Substituted tryptamine

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The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN1=RN2=Ra = H. Tryptamine rests General Formula V.svg
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. Tryptamine structure.svg
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, 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.

Contents

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: LSD, ibogaine, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.

List of substituted tryptamines

Selected tryptamines
Chemical structureShort NameOriginRing SubstitutionRN1RN2Full NameCAS Number
Tryptamine structure.svg Tryptamine Animals, plants, fungiHHH3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine61-54-1
NMT structure.svg NMT PlantsHHCH3N-methyltryptamine61-49-4
2-Hydroxy-NMT.svg 2-HO-NMT Plants2-OHHCH32-hydroxy-N-methyltryptamine106987-89-7
5-MeO-NMT.svg 5-MeO-NMT Plants5-OCH3HCH35-methoxy-N-methyltryptamine2009-03-2
Serotonin-2D-skeletal.svg Serotonin Animals, plants5-OHHH5-hydroxytryptamine50-67-9
Norbufotenine.svg Nω-Methylserotonin (norbufotenin)Plants5-OHHCH35-hydroxy-N-methyltryptamine1134-01-6
Bufotenin2DACS.svg Bufotenin Animals, plants, fungi5-OHCH3CH35-hydroxy-N,N-dimethyltryptamine487-93-4
Bufotenidine.png Bufotenidine Amphibians5-O(CH3)33-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate487-91-2
Melatonin.svg Melatonin Animals, plants, microbes5-OCH3 H O=C-CH3 5-methoxy-N-acetyltryptamine73-31-4
N-Acetylserotonin.png N-Acetylserotonin Animals5-OHHO=C-CH35-hydroxy-N-acetyltryptamine1210-83-9
6-Hydroxymelatonin structure.svg 6-Hydroxymelatonin Animals5-OCH3, 6-OHHO=C-CH3N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide2208-41-5
Norpsilocin.svg 4-HO-NMT Fungi4-OH HCH34-hydroxy-N-methyltryptamine28363-70-4
Psilocin.svg Psilocin Fungi4-OH CH3CH34-hydroxy-N,N-dimethyltryptamine520-53-6
Norbaeocystin.svg Norbaeocystin Fungi4-OPO3H2HH4-phosphoryloxy-tryptamine21420-59-7
Baeocystin Formula V.1.svg Baeocystin Fungi4-OPO3H2HCH34-phosphoryloxy-N-methyl-tryptamine21420-58-6
Psilocybin, Kekule, skeletal formula of canonical psilocybin.svg Psilocybin Fungi4-OPO3H2CH3CH34-phosphoryloxy-N,N-dimethyltryptamine520-52-5
Aeruginascin.png Aeruginascin Fungi4-OPO3H2(CH3)3[3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate114264-95-8
DMT.svg DMT Animals, plantsH CH3 CH3N,N-dimethyltryptamine61-50-7
Lespedamine.svg Lespedamine Plants1-OCH3CH3CH31-methoxy-N,N-dimethyltryptamine4335-93-7
5-MeO-DMT.svg 5-MeO-DMT Animals, plants5-OCH3CH3CH35-methoxy-N,N-dimethyltryptamine1019-45-0
5-Bromo-DMT.svg 5-Bromo-DMT Marine sponges, invertebrates5-BrCH3CH35-bromo-N,N-dimethyltryptamine17274-65-6
6-Br-T.svg 6-Bromotryptamine Marine invertebrates6-BrHH6-bromotryptamine96624-18-9
5,6 diBr-T.svg 5,6-Dibromotryptamine Marine invertebrates5,6-BrHH5,6-dibromotryptamine
5,6 diBr-NMT.svg 5,6-Dibromo-NMT Marine invertebrates5,6-BrHCH35,6-dibromo-N-methyltryptamine
5,6-dibromo-DMT.svg 5,6-Dibromo-DMT Marine sponges, invertebrates5,6-BrCH3CH35,6-dibromo-N,N-dimethyltryptamine72853-80-6
Desformylflustrabromine.svg Desformylflustrabromine 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 A.svg Convolutindole A Marine invertebrates2,4,6-Br, 1,7-OCH3CH3CH31,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine443356-86-3
Acetryptine.svg Acetryptine artificial5-COCH3HH5-Acetyltryptamine3551-18-6
5-benzyloxytryptamine.png 5-BT artificial5-OCH2C6H5HH5-Benzyloxytryptamine20776-45-8
5-Carboxamidotryptamine.svg 5-CT artificial5-CONH2HH5-Carboxamidotryptamine74885-09-9
5-Nonyloxytryptamine.svg 5-(Nonyloxy)tryptamine artificial5-O(CH2)8CH3HH5-nonyloxytryptamine157798-12-4
2-Methyl-5-hydroxytryptamine.svg 2-Methyl-5-hydroxytryptamine artificial2-CH3, 5-OHHH3-(2-aminoethyl)-2-methyl-1H-indol-5-ol78263-90-8
N-Ethyltryptamine.png NET artificialHHCH2CH3N-ethyltryptamine61-53-0
NiPT structure.png NiPTartificialHHCH(CH3)2N-isopropyltryptamine14121-10-9
NcPT structure.png NcPTartificialHHC3H5N-cyclopropyltryptamine
NSBT structure.png NSBTartificialHHCH(CH3)CH2CH3N-sec-butyltryptamine
N-t-butyltryptamine.svg NTBT artificialHHC(CH3)3N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine
5MT-NBOMe structure.png 5-MeO-T-NBOMe artificial5-OCH3HCH2C6H4(o-OCH3)5-methoxy-N-(ortho-methoxybenzyl)tryptamine1335331-37-7
5MT-NB3OMe structure.png 5-MT-NB3OMe [2] artificial5-OCH3HCH2C6H4(m-OCH3)5-methoxy-N-(meta-methoxybenzyl)tryptamine1648553-42-7
5-Methoxy-N-(4-bromobenzyl)tryptamine).svg 5-MeO-NBpBrT artificial5-OCH3HCH2C6H4(p-Br)N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine155639-13-7
5-MeO-34MPEMT structure.png 5-MeO-34MPEMT [3] artificial5-OCH3CH3CH2CH2C6H3(p,m-OCH3)N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
