The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN1=RN2=Rα = H.
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.

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

This list is incomplete; you can help by adding missing items. (October 2021)
Selected tryptamines
Chemical structure Short Name Origin Ring Substitution RN1 RN2 Full Name CAS Number
Tryptamine structure.svg
Tryptamine Animals, plants, fungi H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine 61-54-1
NMT structure.svg
NMT Plants H H CH3 N-methyltryptamine 61-49-4
2-Hydroxy-NMT.svg
2-HO-NMT Plants 2-OH H CH3 2-hydroxy-N-methyltryptamine 106987-89-7
5-MeO-NMT.svg
5-MeO-NMT Plants 5-OCH3 H CH3 5-methoxy-N-methyltryptamine 2009-03-2
Serotonin-2D-skeletal.svg
Serotonin Animals, plants 5-OH H H 5-hydroxytryptamine 50-67-9
Norbufotenine.svg
Nω-Methylserotonin (norbufotenin) Plants 5-OH H CH3 5-hydroxy-N-methyltryptamine 1134-01-6
Bufotenin2DACS.svg
Bufotenin Animals, plants, fungi 5-OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine 487-93-4
Bufotenidine.png
Bufotenidine Amphibians 5-O− (CH3)3 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate 487-91-2
Melatonin.svg
Melatonin Animals, plants, microbes 5-OCH3 H O=C-CH3 5-methoxy-N-acetyltryptamine 73-31-4
N-Acetylserotonin.png
N-Acetylserotonin Animals 5-OH H O=C-CH3 5-hydroxy-N-acetyltryptamine 1210-83-9
6-Hydroxymelatonin structure.svg
6-Hydroxymelatonin Animals 5-OCH3, 6-OH H O=C-CH3 N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide 2208-41-5
Norpsilocin.svg
4-HO-NMT Fungi 4-OH H CH3 4-hydroxy-N-methyltryptamine 28363-70-4
Psilocin.svg
Psilocin Fungi 4-OH CH3 CH3 4-hydroxy-N,N-dimethyltryptamine 520-53-6
Norbaeocystin.svg
Norbaeocystin Fungi 4-OPO3H2 H H 4-phosphoryloxy-tryptamine 21420-59-7
Baeocystin Formula V.1.svg
Baeocystin Fungi 4-OPO3H2 H CH3 4-phosphoryloxy-N-methyl-tryptamine 21420-58-6
Psilocybn.svg
Psilocybin Fungi 4-OPO3H2 CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine 520-52-5
Aeruginascin.png
Aeruginascin Fungi 4-OPO3H2 (CH3)3 [3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate 114264-95-8
DMT.svg
DMT Animals, plants H CH3 CH3 N,N-dimethyltryptamine 61-50-7
Lespedamine.svg
Lespedamine Plants 1-OCH3 CH3 CH3 1-methoxy-N,N-dimethyltryptamine 4335-93-7
5-MeO-DMT.svg
5-MeO-DMT Animals, plants 5-OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine 1019-45-0
5-Bromo-DMT.svg
5-Bromo-DMT Marine sponges, invertebrates 5-Br CH3 CH3 5-bromo-N,N-dimethyltryptamine 17274-65-6
6-Br-T.svg
6-Bromotryptamine Marine invertebrates 6-Br H H 6-bromotryptamine 96624-18-9
