Substituted tryptamine explained

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.

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
Animals, plants, fungi H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine 61-54-1
Plants H H CH3 N-methyltryptamine 61-49-4
Plants 2-OH H CH3 2-hydroxy-N-methyltryptamine 106987-89-7
Plants 5-OCH3 H CH3 5-methoxy-N-methyltryptamine 2009-03-2
Animals, plants 5-OH H H 5-hydroxytryptamine 50-67-9
Nω-Methylserotonin (norbufotenin)Plants 5-OH H CH3 5-hydroxy-N-methyltryptamine 1134-01-6
Animals, plants, fungi 5-OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine 487-93-4
Amphibians 5-O− (CH3)3 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate 487-91-2
MelatoninAnimals, plants, microbes H 5-methoxy-N-acetyltryptamine 73-31-4
N-AcetylserotoninAnimals 5-OH H O=C-CH3 5-hydroxy-N-acetyltryptamine 1210-83-9
Animals 5-OCH3, 6-OH H O=C-CH3 N-[2-(6-Hydroxy-5-methoxy-1''H''-indol-3-yl)ethyl]acetamide 2208-41-5
Fungi H CH3 4-hydroxy-N-methyltryptamine 28363-70-4
Fungi CH3 CH3 4-hydroxy-N,N-dimethyltryptamine 520-53-6
Fungi 4-OPO3H2 H H 4-phosphoryloxy-tryptamine 21420-59-7
BaeocystinFungi 4-OPO3H2 H CH3 4-phosphoryloxy-N-methyl-tryptamine 21420-58-6
Fungi 4-OPO3H2 CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine 520-52-5
Fungi 4-OPO3H2 (CH3)3 [3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate 114264-95-8
Animals, plants H CH3 N,N-dimethyltryptamine 61-50-7
Plants 1-OCH3 CH3 CH3 1-methoxy-N,N-dimethyltryptamine 4335-93-7
5-MeO-DMTAnimals, plants 5-OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine 1019-45-0
5-Bromo-DMTMarine sponges, invertebrates 5-Br CH3 CH3 5-bromo-N,N-dimethyltryptamine 17274-65-6
Marine invertebrates 6-Br H H 6-bromotryptamine 96624-18-9
Marine invertebrates 5,6-Br H H 5,6-dibromotryptamine
Marine invertebrates 5,6-Br H CH3 5,6-dibromo-N-methyltryptamine
Marine sponges, invertebrates 5,6-Br CH3 CH3 5,6-dibromo-N,N-dimethyltryptamine 72853-80-6
DesformylflustrabromineMarine invertebrates 2-(α,α-dimethylallyl), 6-Br H CH3 2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine 474657-72-2
Marine invertebrates 2,4,6-Br, 1,7-OCH3 CH3 CH3 1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine 443356-86-3
Acetryptineartificial5-COCH3HH5-Acetyltryptamine3551-18-6
5-BTartificial5-OCH2C6H5HH5-Benzyloxytryptamine20776-45-8
5-CTartificial5-CONH2HH5-Carboxamidotryptamine74885-09-9
5-(Nonyloxy)tryptamineartificial5-O(CH2)8CH3 H H 5-nonyloxytryptamine 157798-12-4
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-amine
5-MeO-T-NBOMeartificial5-OCH3HCH2C6H4(o-OCH3)5-methoxy-N-(ortho-methoxybenzyl)tryptamine1335331-37-7
5-MT-NB3OMe [2] 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 [3] 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-tetrafluoropropoxy)benzyl)ethanamine467459-31-0
Z2876442907[4] artificial4-CH3HCH2(C3HNS)COOCH2CH3ethyl 2-(methyl)-1,3-thiazole-5-carboxylate
artificial H (CH2)4 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole 14008-96-9
artificial 4-OH (CH2)4 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol 63097-26-7
artificial 5-OCH3 (CH2)4 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole 3949-14-2
Indolylethylfentanyl artificial H (CH2)5-4-N(COCH2CH3)C6H5 N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide 58399-46-5
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
ALiPTartificialHH2C=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-Me-DETartificial2-CH3CH2CH3CH2CH3N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine26628-88-6