Lu-AE58054.svg Idalopirdine artificial6-FHCH2C6H4(m-OCH2CF2CF2H)2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoropropoxy)benzyl)ethanamine467459-31-0
Z2876442907 structure.png Z2876442907 [4] artificial4-CH3HCH2(C3HNS)COOCH2CH3ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate
Pyr-T.png Pyr-T artificialH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole14008-96-9
4-HO-pyr-T.png 4-HO-pyr-T artificial4-OH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol63097-26-7
5-MeO-pyr-T.png 5-MeO-pyr-T artificial5-OCH3(CH2)45-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole3949-14-2
Indolylethylfentanyl structure.png IndolylethylfentanylartificialH(CH2)5-4-N(COCH2CH3)C6H5N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide58399-46-5
MET image.svg MET artificialHCH3CH2CH3N-Methyl-N-ethyltryptamine5599-69-9
MPT structure.png MPTartificialHCH3CH2CH2CH3N-Methyl-N-propyltryptamine850032-72-3
MIPT.svg MiPT artificialHCH3CH(CH3)2N-Methyl-N-isopropyltryptamine96096-52-5
McPT structure.png McPTartificialHCH3C3H5N-Methyl-N-cyclopropyltryptamine1373918-63-8
EcPT structure.png EcPTartificialHCH2CH3C3H5N-ethyl-N-cyclopropyltryptamine
PcPT structure.png PcPTartificialHCH2CH2CH3C3H5N-propyl-N-cyclopropyltryptamine
IPcPT structure.png iPcPTartificialHCH(CH3)2C3H5N-isopropyl-N-cyclopropyltryptamine
DcPT structure.png DcPTartificialHC3H5C3H5N,N-dicyclopropyltryptamine1373918-62-7
Methylbutyltryptamine.svg MBT artificialHCH3(CH2)3CH3N-Methyl-N-butyltryptamine848130-12-1
MSBT structure.png MSBTartificialHCH3CH(CH3)CH2CH3N-Methyl-N-sec-butyltryptamine
MiBT structure.png MiBTartificialHCH3CH2CH(CH3)2N-Methyl-N-iso-butyltryptamine
McPMT structure.png McPMTartificialHCH3CH2C3H5N-Methyl-N-(cyclopropylmethyl)tryptamine
Diethyltryptamine.svg DET artificialHCH2CH3CH2CH3N,N-diethyltryptamine61-51-8
Ethylpropyltryptamine.svg EPT artificialHCH2CH3CH2CH2CH3N-Ethyl-N-propyltryptamine850032-68-7
Ethylisopropyltryptamine.svg EiPT artificialHCH2CH3CH(CH3)2N-Ethyl-N-isopropyltryptamine848130-11-0
DPT.svg DPT artificialH CH2CH2CH3 CH2CH2CH3N,N-dipropyltryptamine61-52-9
Propylisopropyltryptamine.svg PiPT artificialHCH2CH2CH3CH(CH3)2N-Propyl-N-isopropyltryptamine1354632-00-0
DiPT.svg DiPT artificialH CH(CH3)2 CH(CH3)2N,N-diisopropyltryptamine14780-24-6
EBT structure.png EBTartificialHCH2CH3(CH2)3CH3N-ethyl-N-butyltryptamine
PBT structure.png PBTartificialHCH2CH2CH3(CH2)3CH3N-propyl-N-butyltryptamine
IPsBT structure.png iPsBTartificialHCH(CH3)2CH(CH3)CH2CH3N-isopropyl-N-sec-butyltryptamine
Dibutyltryptamine.svg DBT artificialH(CH2)3CH3(CH2)3CH3N,N-dibutyltryptamine15741-77-2
DIBT structure.png DIBTartificialHCH2CH(CH3)2CH2CH(CH3)2N,N-diisobutyltryptamine63938-64-7
DSBT structure.png DSBTartificialHCH(CH3)CH2CH3CH(CH3)CH2CH3N,N-disecbutyltryptamine
Methylallyltryptamine.svg MALT artificialHCH3H2C=CH-CH2N-methyl-N-allyltryptamine1366416-29-6
DALT-structure.png DALT artificialH H2C=CH-CH2 H2C=CH-CH2N,N-diallyltryptamine60676-77-9
ALiPT structure.png ALiPTartificialHH2C=CH-CH2CH(CH3)2N-allyl-N-isopropyltryptamine
2-Me-DMT.svg 2-Methyl-DMT artificial2-CH3CH3CH3(2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine1080-95-1
2-methyl-diethyltryptamine.png 2-Me-DET artificial2-CH3CH2CH3CH2CH3N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine26628-88-6
4-Amino-DMT structure.png 4-Amino-DMT [5] artificial4-NH2CH3CH34-amino-N,N-dimethyltryptamine60331-61-5
4-Me-DMT structure.png 4-Methyl-DMTartificial4-CH3CH3CH34,N,N-trimethyltryptamine28289-23-8
4-MeO-DMT.png 4-MeO-DMT artificial4-OCH3CH3CH34-methoxy-N,N-dimethyltryptamine3965-97-7
4-MeO-MiPT.png 4-MeO-MiPT artificial4-OCH3CH3CH(CH3)24-methoxy-N-methyl-N-isopropyltryptamine96096-53-6
4-MeO-DiPT structure.png 4-MeO-DiPTartificial4-OCH3CH(CH3)2CH(CH3)24-methoxy-N,N-diisopropyltryptamine
O-Acetylpsilocin chemical structure.png 4-AcO-DMT artificial4-OCOCH3CH3CH34-acetoxy-N,N-dimethyltryptamine92292-84-7
4-PrO-DMT.svg 4-PrO-DMT artificial4-OCOCH2CH3CH3CH34-propionyloxy-N,N-dimethyltryptamine1373882-11-1
4-HO-MET.svg 4-HO-MET artificial4-OHCH3CH2CH34-hydroxy-N-methyl-N-ethyltryptamine77872-41-4
4-Acetoxy-N-methyl-N-ethyltryptamine.svg 4-Acetoxy-MET artificial4-OCOCH3CH3CH2CH34-acetoxy-N-methyl-N-ethyltryptamine1445751-40-5
4-PO-MET structure.png 4-PO-METartificial4-OPO3H2CH3CH2CH34-phosphoryloxy-N-methyl-N-ethyltryptamine
4-HO-DET.svg 4-HO-DET artificial4-OHCH2CH3CH2CH34-hydroxy-N,N-diethyltryptamine22204-89-3
4-Acetoxy-DET.png 4-Acetoxy-DET artificial4-OCOCH3CH2CH3CH2CH34-acetoxy-N,N-diethyltryptamine1135424-15-5
Ethocybin.png 4-PO-DET artificial4-OPO3H2CH2CH3CH2CH34-phosphoryloxy-N,N-diethyltryptamine60480-02-6
4-Hydroxy-N-ethyl-N-propyltryptamine.svg 4-HO-EPT artificial4-OHCH2CH3CH2CH2CH34-hydroxy-N-ethyl-N-propyltryptamine2595431-59-5