5,6 diBr-T.svg
5,6-Dibromotryptamine Marine invertebrates 5,6-Br H H 5,6-dibromotryptamine
5,6 diBr-NMT.svg
5,6-Dibromo-NMT Marine invertebrates 5,6-Br H CH3 5,6-dibromo-N-methyltryptamine
5,6-dibromo-DMT.svg
5,6-Dibromo-DMT Marine sponges, invertebrates 5,6-Br CH3 CH3 5,6-dibromo-N,N-dimethyltryptamine 72853-80-6
Desformylflustrabromine.svg
Desformylflustrabromine Marine invertebrates 2-(α,α-dimethylallyl), 6-Br H CH3 2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine 474657-72-2
Convolutindole A.svg
Convolutindole A Marine invertebrates 2,4,6-Br, 1,7-OCH3 CH3 CH3 1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine 443356-86-3
Acetryptine.svg
Acetryptine artificial 5-COCH3 H H 5-Acetyltryptamine 3551-18-6
5-benzyloxytryptamine.png
5-BT artificial 5-OCH2C6H5 H H 5-Benzyloxytryptamine 20776-45-8
5-Carboxamidotryptamine.svg
5-CT artificial 5-CONH2 H H 5-Carboxamidotryptamine 74885-09-9
5-Nonyloxytryptamine.svg
5-(Nonyloxy)tryptamine artificial 5-O(CH2)8CH3 H H 5-nonyloxytryptamine 157798-12-4
2-Methyl-5-hydroxytryptamine.svg
2-Methyl-5-hydroxytryptamine artificial 2-CH3, 5-OH H H 3-(2-aminoethyl)-2-methyl-1H-indol-5-ol 78263-90-8
N-Ethyltryptamine.png
NET artificial H H CH2CH3 N-ethyltryptamine 61-53-0
NiPT structure.png
NiPT artificial H H CH(CH3)2 N-isopropyltryptamine 14121-10-9
NcPT structure.png
NcPT artificial H H C3H5 N-cyclopropyltryptamine
NSBT structure.png
NSBT artificial H H CH(CH3)CH2CH3 N-sec-butyltryptamine
N-t-butyltryptamine.svg
NTBT artificial H H C(CH3)3 N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine
5MT-NBOMe structure.png
5-MT-NBOMe artificial 5-OCH3 H CH2C6H4(o-OCH3) 5-methoxy-N-(ortho-methoxybenzyl)tryptamine 1335331-37-7
5MT-NB3OMe structure.png
5-MT-NB3OMe [2] artificial 5-OCH3 H CH2C6H4(m-OCH3) 5-methoxy-N-(meta-methoxybenzyl)tryptamine 1648553-42-7
5-Methoxy-N-(4-bromobenzyl)tryptamine).svg
5-MeO-NBpBrT artificial 5-OCH3 H CH2C6H4(p-Br) N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine 155639-13-7
5-MeO-34MPEMT structure.png
5-MeO-34MPEMT [3] artificial 5-OCH3 CH3 CH2CH2C6H3(p,m-OCH3) N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine
Lu-AE58054.svg
Idalopirdine artificial 6-F H CH2C6H4(m-OCH2CF2CF2H) 2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoropropoxy)benzyl)ethanamine 467459-31-0
Pyr-T.png
Pyr-T artificial H (CH2)4 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole 14008-96-9
4-HO-pyr-T.png
4-HO-pyr-T artificial 4-OH (CH2)4 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol 63097-26-7