4-Amino-DMT [5] 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-HO-METartificial4-OHCH3CH2CH34-hydroxy-N-methyl-N-ethyltryptamine77872-41-4
4-Acetoxy-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-Acetoxy-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-Acetoxy-MiPTartificial4-OCOCH3CH3CH(CH3)24-acetoxy-N-methyl-N-isopropyltryptamine1024612-25-6
4-HO-MALT[6] artificial4-OHCH3H2C=CH-CH24-hydroxy-N-Methyl-N-allyltryptamine
4-AcO-MALT[7] artificial4-OCOCH3CH3H2C=CH-CH24-acetoxy-N-Methyl-N-allyltryptamine
4-HO-NALT[8] artificial4-OHHH2C=CH-CH24-hydroxy-N-allyltryptamine
4-HO-MSBTartificial4-OHCH(CH3)CH2CH3CH34-hydroxy-N-sec-butyl-N-methyltryptamine
4-HO-EiBTartificial[9] 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 [10] 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-Acetoxy-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
FT-104artificial4-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-diallyltryptamine
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
5-MeO-ALiPTartificial5-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-DMTartificial 5-SCH3 CH3 CH3 5-methylthio-N,N-dimethyltryptamine 5102-11-4
5-AcO-DMTartificial5-OCOCH3CH3CH35-acetoxy-N,N-dimethyltryptamine16977-50-7
5-AcO-MET [11] artificial5-OCOCH3CH3CH2CH35-acetoxy-N-methyl-N-ethyltryptamine
5-AcO-DETartificial5-OCOCH3CH2CH3CH2CH35-acetoxy-N,N-diethyltryptamine
5-AcO-EPT [12] 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
artificial5-OCH2CH3 CH3 CH3 5-ethoxy-N,N-dimethyltryptamine 855245-09-9
5-Ethoxy-MET artificial5-OCH2CH3 CH3 CH2CH3 5-ethoxy-N-methyl-N-ethyltryptamine
5-Ethoxy-DET artificial5-OCH2CH3 CH2CH3 CH2CH3 5-ethoxy-N,N-diethyltryptamine
5-Ethoxy-MPT artificial5-OCH2CH3 CH3 CH2CH2CH3 5-ethoxy-N-methyl-N-propyltryptamine
5-Ethoxy-EPT artificial5-OCH2CH3 CH2CH3 CH2CH2CH3 5-ethoxy-N-ethyl-N-propyltryptamine
5-Ethoxy-DPT artificial5-OCH2CH3 CH2CH2CH3 CH2CH3 5-ethoxy-N,N-dipropyltryptamine
5-Ethoxy-MiPT artificial5-OCH2CH3 CH3 CH(CH3)2 5-ethoxy-N-methyl-N-isopropyltryptamine
5-Ethoxy-EiPT artificial5-OCH2CH3 CH2CH3 CH(CH3)2 5-ethoxy-N-ethyl-N-isopropyltryptamine
5-Ethoxy-DiPT artificial5-OCH2CH3 CH(CH3)2 CH(CH3)2 5-ethoxy-N,N-diisopropyltryptamine
5-Ethoxy-DALT artificial5-OCH2CH3 H2C=CH-CH2 H2C=CH-CH2 5-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-CH3 CH3 CH3 5,N,N-trimethyltryptamine 22120-39-4
artificial5-CH2CH3 CH3 CH3 5-ethyl-N,N-dimethyltryptamine 171783-25-8
5-Isopropyl-DMT artificial5-CH(CH3)2 CH3 CH3 5-isopropyl-N,N-dimethyltryptamine 156281-04-8
5-(t-Butyl)-DMT [13] artificial5-C(CH3)3 CH3 CH3 5-(tert-butyl)-N,N-dimethyltryptamine
artificial5-F CH3 CH3 5-fluoro-N,N-dimethyltryptamine 22120-36-1
5-Fluoro-METartificial5-F CH3 CH2CH3 5-fluoro-N-methyl-N-ethyltryptamine
5-Fluoro-DETartificial5-F CH2CH3 CH2CH3 5-fluoro-N,N-diethyltryptamine
5-Fluoro-EPTartificial5-F CH2CH3 CH2CH2CH3 5-fluoro-N-ethyl-N-propyltryptamine
artificial5-F CH2CH2CH3 CH2CH2CH3 5-fluoro-N,N-dipropyltryptamine
artificial5-F CH2CH2CH3 CH(CH3)2 5-fluoro-N-propyl-N-isopropyltryptamine
artificial5-F CH2CH2CH3 CH(CH2)3 5-fluoro-N-propyl-N-cyclobutyltryptamine
artificial5-F CH(CH3)2 CH(CH2)3 5-fluoro-N-isopropyl-N-cyclobutyltryptamine
artificial5-F CH(CH3)2 CH(CH3)2 5-fluoro-N,N-diisoproptryptamine
artificial5-F CH(CH3)CH2CH3 CH2CH=CH2 5-fluoro-N-sec-butyl-N-allyltryptamine
5-Fluoro-M1MALTartificial5-F CH3 CH(CH3)CH=CH2 5-fluoro-N-methyl-N-(1-methylallyl)tryptamine
artificial5-Cl CH3 CH3 5-chloro-N,N-dimethyltryptamine 22120-32-7