4-PO-EPT structure.png 4-PO-EPTartificial4-OPO3H2CH2CH3CH2CH2CH34-phosphoryloxy-N-ethyl-N-propyltryptamine
4-AcO-EiPT Structure.svg 4-AcO-EiPTartificial4-OCOCH3CH2CH3CH(CH3)24-acetoxy-N-ethyl-N-isopropyltryptamine
4-HO-MPT.svg 4-HO-MPT artificial4-OHCH3CH2CH2CH34-hydroxy-N-methyl-N-propyltryptamine763035-03-6
4-HO-MiPT.svg 4-HO-MiPT artificial4-OHCH(CH3)2CH34-hydroxy-N-isopropyl-N-methyltryptamine77872-43-6
4-Acetoxy-MiPT.svg 4-Acetoxy-MiPT artificial4-OCOCH3CH3CH(CH3)24-acetoxy-N-methyl-N-isopropyltryptamine1024612-25-6
4-HO-MALT structure.png 4-HO-MALT [6] artificial4-OHCH3H2C=CH-CH24-hydroxy-N-Methyl-N-allyltryptamine
4-AcO-MALT structure.png 4-AcO-MALT [7] artificial4-OCOCH3CH3H2C=CH-CH24-acetoxy-N-Methyl-N-allyltryptamine
4-HO-NALT structure.png 4-HO-NALT [8] artificial4-OHHH2C=CH-CH24-hydroxy-N-allyltryptamine
4-HO-MSBT structure.png 4-HO-MSBTartificial4-OHCH(CH3)CH2CH3CH34-hydroxy-N-sec-butyl-N-methyltryptamine
4-HO-EiBT structure.png 4-HO-EiBT artificial [9] 4-OHCH2CH(CH3)2CH2CH34-hydroxy-N-iso-butyl-N-ethyltryptamine
4-HO-McPT.svg 4-HO-McPT artificial4-OHC3H5CH34-hydroxy-N-cyclopropyl-N-methyltryptamine2883663-05-4
4-HO-McPeT.svg 4-HO-McPeT artificial4-OHC5H9CH34-hydroxy-N-cyclopentyl-N-methyltryptamine77872-48-1
4-OH-McPMT structure.png 4-HO-McPMT [10] artificial4-OHCH2C3H5CH34-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
4-HO-DPT.svg 4-HO-DPT artificial4-OHCH2CH2CH3CH2CH2CH34-hydroxy-N,N-dipropyltryptamine63065-88-3
4-AcO-DPT Structure.svg 4-AcO-DPT artificial4-OCOCH3CH2CH2CH3CH2CH2CH34-acetoxy-N,N-dipropyltryptamine1445751-75-6
4-HO-PiPT structure.png 4-HO-PiPT artificial4-OHCH2CH2CH3CH(CH3)24-hydroxy-N-propyl-N-isopropyltryptamine
4-AcO-PiPT structure.png 4-AcO-PiPTartificial4-OCOCH3CH2CH2CH3CH(CH3)24-acetoxy-N-propyl-N-isopropyltryptamine
4-HO-DIPT.SVG 4-HO-DIPT artificial4-OHCH(CH3)2CH(CH3)24-hydroxy-N,N-diisopropyltryptamine132328-45-1
4-AcO-DiPT.svg 4-Acetoxy-DiPT artificial4-OCOCH3CH(CH3)2CH(CH3)24-acetoxy-N,N-diisopropyltryptamine936015-60-0
4-PrO-DiPT structure.png 4-PrO-DiPTartificial4-OCOCH2CH3CH(CH3)2CH(CH3)24-propionyloxy-N,N-diisopropyltryptamine1373882-13-3
FT-104 structure.png FT-104 artificial4-OCO(CH2)3COOHCH(CH3)2CH(CH3)24-glutaryloxy-N,N-diisopropyltryptamine
4-PO-DiPT structure.png 4-PO-DiPTartificial4-OPO3H2CH(CH3)2CH(CH3)24-phosphoryloxy-N,N-diisopropyltryptamine1373882-09-7
4-HO-DALT structure.png 4-HO-DALTartificial4-OHH2C=CH-CH2H2C=CH-CH24-hydroxy-N,N-diallyltryptamine
4-AcO-DALT.svg 4-AcO-DALT artificial4-OCOCH3H2C=CH-CH2H2C=CH-CH24-acetoxy-N,N-diallyltryptamine1445751-71-2
4-HO-DBT.svg 4-HO-DBT artificial4-OH(CH2)3CH3(CH2)3CH34-hydroxy-N,N-dibutyltryptamine63065-89-4
4-HO-DIBT structure.png 4-HO-DIBTartificial4-OHCH2CH(CH3)2CH2CH(CH3)24-hydroxy-N,N-diisobutyltryptamine
4-HO-DSBT.svg 4-HO-DSBT artificial4-OHCH(CH3)CH2CH3CH(CH3)CH2CH34-hydroxy-N,N-disecbutyltryptamine127507-01-1
5-MeO-MET.svg 5-MeO-MET artificial5-OCH3CH2CH3CH35-methoxy-N-Methyl-N-ethyltryptamine16977-53-0
5-MeO-DET.svg 5-MeO-DET artificial5-OCH3CH2CH3CH2CH35-methoxy-N,N-diethyltryptamine2454-70-8
5-MeO-MPT structure.png 5-MeO-MPTartificial5-OCH3CH3CH2CH2CH35-methoxy-N-methyl-N-propyltryptamine
5-MeO-EPT.svg 5-MeO-EPT artificial5-OCH3CH2CH3CH2CH2CH35-methoxy-N-ethyl-N-propyltryptamine850032-67-6
5-MeO-DPT.svg 5-MeO-DPT artificial5-OCH3CH2CH2CH3CH2CH2CH35-methoxy-N,N-dipropyltryptamine69496-75-9
5-MeO-MALT.png 5-MeO-MALT artificial5-OCH3 H2C=CH-CH2 CH35-methoxy-N-Methyl-N-allyltryptamine1373918-64-9
5-MeO-DALT.svg 5-MeO-DALT artificial5-OCH3 H2C=CH-CH2 H2C=CH-CH25-methoxy-N,N-diallyltryptamine928822-98-4
5-MeO-ALiPT structure.png 5-MeO-ALiPTartificial5-OCH3H2C=CH-CH2CH2CH(CH3)25-methoxy-N-allyl-N-isopropyltryptamine
5-MeO-MiPT.svg 5-MeO-MiPT artificial5-OCH3CH3CH(CH3)25-methoxy-N,N-methylisopropyltryptamine96096-55-8
5,6-MeO-MiPT.svg 5,6-MeO-MiPT artificial5-OCH3, 6-OCH3CH3CH(CH3)25,6-dimethoxy-N,N-methylisopropyltryptamine
5-MeO-McPT structure.png 5-MeO-McPTartificial5-OCH3CH3C3H55-methoxy-N-methyl-N-cyclopropyltryptamine
5-MeO-McBT structure.png 5-MeO-McBTartificial5-OCH3CH3C4H75-methoxy-N-methyl-N-cyclobutyltryptamine
5-MeO-EiPT structure.png 5-MeO-EiPT artificial5-OCH3CH2CH3CH(CH3)25-methoxy-N-ethyl-N-isopropyltryptamine850032-66-5
5-MeO-PiPT structure.png 5-MeO-PiPT artificial5-OCH3CH2CH2CH3CH(CH3)25-methoxy-N-propyl-N-isopropyltryptamine
5-MeO-DiPT.svg 5-MeO-DIPT artificial5-OCH3CH(CH3)2CH(CH3)25-methoxy-N,N-diisopropyltryptamine4021-34-5
5-MeO-DBT.svg 5-MeO-DBT artificial5-OCH3(CH2)3CH3(CH2)3CH35-methoxy-N,N-dibutyltryptamine73785-42-9
5-MeO-DsBT structure.png 5-MeO-DSBT artificial5-OCH3CH(CH3)CH2CH3CH(CH3)CH2CH35-methoxy-N,N-di-sec-butyltryptamine
5-MeS-DMT.svg 5-MeS-DMT artificial5-SCH3CH3CH35-methylthio-N,N-dimethyltryptamine5102-11-4