5-MeO-pyr-T.png
5-MeO-pyr-T artificial 5-OCH3 (CH2)4 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole 3949-14-2
MET image.svg
MET artificial H CH3 CH2CH3 N-Methyl-N-ethyltryptamine 5599-69-9
MPT structure.png
MPT artificial H CH3 CH2CH2CH3 N-Methyl-N-propyltryptamine 850032-72-3
MIPT.svg
MiPT artificial H CH3 CH(CH3)2 N-Methyl-N-isopropyltryptamine 96096-52-5
McPT structure.png
McPT artificial H CH3 C3H5 N-Methyl-N-cyclopropyltryptamine 1373918-63-8
EcPT structure.png
EcPT artificial H CH2CH3 C3H5 N-ethyl-N-cyclopropyltryptamine
PcPT structure.png
PcPT artificial H CH2CH2CH3 C3H5 N-propyl-N-cyclopropyltryptamine
IPcPT structure.png
iPcPT artificial H CH(CH3)2 C3H5 N-isopropyl-N-cyclopropyltryptamine
DcPT structure.png
DcPT artificial H C3H5 C3H5 N,N-dicyclopropyltryptamine 1373918-62-7
Methylbutyltryptamine.svg
MBT artificial H CH3 (CH2)3CH3 N-Methyl-N-butyltryptamine 848130-12-1
MSBT structure.png
MSBT artificial H CH3 CH(CH3)CH2CH3 N-Methyl-N-sec-butyltryptamine
MiBT structure.png
MiBT artificial H CH3 CH2CH(CH3)2 N-Methyl-N-iso-butyltryptamine
McPMT structure.png
McPMT artificial H CH3 CH2C3H5 N-Methyl-N-(cyclopropylmethyl)tryptamine
Diethyltryptamine.svg
DET artificial H CH2CH3 CH2CH3 N,N-diethyltryptamine 61-51-8
Ethylpropyltryptamine.svg
EPT artificial H CH2CH3 CH2CH2CH3 N-Ethyl-N-propyltryptamine 850032-68-7
Ethylisopropyltryptamine.svg
EiPT artificial H CH2CH3 CH(CH3)2 N-Ethyl-N-isopropyltryptamine 848130-11-0
DPT.svg
DPT artificial H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine 61-52-9
Propylisopropyltryptamine.svg
PiPT artificial H CH2CH2CH3 CH(CH3)2 N-Propyl-N-isopropyltryptamine 1354632-00-0
DiPT.svg
DiPT artificial H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine 14780-24-6
EBT structure.png
EBT artificial H CH2CH3 (CH2)3CH3 N-ethyl-N-butyltryptamine
PBT structure.png
PBT artificial H CH2CH2CH3 (CH2)3CH3 N-propyl-N-butyltryptamine
IPsBT structure.png
iPsBT artificial H CH(CH3)2 CH(CH3)CH2CH3 N-isopropyl-N-sec-butyltryptamine
Dibutyltryptamine.svg
DBT artificial H (CH2)3CH3 (CH2)3CH3 N,N-dibutyltryptamine 15741-77-2
DIBT structure.png
DIBT artificial H CH2CH(CH3)2 CH2CH(CH3)2 N,N-diisobutyltryptamine 63938-64-7
DSBT structure.png
DSBT artificial H CH(CH3)CH2CH3 CH(CH3)CH2CH3 N,N-disecbutyltryptamine
Methylallyltryptamine.svg
MALT artificial H CH3 H2C=CH-CH2 N-methyl-N-allyltryptamine 1366416-29-6
DALT-structure.png
DALT artificial H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine 60676-77-9
ALiPT structure.png
ALiPT artificial H H2C=CH-CH2 CH(CH3)2 N-allyl-N-isopropyltryptamine