artificial5-I CH3 CH3 5-iodo-N,N-dimethyltryptamine 22120-38-3
artificial5-CF3 CH3 CH3 5-(trifluoromethyl)-N,N-dimethyltryptamine 2418713-32-1
5-TFMO-DMT[14] artificial5-OCF3 CH3 CH3 5-(trifluoromethoxy)-N,N-dimethyltryptamine
5-Nitro-DMT[15] artificial5-NO2 CH3 CH3 5-nitro-N,N-dimethyltryptamine 69937-13-9
artificial5-C≡N CH3 CH3 5-cyano-N,N-dimethyltryptamine 17380-42-6
artificial5-C≡N CH2CH2CH3 CH2CH2CH3 5-cyano-N,N-dipropyltryptamine 74885-19-1
Almotriptanartificial5-(CH2SO2N(CH2)4)CH3CH3N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1''H''-indol-3-yl]-ethanamine154323-57-6
Rizatriptanartificial5-(CH2(N3(CH)2))CH3CH3N,N-dimethyl-2-[5-(1''H''-1,2,4-triazol-1-ylmethyl)-1''H''-indol-3-yl]ethanamine145202-66-0
Sumatriptanartificial5-(CH2SO2NHCH3)CH3CH31-[3-(2-Dimethylaminoethyl)-1''H''-indol-5-yl]-N-methyl-methanesulfonamide103628-46-2
Zolmitriptanartificial5-(CHNHC=OOCH2)CH3CH35-(4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine139264-17-8
artificial6-F CH3 CH3 6-fluoro-N,N-dimethyltryptamine 1511-31-5
6-Fluoro-DET[16] artificial6-F CH2CH3 CH2CH3 6-fluoro-N,N-diethyltryptamine 2836-69-3
6-Chloro-DMT artificial6-Cl CH3 CH3 6-chloro-N,N-dimethyltryptamine 25390-72-1
6-Methyl-DMT artificial6-CH3 CH3 CH3 6,N,N-trimethyltryptamine
6-Hydroxy-DMT artificial6-OH CH3 CH3 6-hydroxy-N,N-dimethyltryptamine 1476-33-1
6-Hydroxy-DET artificial6-OH CH3 CH3 6-hydroxy-N,N-diethyltryptamine 1476-59-1
6-Methoxy-DMT artificial6-OCH3 CH3 CH3 6-methoxy-N,N-dimethyltryptamine 2426-88-2
artificial7-CH3 CH3 CH3 7,N,N-trimethyltryptamine 65882-39-5
7-Ethyl-DMT artificial7-CH2CH3 CH3 CH3 7-ethyl-N,N-dimethyltryptamine
7-Chloro-DMT artificial7-Cl CH3 CH3 7-chloro-N,N-dimethyltryptamine
7-Bromo-DMT[17] artificial7-Br CH3 CH3 7-bromo-N,N-dimethyltryptamine 74798-68-8
7-Methoxy-DMT artificial7-OCH3 CH3 CH3 7-methoxy-N,N-dimethyltryptamine
7-Methoxy-MiPT artificial7-OCH3 CH3 CH(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
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-Fluoropsilocin artificial4-OH,6-F CH3 CH3 4-hydroxy-6-fluoro-N,N-dimethyltryptamine 312314-12-8
6-Fluoro-5-MeO-DMT artificial5-OCH3,6-F CH3 CH3 5-methoxy-6-fluoro-N,N-dimethyltryptamine
5,6-Difluoro-EPT artificial5-F, 6-F CH2CH3 CH2CH2CH3 5,6-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-Methoxy-7,N,N-trimethyltryptamineartificial5-OCH3, 7-CH3CH3CH35-Methoxy-7,N,N-trimethyltryptamine61018-77-7
5-Methoxy-4,N,N-trimethyltryptamineartificial4-CH3, 5-OCH3 CH3CH35-Methoxy-4,N,N-trimethyltryptamine
4-HO-5-MeO-DMTartificial4-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-methoxy-7-fluoro-METartificial5-OCH3, 7-FCH3CH2CH35-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
EMDTartificial2-CH2CH3, 5-OCH3CH3CH32-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine263744-72-5
ST-1936artificial2-CH3, 5-ClCH3CH32-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine1210-81-7
O-4310artificial1-CH(CH3)2, 4-OH, 6-FCH3CH33-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol885671-63-6
CP-132,484artificial1-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[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 (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-(2''H'',6''H''-[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-(2''H'',5''H''-[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-(2''H'',5''H''-[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. This is analogous to α-methylation of phenethylamine into amphetamine.