5-AcO-DMT.svg 5-AcO-DMT artificial5-OCOCH3CH3CH35-acetoxy-N,N-dimethyltryptamine16977-50-7
5-AcO-MET structure.png 5-AcO-MET [11] artificial5-OCOCH3CH3CH2CH35-acetoxy-N-methyl-N-ethyltryptamine
5-AcO-DET structure.png 5-AcO-DETartificial5-OCOCH3CH2CH3CH2CH35-acetoxy-N,N-diethyltryptamine
5-AcO-EPT structure.png 5-AcO-EPT [12] artificial5-OCOCH3CH2CH3CH2CH2CH35-acetoxy-N-ethyl-N-propyltryptamine
5-AcO-DPT structure.png 5-AcO-DPTartificial5-OCOCH3CH2CH2CH3CH2CH2CH35-acetoxy-N,N-dipropyltryptamine
5-AcO-MiPT structure.png 5-AcO-MiPTartificial5-OCOCH3CH3CH(CH3)25-acetoxy-N-methyl-N-isopropyltryptamine
5-AcO-DiPT structure.png 5-AcO-DiPTartificial5-OCOCH3CH(CH3)2CH(CH3)25-acetoxy-N,N-diisopropyltryptamine
5-EtO-DMT Structure.svg 5-Ethoxy-DMT artificial5-OCH2CH3CH3CH35-ethoxy-N,N-dimethyltryptamine855245-09-9
5-EtO-MET structure.png 5-Ethoxy-METartificial5-OCH2CH3CH3CH2CH35-ethoxy-N-methyl-N-ethyltryptamine
5-EtO-DET structure.png 5-Ethoxy-DETartificial5-OCH2CH3CH2CH3CH2CH35-ethoxy-N,N-diethyltryptamine
5-EtO-MPT structure.png 5-Ethoxy-MPTartificial5-OCH2CH3CH3CH2CH2CH35-ethoxy-N-methyl-N-propyltryptamine
5-EtO-EPT structure.png 5-Ethoxy-EPTartificial5-OCH2CH3CH2CH3CH2CH2CH35-ethoxy-N-ethyl-N-propyltryptamine
5-EtO-DPT structure.png 5-Ethoxy-DPTartificial5-OCH2CH3CH2CH2CH3CH2CH35-ethoxy-N,N-dipropyltryptamine
5-EtO-MiPT structure.png 5-Ethoxy-MiPTartificial5-OCH2CH3CH3CH(CH3)25-ethoxy-N-methyl-N-isopropyltryptamine
5-EtO-EiPT structure.png 5-Ethoxy-EiPTartificial5-OCH2CH3CH2CH3CH(CH3)25-ethoxy-N-ethyl-N-isopropyltryptamine
5-EtO-DiPT structure.png 5-Ethoxy-DiPTartificial5-OCH2CH3CH(CH3)2CH(CH3)25-ethoxy-N,N-diisopropyltryptamine
5-EtO-DALT structure.png 5-Ethoxy-DALTartificial5-OCH2CH3H2C=CH-CH2H2C=CH-CH25-ethoxy-N,N-diallyltryptamine
5-BnO-DMT structure.png 5-BnO-DMTartificial5-OCH2C6H5CH3CH35-benzyloxy-N,N-dimethyltryptamine101832-88-6
5-OH-DET structure.png 5-HO-DETartificial5-OHCH2CH3CH2CH35-hydroxy-N,N-diethyltryptamine14009-42-8
5-OH-DPT structure.png 5-HO-DPTartificial5-OHCH2CH2CH3CH2CH2CH35-hydroxy-N,N-dipropyltryptamine36288-75-2
5-OH-MiPT structure.png 5-HO-MiPTartificial5-OHCH3CH(CH3)25-hydroxy-N-methyl-N-isopropyltryptamine
5-HO-DiPT.svg 5-HO-DiPT artificial5-OHCH(CH3)2CH(CH3)25-hydroxy-N,N-diisopropyltryptamine36288-76-3
5,N,N-TMT.svg 5-Methyl-DMT (5,N,N-TMT)artificial5-CH3CH3CH35,N,N-trimethyltryptamine22120-39-4
5-Ethyl-DMT.svg 5-Ethyl-DMT artificial5-CH2CH3CH3CH35-ethyl-N,N-dimethyltryptamine171783-25-8
5-iPr-DMT structure.png 5-Isopropyl-DMTartificial5-CH(CH3)2CH3CH35-isopropyl-N,N-dimethyltryptamine156281-04-8
5-tBu-DMT structure.png 5-(t-Butyl)-DMT [13] artificial5-C(CH3)3CH3CH35-(tert-butyl)-N,N-dimethyltryptamine
5-Fluoro-DMT structure.png 5-Fluoro-DMT artificial5-FCH3CH35-fluoro-N,N-dimethyltryptamine22120-36-1
5-F-MET.svg 5-Fluoro-MET artificial5-FCH3CH2CH35-fluoro-N-methyl-N-ethyltryptamine
5-Fluoro-DET.svg 5-Fluoro-DET artificial5-FCH2CH3CH2CH35-fluoro-N,N-diethyltryptamine
5-Fluoro-EPT.svg 5-Fluoro-EPT artificial5-FCH2CH3CH2CH2CH35-fluoro-N-ethyl-N-propyltryptamine
5-F-DPT structure.png 5-Fluoro-DPT artificial5-FCH2CH2CH3CH2CH2CH35-fluoro-N,N-dipropyltryptamine
5F-PiPT structure.png 5-Fluoro-PiPT artificial5-FCH2CH2CH3CH(CH3)25-fluoro-N-propyl-N-isopropyltryptamine
5F-PcBT structure.png 5-Fluoro-PcBT artificial5-FCH2CH2CH3CH(CH2)35-fluoro-N-propyl-N-cyclobutyltryptamine
5F-iPcBT structure.png 5-Fluoro-iPcBT artificial5-FCH(CH3)2CH(CH2)35-fluoro-N-isopropyl-N-cyclobutyltryptamine
5-F-DiPT structure.png 5-Fluoro-DiPT artificial5-FCH(CH3)2CH(CH3)25-fluoro-N,N-diisoproptryptamine
5F-sBALT structure.png 5-Fluoro-sBALT artificial5-FCH(CH3)CH2CH3CH2CH=CH25-fluoro-N-sec-butyl-N-allyltryptamine
5F-M1MALT structure.png 5-Fluoro-M1MALTartificial5-FCH3CH(CH3)CH=CH25-fluoro-N-methyl-N-(1-methylallyl)tryptamine
5-Chloro-DMT.svg 5-Chloro-DMT artificial5-ClCH3CH35-chloro-N,N-dimethyltryptamine22120-32-7
5-I-DMT structure.png 5-Iodo-DMT artificial5-ICH3CH35-iodo-N,N-dimethyltryptamine22120-38-3
5-TFM-DMT structure.png 5-TFM-DMT artificial5-CF3CH3CH35-(trifluoromethyl)-N,N-dimethyltryptamine2418713-32-1
5-TFMO-DMT structure.png 5-TFMO-DMT [14] artificial5-OCF3CH3CH35-(trifluoromethoxy)-N,N-dimethyltryptamine
5-NO2-DMT structure.png 5-Nitro-DMT [15] artificial5-NO2CH3CH35-nitro-N,N-dimethyltryptamine69937-13-9
5-CN-DMT structure.png 5-CN-DMT artificial5-C≡NCH3CH35-cyano-N,N-dimethyltryptamine17380-42-6
5-CN-DPT structure.png 5-CN-DPT artificial5-C≡NCH2CH2CH3CH2CH2CH35-cyano-N,N-dipropyltryptamine74885-19-1
Almotriptan skeletal.svg Almotriptan artificial5-(CH2SO2N(CH2)4)CH3CH3N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine154323-57-6
Rizatriptan Structural Formula V.1.svg Rizatriptan artificial5-(CH2(N3(CH)2))CH3CH3N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine145202-66-0