2-Me-DMT.svg
2-Methyl-DMT artificial 2-CH3 CH3 CH3 (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine 1080-95-1
2-methyl-diethyltryptamine.png
2-Me-DET artificial 2-CH3 CH2CH3 CH2CH3 N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine 26628-88-6
4-Amino-DMT structure.png
4-Amino-DMT [4] artificial 4-NH2 CH3 CH3 4-amino-N,N-dimethyltryptamine 60331-61-5
4-Me-DMT structure.png
4-Methyl-DMT artificial 4-CH3 CH3 CH3 4,N,N-trimethyltryptamine 28289-23-8
4-MeO-DMT.png
4-MeO-DMT artificial 4-OCH3 CH3 CH3 4-methoxy-N,N-dimethyltryptamine 3965-97-7
4-MeO-MiPT.png
4-MeO-MiPT artificial 4-OCH3 CH3 CH(CH3)2 4-methoxy-N-methyl-N-isopropyltryptamine 96096-53-6
4-MeO-DiPT structure.png
4-MeO-DiPT artificial 4-OCH3 CH(CH3)2 CH(CH3)2 4-methoxy-N,N-diisopropyltryptamine
O-Acetylpsilocin chemical structure.png
4-AcO-DMT artificial 4-OCOCH3 CH3 CH3 4-acetoxy-N,N-dimethyltryptamine 92292-84-7
4-PrO-DMT.svg
4-PrO-DMT artificial 4-OCOCH2CH3 CH3 CH3 4-propionyloxy-N,N-dimethyltryptamine 1373882-11-1
4-HO-MET.svg
4-HO-MET artificial 4-OH CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine 77872-41-4
4-Acetoxy-N-methyl-N-ethyltryptamine.svg
4-Acetoxy-MET artificial 4-OCOCH3 CH3 CH2CH3 4-acetoxy-N-methyl-N-ethyltryptamine 1445751-40-5
4-PO-MET structure.png
4-PO-MET artificial 4-OPO3H2 CH3 CH2CH3 4-phosphoryloxy-N-methyl-N-ethyltryptamine
4-HO-DET.svg
4-HO-DET artificial 4-OH CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine 22204-89-3
4-Acetoxy-DET.png
4-Acetoxy-DET artificial 4-OCOCH3 CH2CH3 CH2CH3 4-acetoxy-N,N-diethyltryptamine 1135424-15-5
Ethocybin.png
4-PO-DET artificial 4-OPO3H2 CH2CH3 CH2CH3 4-phosphoryloxy-N,N-diethyltryptamine 60480-02-6
4-Hydroxy-N-ethyl-N-propyltryptamine.svg
4-HO-EPT artificial 4-OH CH2CH3 CH2CH2CH3 4-hydroxy-N-ethyl-N-propyltryptamine 2595431-59-5
4-PO-EPT structure.png
4-PO-EPT artificial 4-OPO3H2 CH2CH3 CH2CH2CH3 4-phosphoryloxy-N-ethyl-N-propyltryptamine
4-AcO-EiPT Structure.svg
4-AcO-EiPT artificial 4-OCOCH3 CH2CH3 CH(CH3)2 4-acetoxy-N-ethyl-N-isopropyltryptamine
4-HO-MPT.svg
4-HO-MPT artificial 4-OH CH3 CH2CH2CH3 4-hydroxy-N-methyl-N-propyltryptamine 763035-03-6
4-HO-MiPT.svg
4-HO-MiPT artificial 4-OH CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine 77872-43-6
4-Acetoxy-MiPT.svg
4-Acetoxy-MiPT artificial 4-OCOCH3 CH3 CH(CH3)2 4-acetoxy-N-methyl-N-isopropyltryptamine 1024612-25-6
4-HO-MALT structure.png
4-HO-MALT[5] artificial 4-OH CH3 H2C=CH-CH2 4-hydroxy-N-Methyl-N-allyltryptamine
4-AcO-MALT structure.png
