT
PiPT4-HO-PiPT (piprocin)4-AcO-PiPT5-MeO-PiPT5-HO-PiPT
PALT4-HO-PALT4-AcO-PALT5-MeO-PALT5-HO-PALT
PBT4-HO-PBT4-AcO-PBT5-MeO-PBT5-HO-PBT
PiBT4-HO-PiBT4-AcO-PiBT5-MeO-PiBT5-HO-PiBT
PsBT4-HO-PsBT4-AcO-PsBT5-MeO-PsBT5-HO-PsBT
PtBT4-HO-PtBT4-AcO-PtBT5-MeO-PtBT5-HO-PtBT
PcPT4-HO-PcPT4-AcO-PcPT5-MeO-PcPT5-HO-PcPT
iPALT (ALiPT)4-HO-iPALT4-AcO-iPALT5-MeO-iPALT (ASR-3001)5-HO-iPALT
iPBT4-HO-iPBT4-AcO-iPBT5-MeO-iPBT5-HO-iPBT
iPiBT4-HO-iPiBT4-AcO-iPiBT5-MeO-iPiBT5-HO-iPiBT
iPsBT4-HO-iPsBT4-AcO-iPsBT5-MeO-iPsBT5-HO-iPsBT
iPtBT4-HO-iPtBT4-AcO-iPtBT5-MeO-iPtBT5-HO-iPtBT
iPcPT4-HO-iPcPT4-AcO-iPcPT5-MeO-iPcPT5-HO-iPcPT
TMT4-HO-TMT4-AcO-TMT5-MeO-TMT5-HO-TMT
Pyr-T4-HO-pyr-T4-AcO-pyr-T5-MeO-pyr-T5-HO-pyr-T
Pip-T4-HO-pip-T4-AcO-pip-T5-MeO-pip-T5-HO-pip-T
MPMI4-HO-MPMI (lucigenol)4-AcO-MPMI5-MeO-MPMI (CP-108509)5-HO-MPMI
THPI4-HO-THPI4-AcO-THPI5-MeO-THPI (RU-28253)5-HO-THPI
Notes: (1) Other notableacyloxy derivatives of the above include4-PrO-DMT,4-PrO-DiPT,4-PrO-MET,4-GO-DMT, and4-GO-DiPT (luvesilocin). (2)4-Phosphoroxy derivatives of the above includenorbaeocystin (4-PO-T),baeocystin (4-PO-NMT),psilocybin (4-PO-DMT),ethocybin (4-PO-DET),4-PO-DiPT,4-PO-MET, andaeruginascin (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, and5-HO-AMT (α-methylserotonin);NMT:α,N-DMT andα,N,O-TMS;NPT:IPAP (α,N-DPT);DMT:α,N,N-TMT andα,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. Retrieved2022-12-26.
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  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.
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  15. ^abcHolze 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. ^abOtt 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.
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  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. Retrieved21 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. Retrieved20 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 fromthe original on 17 April 2016. Retrieved8 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 ofN-methyl-AMT, which is active, or AMT itself maybe. [...]
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Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
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