Sumatriptan.svg Sumatriptan artificial5-(CH2SO2NHCH3)CH3CH31-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide103628-46-2
Zolmitriptan Structure V.1.svg Zolmitriptan artificial5-(CHNHC=OOCH2)CH3CH35-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine139264-17-8
6-Fluoro-DMT skeletal.svg 6-Fluoro-DMT artificial6-FCH3CH36-fluoro-N,N-dimethyltryptamine1511-31-5
6-Fluoro-DET.svg 6-Fluoro-DET [16] artificial6-FCH2CH3CH2CH36-fluoro-N,N-diethyltryptamine2836-69-3
6-Cl-DMT structure.png 6-Chloro-DMTartificial6-ClCH3CH36-chloro-N,N-dimethyltryptamine25390-72-1
6-Me-DMT structure.png 6-Methyl-DMTartificial6-CH3CH3CH36,N,N-trimethyltryptamine
6-OH-DMT structure.png 6-Hydroxy-DMTartificial6-OHCH3CH36-hydroxy-N,N-dimethyltryptamine1476-33-1
6-OH-DET structure.png 6-Hydroxy-DETartificial6-OHCH3CH36-hydroxy-N,N-diethyltryptamine1476-59-1
6-MeO-DMT structure.png 6-Methoxy-DMTartificial6-OCH3CH3CH36-methoxy-N,N-dimethyltryptamine2426-88-2
7-TMT structure.png 7-Methyl-DMT artificial7-CH3CH3CH37,N,N-trimethyltryptamine65882-39-5
7-Et-DMT structure.png 7-Ethyl-DMTartificial7-CH2CH3CH3CH37-ethyl-N,N-dimethyltryptamine
7-Cl-DMT structure.png 7-Chloro-DMTartificial7-ClCH3CH37-chloro-N,N-dimethyltryptamine
7-Br-DMT structure.png 7-Bromo-DMT [17] artificial7-BrCH3CH37-bromo-N,N-dimethyltryptamine74798-68-8
7-MeO-DMT structure.png 7-Methoxy-DMTartificial7-OCH3CH3CH37-methoxy-N,N-dimethyltryptamine
7-MeO-MiPT structure.png 7-Methoxy-MiPTartificial7-OCH3CH3CH(CH3)27-methoxy-N-methyl-N-isopropyltryptamine
1-Methylpsilocin.svg 1-Methylpsilocin artificial1-CH3, 4-OHCH3CH31-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole1465-16-3
1-Me-5-MeO-DiPT.svg 1-Methyl-5-MeO-DiPTartificial1-CH3, 5-OCH3CH(CH3)2CH(CH3)21-methyl-5-methoxy-N,N-diisopropyltryptamine1373882-10-0
NB-5-MeO-MiPT structure.png NB-5-MeO-MiPTartificial1-OCOC(CH3)3, 5-OCH3CH3CH(CH3)21-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
NB-5-MeO-DALT structure.png NB-5-MeO-DALTartificial1-OCOC(CH3)3, 5-OCH3H2C=CH-CH2H2C=CH-CH21-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine
6-Fluoropsilocin structure.png 6-Fluoropsilocinartificial4-OH,6-FCH3CH34-hydroxy-6-fluoro-N,N-dimethyltryptamine312314-12-8
6F-5-MeO-DMT structure.png 6-Fluoro-5-MeO-DMTartificial5-OCH3,6-FCH3CH35-methoxy-6-fluoro-N,N-dimethyltryptamine
56DF-EPT structure.png 5,6-Difluoro-EPTartificial5-F, 6-FCH2CH3CH2CH2CH35,6-difluoro-N-ethyl-N-propyltryptamine
5-MeO-2,N,N-TMT.svg 5-MeO-2-TMT artificial2-CH3, 5-OCH3CH3CH32-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine67292-68-6
5-MeO-7-TMT.png 5-Methoxy-7,N,N-trimethyltryptamine artificial5-OCH3, 7-CH3CH3CH35-Methoxy-7,N,N-trimethyltryptamine61018-77-7
5-MeO-4NN-TMT structure.png 5-Methoxy-4,N,N-trimethyltryptamineartificial4-CH3, 5-OCH3CH3CH35-Methoxy-4,N,N-trimethyltryptamine
4-HO-5-MeO-DMT.svg 4-HO-5-MeO-DMT artificial4-OH, 5-OCH3CH3CH34-Hydroxy-5-methoxy-N,N-dimethyltryptamine2433-31-0
4-Fluoro-5-methoxy-N,N-dimethyltryptamine.svg 4-F-5-MeO-DMT artificial4-F, 5-OCH3CH3CH34-Fluoro-5-Methoxy-N,N-dimethyltryptamine312314-18-4
7F-5-MeO-MET structure.png 5-methoxy-7-fluoro-MET artificial5-OCH3, 7-FCH3CH2CH35-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
EMDT structure.svg EMDT artificial2-CH2CH3, 5-OCH3CH3CH32-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine263744-72-5
ST-1936 structure.svg ST-1936 artificial2-CH3, 5-ClCH3CH32-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine1210-81-7
O-4310 structure.svg O-4310 artificial1-CH(CH3)2, 4-OH, 6-FCH3CH33-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol885671-63-6
CP-132,484 Structure.svg CP-132,484 artificial1-methyl-4,5-(OCH2CH2CH2)HH1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole143508-76-3
4,5-DHP-DMT.svg 4,5-DHP-DMT artificial4,5-(OCH2CH2CH2)CH3CH31-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole135360-97-3
4,5-DHF-DMT structure.png 4,5-DHF-DMT (P-3)artificial [18] 4,5-(CH2CH2O)CH3CH32-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
4,5-Methylbenzodioxole-DMT structure.png 4,5-Methylbenzodioxole-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-DMT.svg 4,5-MDO-DMT artificial4,5-(OCH2O)CH3CH32-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine81249-30-1
4,5-MDO-DiPT.svg 4,5-MDO-DiPT artificial4,5-(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 structure.png 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-DMT.svg 5,6-MDO-DMT artificial5,6-(OCH2O)CH3CH32-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine
5,6-MDO-MiPT.svg 5,6-MDO-MiPT artificial5,6-(OCH2O)CH3CH(CH3)2N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine
5,6-MDO-DiPT.svg 5,6-MDO-DiPT artificial5,6-(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
Chemical StructureShort NameOriginRing SubstitutionRN1RN2Full NameCAS Number