4-AcO-MALT [6] artificial 4-OCOCH3 CH3 H2C=CH-CH2 4-acetoxy-N-Methyl-N-allyltryptamine
4-HO-MSBT structure.png
4-HO-MSBT artificial 4-OH CH(CH3)CH2CH3 CH3 4-hydroxy-N-sec-butyl-N-methyltryptamine
4-HO-McPT.svg
4-HO-McPT artificial 4-OH C3H5 CH3 4-hydroxy-N-cyclopropyl-N-methyltryptamine
4-HO-McPeT.svg
4-HO-McPeT artificial 4-OH C5H9 CH3 4-hydroxy-N-cyclopentyl-N-methyltryptamine 77872-48-1
4-OH-McPMT structure.png
4-HO-McPMT [7] artificial 4-OH CH2C3H5 CH3 4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
4-HO-DPT.svg
4-HO-DPT artificial 4-OH CH2CH2CH3 CH2CH2CH3 4-hydroxy-N,N-dipropyltryptamine 63065-88-3
4-AcO-DPT Structure.svg
4-AcO-DPT artificial 4-OCOCH3 CH2CH2CH3 CH2CH2CH3 4-acetoxy-N,N-dipropyltryptamine 1445751-75-6
4-HO-PiPT structure.png
4-HO-PiPT artificial 4-OH CH2CH2CH3 CH(CH3)2 4-hydroxy-N-propyl-N-isopropyltryptamine
4-AcO-PiPT structure.png
4-AcO-PiPT artificial 4-OCOCH3 CH2CH2CH3 CH(CH3)2 4-acetoxy-N-propyl-N-isopropyltryptamine
4-HO-DIPT.SVG
4-HO-DIPT artificial 4-OH CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine 132328-45-1
4-AcO-DiPT.svg
4-Acetoxy-DiPT artificial 4-OCOCH3 CH(CH3)2 CH(CH3)2 4-acetoxy-N,N-diisopropyltryptamine 936015-60-0
4-PrO-DiPT structure.png
4-PrO-DiPT artificial 4-OCOCH2CH3 CH(CH3)2 CH(CH3)2 4-propionyloxy-N,N-diisopropyltryptamine 1373882-13-3
FT-104 structure.png
FT-104 artificial 4-OCO(CH2)3COOH CH(CH3)2 CH(CH3)2 4-glutaryloxy-N,N-diisopropyltryptamine
4-PO-DiPT structure.png
4-PO-DiPT artificial 4-OPO3H2 CH(CH3)2 CH(CH3)2 4-phosphoryloxy-N,N-diisopropyltryptamine 1373882-09-7
4-HO-DALT structure.png
4-HO-DALT artificial 4-OH H2C=CH-CH2 H2C=CH-CH2 4-hydroxy-N,N-diallyltryptamine
4-AcO-DALT.svg
4-AcO-DALT artificial 4-OCOCH3 H2C=CH-CH2 H2C=CH-CH2 4-acetoxy-N,N-diallyltryptamine 1445751-71-2
4-HO-DBT.svg
4-HO-DBT artificial 4-OH (CH2)3CH3 (CH2)3CH3 4-hydroxy-N,N-dibutyltryptamine 63065-89-4
4-HO-DIBT structure.png
4-HO-DIBT artificial 4-OH CH2CH(CH3)2 CH2CH(CH3)2 4-hydroxy-N,N-diisobutyltryptamine
4-HO-DSBT.svg
4-HO-DSBT artificial 4-OH CH(CH3)CH2CH3 CH(CH3)CH2CH3 4-hydroxy-N,N-disecbutyltryptamine 127507-01-1
5-MeO-MET.svg
5-MeO-MET artificial 5-OCH3 CH2CH3 CH3 5-methoxy-N-Methyl-N-ethyltryptamine 16977-53-0
5-MeO-DET.svg
5-MeO-DET artificial 5-OCH3 CH2CH3 CH2CH3 5-methoxy-N,N-diethyltryptamine 2454-70-8
5-MeO-MPT structure.png
5-MeO-MPT artificial 5-OCH3 CH3 CH2CH2CH3 5-methoxy-N-methyl-N-propyltryptamine
5-MeO-EPT.svg
5-MeO-EPT artificial 5-OCH3 CH2CH3 CH2CH2CH3 5-methoxy-N-ethyl-N-propyltryptamine 850032-67-6
5-MeO-DPT.svg
5-MeO-DPT artificial 5-OCH3 CH2CH2CH3 CH2CH2CH3 5-methoxy-N,N-dipropyltryptamine 69496-75-9