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. 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. 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
Tryptophan(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid73-22-3
5-Hydroxytryptophan2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid4350-09-8
αMT1-(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-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-dihydropyrano-αMT)(S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-''e'']indole362603-40-5
Compound 5 [27] 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-1''H''-indol-3-yl)propan-2-yl](methyl)amine4822-13-3
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
αMDiPT(2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
MPMI[28] 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole143321-54-4
Lucigenol(R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole250672-65-2
5-MeO-MPMI5-Methoxy-3--1H-indole143321-57-7
5F-MPMI[29] (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--5-[2-(benzenesulfonyl)ethyl]-1H-indole143322-58-1
Z5247692566[30] 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine

Related compounds

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
Dimemebfe2-(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
Mebfap3-(2-aminopropyl)-5-methoxybenzofuran140853-59-4
Ro60-0175(S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine169675-09-6
AAZ-A-154(2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine
Example 16 [31] [32] 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
Example 1 [33] 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-346621-((S)-2-Aminopropyl)-1H-indazol-6-ol210580-75-9
O-methyl-AL-346621-((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 [34] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine478132-12-6
Example 3 [35] (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine890087-75-9
Example 1 [36] (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine 1373917-69-1
YM-348(2S)-1-(7-ethyl-1H-furo[2,3-''g'']indazol-1-yl)propan-2-amine372163-84-3
2-desethyl-YM-348 [37] (2S)-1-(1H-furo[2,3-''g'']indazol-1-yl)propan-2-amine748116-94-1
I-32 [38] 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
2-Azapsilocin (Psilocin indazole analogue, P-6)[39] 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
VU6067416[40] 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole
(R)-693-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine
SN-223-(1-methylpiperidin-4-yl)-1H-indole17403-07-5

Further reading

See also

Notes and References

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