List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen. [19] [20] [21] 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. [21] This is analogous to α-methylation of phenethylamine into amphetamine. [21]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors, [22] [23] [24] [25] and produce psychostimulant, entactogen, and/or psychedelic effects. [19] [20] [21] 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. [20] [21] 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. [26]

StructureCommon nameChemical nameCAS number
L-Tryptophan - L-Tryptophan.svg Tryptophan (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid73-22-3
5-Hydroxy-L-Tryptophan (5-HTP).svg 5-Hydroxytryptophan 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid4350-09-8
AMT.svg αMT 1-(1H-Indol-3-yl)propan-2-amine299-26-3
4-HO-aMT Structure.svg 4-HO-αMT 3-(2-aminopropyl)-1H-indol-4-ol15066-09-8
4-Methyl-AMT.png 4-Methyl-αMT 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine3569-29-7
5-fluoro-alpha-methyltryptamine.svg 5-Fluoro-αMT 1-(5-fluoro-1H-indol-3-yl)propan-2-amine712-08-3
5-Chloro-3-(2-aminopropyl)indole.svg 5-Chloro-αMT 1-(5-Chloro-1H-indol-3-yl)propan-2-amine712-07-2
5-HO-AMT structure.png 5-HO-αMT (αMS/α-methyl-5-HT)3-(2-aminopropyl)-1H-indol-5-ol304-52-9
5-MeO-AMT.svg 5-MeO-αMT 1-(5-methoxy-1H-indol-3-yl)propan-2-amine1137-04-8
5EtO-AMT structure.png 5-Ethoxy-αMT 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine101832-83-1
5-iPrO-AMT structure.png 5-Isopropoxy-αMT1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine
BW-723C86 structure.png BW-723C86 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine160521-72-2
6-fluoro-AMT structure.png 6-Fluoro-αMT 1-(6-fluoro-1H-indol-3-yl)propan-2-amine712-11-8
7-Cl-AMT structure.png 7-Chloro-AMT 1-(7-chloro-1H-indol-3-yl)propan-2-amine711-99-9
AL-37350A structure.png AL-37350A (4,5-dihydropyrano-αMT)(S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole362603-40-5
BIAP structure.png Compound 5 [27] 1-(3H-benzo[e]indol-1-yl)propan-2-amine
AET.svg αET 1-(1H-indol-3-yl)butan-2-amine2235-90-7
4-Methyl-AET.png 4-Methyl-αET 1-(4-Methyl-1H-indol-3-yl)butan-2-amine28289-30-7
4HO-AET structure.png 4-HO-αET1-(4-hydroxy-1H-indol-3-yl)butan-2-amine28289-28-3
5F-AET structure.png 5-Fluoro-αET 1-(5-fluoro-1H-indol-3-yl)butan-2-amine1380137-98-3
5Me-AET structure.png 5-Methyl-αET 1-(5-methyl-1H-indol-3-yl)butan-2-amine1380148-21-9
5-MeO-AET.svg 5-MeO-αET 1-(5-methoxy-1H-indol-3-yl)butan-2-amine4765-10-0
7-Methyl-AET.png 7-Methyl-αET 1-(7-methyl-1H-indol-3-yl)butan-2-amine13712-80-6
A,N,O-TMS.png 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.svg Indolylpropylaminopentane (α,N-DPT)1-(1H-indol-3-yl)-N-propylpentan-2-amine
A,N,N-TMT.png N,N-Dimethyl-αMT (α,N,N-TMT)(2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine4761-32-4
5MeO-TMT structure.png 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
AMDIPT structure.png αMDiPT(2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
MPMI structure.png MPMI [28] 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143321-54-4
4-HO-N-Me-TMT.png Lucigenol (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole250672-65-2
5-MeO-N-Me-TMT.svg 5-MeO-MPMI 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole143321-57-7
R5F-MPMI structure.png 5F-MPMI [29] (R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole
5Br-MPMI structure.png 5-Br-MPMI5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143322-57-0
Eletriptan skeletal.svg Eletriptan 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole143322-58-1
Z5247692566 structure.png Z5247692566 [4] [30] 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine
BK-NM-AMT (α,N-dimethyl-β-ketotryptamine) [31] [32] [33] 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5F-NM-AMT structure.png BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine) [34] [35] [36] [33] 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine) [36] [37] [38] 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Br-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine) [36] [39] [40] 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one