5-MeO-MALT.png
5-MeO-MALT artificial 5-OCH3 H2C=CH-CH2 CH3 5-methoxy-N-Methyl-N-allyltryptamine 1373918-64-9
5-MeO-DALT.svg
5-MeO-DALT artificial 5-OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine 928822-98-4
5-MeO-ALiPT structure.png
5-MeO-ALiPT artificial 5-OCH3 H2C=CH-CH2 CH2CH(CH3)2 5-methoxy-N-allyl-N-isopropyltryptamine
5-MeO-MiPT.svg
5-MeO-MiPT artificial 5-OCH3 CH3 CH(CH3)2 5-methoxy-N,N-methylisopropyltryptamine 96096-55-8
5,6-MeO-MiPT.svg
5,6-MeO-MiPT artificial 5-OCH3, 6-OCH3 CH3 CH(CH3)2 5,6-dimethoxy-N,N-methylisopropyltryptamine
5-MeO-McPT structure.png
5-MeO-McPT artificial 5-OCH3 CH3 C3H5 5-methoxy-N-methyl-N-cyclopropyltryptamine
5-MeO-EiPT structure.png
5-MeO-EiPT artificial 5-OCH3 CH2CH3 CH(CH3)2 5-methoxy-N-ethyl-N-isopropyltryptamine 850032-66-5
5-MeO-PiPT structure.png
5-MeO-PiPT artificial 5-OCH3 CH2CH2CH3 CH(CH3)2 5-methoxy-N-propyl-N-isopropyltryptamine
5-MeO-DiPT.svg
5-MeO-DIPT artificial 5-OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine 4021-34-5
5-MeO-DBT.svg
5-MeO-DBT artificial 5-OCH3 (CH2)3CH3 (CH2)3CH3 5-methoxy-N,N-dibutyltryptamine 73785-42-9
5-MeO-DsBT structure.png
5-MeO-DSBT artificial 5-OCH3 CH(CH3)CH2CH3 CH(CH3)CH2CH3 5-methoxy-N,N-di-sec-butyltryptamine
5-MeS-DMT.svg
5-MeS-DMT artificial 5-SCH3 CH3 CH3 5-methylthio-N,N-dimethyltryptamine 5102-11-4
5-AcO-DMT.svg
5-AcO-DMT artificial 5-OCOCH3 CH3 CH3 5-acetoxy-N,N-dimethyltryptamine 16977-50-7
5-AcO-MET structure.png
5-AcO-MET [8] artificial 5-OCOCH3 CH3 CH2CH3 5-acetoxy-N-methyl-N-ethyltryptamine
5-AcO-DET structure.png
5-AcO-DET artificial 5-OCOCH3 CH2CH3 CH2CH3 5-acetoxy-N,N-diethyltryptamine
5-AcO-EPT structure.png
5-AcO-EPT [9] artificial 5-OCOCH3 CH2CH3 CH2CH2CH3 5-acetoxy-N-ethyl-N-propyltryptamine
5-AcO-DPT structure.png
5-AcO-DPT artificial 5-OCOCH3 CH2CH2CH3 CH2CH2CH3 5-acetoxy-N,N-dipropyltryptamine
5-AcO-MiPT structure.png
5-AcO-MiPT artificial 5-OCOCH3 CH3 CH(CH3)2 5-acetoxy-N-methyl-N-isopropyltryptamine
5-AcO-DiPT structure.png
5-AcO-DiPT artificial 5-OCOCH3 CH(CH3)2 CH(CH3)2 5-acetoxy-N,N-diisopropyltryptamine
5-EtO-DMT Structure.svg
5-Ethoxy-DMT artificial 5-OCH2CH3 CH3 CH3 5-ethoxy-N,N-dimethyltryptamine 855245-09-9
5-EtO-MET structure.png
5-Ethoxy-MET artificial 5-OCH2CH3 CH3 CH2CH3 5-ethoxy-N-methyl-N-ethyltryptamine
5-EtO-DET structure.png
5-Ethoxy-DET artificial 5-OCH2CH3 CH2CH3 CH2CH3 5-ethoxy-N,N-diethyltryptamine
5-EtO-MPT structure.png
5-Ethoxy-MPT artificial 5-OCH2CH3 CH3 CH2CH2CH3 5-ethoxy-N-methyl-N-propyltryptamine
5-EtO-EPT structure.png
