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.

Substituted tryptamines, or serotonin 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
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

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 [31] [32] 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
US7012090-1 structure.png Example 1 [33] 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 [34] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine478132-12-6
US7425572-3 structure.png Example 3 [35] (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine890087-75-9
US7268131-1 structure.png Example 1 [36] (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 [37] (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine748116-94-1
I-32 structure.png I-32 [38] 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
2-Azapsilocin structure.png 2-Azapsilocin (Psilocin indazole analogue, P-6) [39] 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 [40] 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

Further reading

See also

Related Research Articles

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by chemists at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

α-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.

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

Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A serotonin receptors, psilocin’s psychedelic effects are directly correlated with the drug's occupancy at these receptor sites. The subjective mind-altering effects of psilocin are highly variable and are said to resemble those of LSD and DMT.

<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">(+)-CPCA</span> Stimulant drug

(+)-CPCA is a stimulant drug similar in structure to pethidine and to RTI-31, but nocaine lacks the two-carbon bridge of RTI-31's tropane skeleton. This compound was first developed as a substitute agent for cocaine.

<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 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 agonists, namely reduction in intra-ocular pressure and hence relief from the symptoms of glaucoma, but without causing the hallucinogenic effects that make centrally active 5-HT2A 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.

<span class="mw-page-title-main">AL-37350A</span> Chemical compound

AL-37350A (4,5-DHP-AMT) is a tricyclic tryptamine derivative which acts as a potent and selective agonist for the serotonin receptor 5-HT2A, with a Ki of 2.0 nM, and moderate selectivity over the related 5-HT2B and 5-HT2C receptors. It has been shown to have ocular hypotensive activity in animal models, suggesting it may be useful for the treatment of glaucoma.

5-Methoxy-7,<i>N</i>,<i>N</i>-trimethyltryptamine Chemical compound

5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), is a tryptamine derivative which acts as a partial agonist at the 5-HT2 serotonin receptors, with an EC50 of 63.9 nM and an efficacy of 66.2% at 5-HT2A (vs 5-HT), and weaker activity at 5-HT2B and 5-HT2C. In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite high 5-HT2 receptor binding affinity, suggesting these may be antagonists or weak partial agonists for the 5-HT2 receptors. The related compound 7-MeO-MiPT (cf. 5-MeO-MiPT) was also found to be inactive, suggesting that the 7-position has poor tolerance for bulky groups at this position, at least if agonist activity is desired.

<span class="mw-page-title-main">7,N,N-TMT</span> Chemical compound

7,N,N-trimethyltryptamine (7-methyl-DMT, 7-TMT), is a tryptamine derivative which acts as an agonist of 5-HT2 receptors. In animal tests, both 7-TMT and its 5-methoxy derivative 5-MeO-7-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT, but the larger 7-ethyl and 7-bromo derivatives of DMT did not produce psychedelic responses despite having higher 5-HT2 receptor affinity in vitro (cf. DOBU, DOAM). 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.

<span class="mw-page-title-main">7-Methyl-α-ethyltryptamine</span> Chemical compound

7-Methyl-α-ethyltryptamine (7-Me-αET) is a tryptamine derivative related to α-ethyltryptamine (αET). It was discovered by a team at Upjohn in the early 1960s. It has similar pharmacological effects to αET, but is both 3-4 times more potent as a serotonin releasing agent, and 10 times more potent as a monoamine oxidase inhibitor, making it potentially hazardous as this pharmacological profile is shared with drugs such as PMA and 4-MTA, which are known to be dangerous in humans when used at high doses.

<span class="mw-page-title-main">4,5-DHP-DMT</span> Chemical compound

1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT2A, with a Ki of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT2 affinity and efficacy than the related compound AL-37350A, but higher lipophilicity.

<span class="mw-page-title-main">MN-25</span> Chemical compound

MN-25 (UR-12) is a drug invented by Bristol-Myers Squibb, that acts as a reasonably selective agonist of peripheral cannabinoid receptors. It has moderate affinity for CB2 receptors with a Ki of 11 nM, but 22x lower affinity for the psychoactive CB1 receptors with a Ki of 245 nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a Ki of 8 nM at CB1 and 29 nM at CB2, which contrasts with the usual trend of 2-methyl derivatives having increased selectivity for CB2 (cf. JWH-018 vs JWH-007, JWH-081 vs JWH-098).

<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">Substituted phenylmorpholine</span> Class of chemical compounds

Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.

<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-Fluoro-AET</span> Chemical compound

5-Fluoro-α-ethyltryptamine (5-F-AET) is a tryptamine derivative which acts as a serotonin–dopamine releasing agent and agonist of the 5-HT2A receptor.

<span class="mw-page-title-main">5-Fluoro-DET</span> Chemical compound

5-Fluoro-DET is a tryptamine derivative related to drugs such as DET and 5-MeO-DET. It acts as an inhibitor of the enzyme myeloperoxidase, and is also thought to be an agonist at the 5-HT2A receptor.

<span class="mw-page-title-main">RS134-49</span> Chemical compound

RS134-49 is a tetrahydropyridine derivative related to psychedelic tryptamines which acts as a 5-HT2A receptor agonist, with a 5-HT2A Ki of 11.5nM and an EC50 of 22nM. It is a biased agonist selective for activation of the Gq coupled signalling pathway with weaker activation of the β-arrestin 2 coupled pathway, but shows a more balanced profile than related compounds such as (R)-69.

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