A number of related compounds are known, with a similar structure but having the indole core flipped and/or replaced with related cores such as indoline, indazole, benzothiophene, or benzofuran. These similarly 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.

StructureCommon nameChemical nameCAS number
Dimemebfe.png Dimemebfe 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine140853-58-3
5-MeO-DiBF.svg 5-MeO-DiBF N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
3APB structure.png 3-APB3-(2-aminopropyl)benzofuran105909-13-5
Mebfap structure.png Mebfap3-(2-aminopropyl)-5-methoxybenzofuran140853-59-4
Ro60-0175 structure.png Ro60-0175 (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine169675-09-6
AAZ-A-154 structure.png AAZ-A-154 (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine
Example16 structure.png Example 16 [41] [42] 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
US7012090-1 structure.png Example 1 [43] 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine
VER-3323 structure.png VER-3323 (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine259857-99-3
AL-34662 structure.png AL-34662 1-((S)-2-Aminopropyl)-1H-indazol-6-ol210580-75-9
O-methyl-AL34662 structure.png O-methyl-AL-346621-((S)-6-methoxy-2-aminopropyl)-1H-indazole210580-60-2
7-methyl-AL34662 structure.png 7-methyl-AL-346621-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol874668-67-4
7-chloro-AL34662 structure.png 7-chloro-AL-346621-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol874881-86-4
AL-38022A structure.png AL-38022A (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine478132-11-5
US6881749-9 structure.png Example 9 [44] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine478132-12-6
US7425572-3 structure.png Example 3 [45] (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine890087-75-9
US7268131-1 structure.png Example 1 [46] (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine1373917-69-1
YM-348 structure.png YM-348 (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine372163-84-3
2-desethyl-YM348 structure.png 2-desethyl-YM-348 [47] (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine748116-94-1
I-32 structure.png I-32 [48] 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
2-Azapsilocin structure.png 2-Azapsilocin (Psilocin indazole analogue, P-6) [49] 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol
4-Aza-5-MeO-DPT structure.png 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 structure.png 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 structure.png 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
VU6067416.png VU6067416 [50] 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole
R69 structure.png (R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine
SN22 structure.png SN-22 3-(1-methylpiperidin-4-yl)-1H-indole17403-07-5