5-Ethoxy-EPT artificial 5-OCH2CH3 CH2CH3 CH2CH2CH3 5-ethoxy-N-ethyl-N-propyltryptamine
5-EtO-DPT structure.png
5-Ethoxy-DPT artificial 5-OCH2CH3 CH2CH2CH3 CH2CH3 5-ethoxy-N,N-dipropyltryptamine
5-EtO-MiPT structure.png
5-Ethoxy-MiPT artificial 5-OCH2CH3 CH3 CH(CH3)2 5-ethoxy-N-methyl-N-isopropyltryptamine
5-EtO-EiPT structure.png
5-Ethoxy-EiPT artificial 5-OCH2CH3 CH2CH3 CH(CH3)2 5-ethoxy-N-ethyl-N-isopropyltryptamine
5-EtO-DiPT structure.png
5-Ethoxy-DiPT artificial 5-OCH2CH3 CH(CH3)2 CH(CH3)2 5-ethoxy-N,N-diisopropyltryptamine
5-EtO-DALT structure.png
5-Ethoxy-DALT artificial 5-OCH2CH3 H2C=CH-CH2 H2C=CH-CH2 5-ethoxy-N,N-diallyltryptamine
5-BnO-DMT structure.png
5-BnO-DMT artificial 5-OCH2C6H5 CH3 CH3 5-benzyloxy-N,N-dimethyltryptamine 101832-88-6
5-OH-DET structure.png
5-HO-DET artificial 5-OH CH2CH3 CH2CH3 5-hydroxy-N,N-diethyltryptamine 14009-42-8
5-OH-DPT structure.png
5-HO-DPT artificial 5-OH CH2CH2CH3 CH2CH2CH3 5-hydroxy-N,N-dipropyltryptamine 36288-75-2
5-OH-MiPT structure.png
5-HO-MiPT artificial 5-OH CH3 CH(CH3)2 5-hydroxy-N-methyl-N-isopropyltryptamine
5-HO-DiPT.svg
5-HO-DiPT artificial 5-OH CH(CH3)2 CH(CH3)2 5-hydroxy-N,N-diisopropyltryptamine 36288-76-3
5,N,N-TMT.svg
5-Methyl-DMT (5,N,N-TMT) artificial 5-CH3 CH3 CH3 5,N,N-trimethyltryptamine 22120-39-4
5-Ethyl-DMT structure.svg
5-Ethyl-DMT artificial 5-CH2CH3 CH3 CH3 5-ethyl-N,N-dimethyltryptamine 171783-25-8
5-iPr-DMT structure.png
5-Isopropyl-DMT artificial 5-CH(CH3)2 CH3 CH3 5-isopropyl-N,N-dimethyltryptamine 156281-04-8
5-tBu-DMT structure.png
5-(t-Butyl)-DMT [10] artificial 5-C(CH3)3 CH3 CH3 5-(tert-butyl)-N,N-dimethyltryptamine
5-Fluoro-DMT structure.png
5-Fluoro-DMT artificial 5-F CH3 CH3 5-fluoro-N,N-dimethyltryptamine 22120-36-1
5-F-MET.svg
5-Fluoro-MET artificial 5-F CH3 CH2CH3 5-fluoro-N-methyl-N-ethyltryptamine
5-Fluoro-DET.svg
5-Fluoro-DET artificial 5-F CH2CH3 CH2CH3 5-fluoro-N,N-diethyltryptamine
5-Fluoro-EPT.svg
5-Fluoro-EPT artificial 5-F CH2CH3 CH2CH2CH3 5-fluoro-N-ethyl-N-propyltryptamine
5-F-DPT structure.png
5-Fluoro-DPT artificial 5-F CH2CH2CH3 CH2CH2CH3 5-fluoro-N,N-dipropyltryptamine
5F-PiPT structure.png
5-Fluoro-PiPT artificial 5-F CH2CH2CH3 CH(CH3)2 5-fluoro-N-propyl-N-isopropyltryptamine
5F-PcBT structure.png
5-Fluoro-PcBT artificial 5-F CH2CH2CH3 CH(CH2)3 5-fluoro-N-propyl-N-cyclobutyltryptamine
5F-iPcBT structure.png
5-Fluoro-iPcBT artificial 5-F CH(CH3)2 CH(CH2)3 5-fluoro-N-isopropyl-N-cyclobutyltryptamine
5-F-DiPT structure.png
5-Fluoro-DiPT artificial 5-F CH(CH3)2 CH(CH3)2 5-fluoro-N,N-diisoproptryptamine