Tryptamine-based therapeutics

DrugMechanismTreatmentEffectStructure
Sumatriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Sumatriptan Sumatriptan.svg
Sumatriptan
Rizatriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Rizatriptan Rizatriptan.png
Rizatriptan
Zolmitriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Zolmitriptan Zolmitriptan.svg
Zolmitriptan
Almotriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Almotriptan Almotriptan skeletal.svg
Almotriptan
Eletriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Eletriptan Eletriptan skeletal.svg
Eletriptan
Frovatriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Frovatriptan Frovatriptan 2.png
Frovatriptan
Naratriptan [51] 5-HT1B and 5-HT1D agonistMigraine Headaches Vasoconstriction of brain blood vessels
Naratriptan Naratriptan.svg
Naratriptan

Further reading

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α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine family. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

<span class="mw-page-title-main">Tryptamine</span> Metabolite of the amino acid tryptophan

Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon. The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.

α-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">Benzofuranylpropylaminopentane</span> Chemical compound

(–)-Benzofuranylpropylaminopentane is an experimental drug related to selegiline which acts as a monoaminergic activity enhancer (MAE). It is orally active in animals.

<span class="mw-page-title-main">Phenylpropylaminopentane</span> Stimulant drug of the substituted phenethylamine class

1-Phenyl-2-propylaminopentane is an experimental drug related to selegiline which acts as a catecholaminergic activity enhancer (CAE).

<span class="mw-page-title-main">AL-34662</span> Chemical compound

AL-34662 is an indazole derivative drug that is being developed for the treatment of glaucoma. It acts as a selective serotonin 5-HT2A receptor agonist, the same target as that of psychedelic drugs like psilocin, but unlike these drugs, AL-34662 was designed specifically as a peripherally selective drug, which does not cross the blood–brain barrier. This means that AL-34662 can exploit a useful side effect of the hallucinogenic 5-HT2A receptor agonists, namely reduction in intra-ocular pressure and hence relief from the symptoms of glaucoma, but without causing the psychedelic effects that make centrally active serotonin 5-HT2A receptor agonists unsuitable for clinical use. In animal studies, AL-34662 has been shown to be potent and effective in the treatment of symptoms of glaucoma, with minimal side effects.

α-Methylserotonin Chemical compound

α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.

<span class="mw-page-title-main">AM-694</span> Chemical compound

AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a designer drug that acts as a potent and selective agonist for the cannabinoid receptor CB1. It is used in scientific research for mapping the distribution of CB1 receptors.

A serotonin–dopamine releasing agent (SDRA) is a type of drug which induces the release of serotonin and dopamine in the body and/or brain.

DO<i>x</i> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, or simply cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

<span class="mw-page-title-main">A-834,735</span> Chemical compound

A-834,735 is a drug developed by Abbott Laboratories that acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors, with a Ki of 12 nM at CB1 and 0.21 nM at CB2. Replacing the aromatic 3-benzoyl or 3-naphthoyl group found in most indole derived cannabinoids with the 3-tetramethylcyclopropylmethanone group of A-834,735 and related compounds imparts significant selectivity for CB2, with most compounds from this group found to be highly selective CB2 agonists with little affinity for CB1. However, low nanomolar CB1 binding affinity is retained with certain heterocyclic 1-position substituents such as (N-methylpiperidin-2-yl)methyl (cf. AM-1220, AM-1248), or the (tetrahydropyran-4-yl)methyl substituent of A-834,735, resulting in compounds that still show significant affinity and efficacy at both receptors despite being CB2 selective overall.

<span class="mw-page-title-main">CP-132,484</span> Chemical compound

CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A over 5-HT2C. This compound and several related analogues have been shown to have ocular hypotensive activity in animal models, suggesting they may be useful for the treatment of glaucoma.

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%. It is likely to act as a potent agonist of other serotonin receptors as well.

<span class="mw-page-title-main">7-Chloro-AMT</span> Chemical compound

7-Chloro-α-methyltryptamine (7-Cl-AMT) is a tryptamine derivative with stimulant effects, invented in the 1960s. It is a weak monoamine oxidase inhibitor but its pharmacology has not otherwise been studied by modern techniques, though several closely related compounds are known to act as serotonin–dopamine releasing agents and agonists of the 5-HT2A receptor.

<span class="mw-page-title-main">5-Chloro-DMT</span> Chemical compound

5-Chloro-N,N-dimethyltryptamine (5-chloro-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-fluoro-DMT. It acts as a serotonin receptor agonist and has primarily sedative effects in animal studies. It has been sold as a designer drug.

<span class="mw-page-title-main">Indolylpropylaminopentane</span> A synthetic monoaminergic activity enhancer drug

Indolylpropylaminopentane (IPAP), also known as α,N-dipropyltryptamine (α,N-DPT), is a monoaminergic activity enhancer (MAE) that is closely related to benzofuranylpropylaminopentane (BPAP) and phenylpropylaminopentane (PPAP). It is a tryptamine derivative and the corresponding analogue of PPAP and BPAP with an indole ring instead of a benzene ring or benzofuran ring, respectively. IPAP is also a positional isomer of N,N-dipropyltryptamine (N,N-DPT). MAEs are agents that enhance the action potential-mediated release of monoamine neurotransmitters.

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