5F-sBALT structure.png
5-Fluoro-sBALT artificial 5-F CH(CH3)CH2CH3 CH2CH=CH2 5-fluoro-N-sec-butyl-N-allyltryptamine
5F-M1MALT structure.png
5-Fluoro-M1MALT artificial 5-F CH3 CH(CH3)CH=CH2 5-fluoro-N-methyl-N-(1-methylallyl)tryptamine
5-Chloro-DMT.svg
5-Chloro-DMT artificial 5-Cl CH3 CH3 5-chloro-N,N-dimethyltryptamine 22120-32-7
5-I-DMT structure.png
5-Iodo-DMT artificial 5-I CH3 CH3 5-iodo-N,N-dimethyltryptamine 22120-38-3
5-TFM-DMT structure.png
5-TFM-DMT artificial 5-CF3 CH3 CH3 5-(trifluoromethyl)-N,N-dimethyltryptamine 2418713-32-1
5-TFMO-DMT structure.png
5-TFMO-DMT[11] artificial 5-OCF3 CH3 CH3 5-(trifluoromethoxy)-N,N-dimethyltryptamine
5-NO2-DMT structure.png
5-Nitro-DMT[12] artificial 5-NO2 CH3 CH3 5-nitro-N,N-dimethyltryptamine 69937-13-9
5-CN-DMT structure.png
5-CN-DMT artificial 5-C≡N CH3 CH3 5-cyano-N,N-dimethyltryptamine 17380-42-6
5-CN-DPT structure.png
5-CN-DPT artificial 5-C≡N CH2CH2CH3 CH2CH2CH3 5-cyano-N,N-dipropyltryptamine 74885-19-1
Almotriptan skeletal.svg
Almotriptan artificial 5-(CH2SO2N(CH2)4) CH3 CH3 N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine 154323-57-6
Rizatriptan Structural Formula V.1.svg
Rizatriptan artificial 5-(CH2(N3(CH)2)) CH3 CH3 N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine 145202-66-0
Sumatriptan.svg
Sumatriptan artificial 5-(CH2SO2NHCH3) CH3 CH3 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide 103628-46-2
Zolmitriptan Structure V.1.svg
Zolmitriptan artificial 5-(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine 139264-17-8
6-Fluoro-DMT skeletal.svg
6-Fluoro-DMT artificial 6-F CH3 CH3 6-fluoro-N,N-dimethyltryptamine 1511-31-5
6-Fluoro-DET.svg
6-Fluoro-DET[13] artificial 6-F CH2CH3 CH2CH3 6-fluoro-N,N-diethyltryptamine 2836-69-3
6-Cl-DMT structure.png
6-Chloro-DMT artificial 6-Cl CH3 CH3 6-chloro-N,N-dimethyltryptamine 25390-72-1
6-Me-DMT structure.png
6-Methyl-DMT artificial 6-CH3 CH3 CH3 6,N,N-trimethyltryptamine
6-OH-DMT structure.png
6-Hydroxy-DMT artificial 6-OH CH3 CH3 6-hydroxy-N,N-dimethyltryptamine 1476-33-1
6-OH-DET structure.png
6-Hydroxy-DET artificial 6-OH CH3 CH3 6-hydroxy-N,N-diethyltryptamine 1476-59-1
6-MeO-DMT structure.png
6-Methoxy-DMT artificial 6-OCH3 CH3 CH3 6-methoxy-N,N-dimethyltryptamine 2426-88-2
7-TMT structure.png
7-Methyl-DMT artificial 7-CH3 CH3 CH3 7,N,N-trimethyltryptamine 65882-39-5
7-Et-DMT structure.png
7-Ethyl-DMT artificial 7-CH2CH3 CH3 CH3 7-ethyl-N,N-dimethyltryptamine
7-Cl-DMT structure.png
7-Chloro-DMT artificial 7-Cl CH3 CH3 7-chloro-N,N-dimethyltryptamine
7-Br-DMT structure.png
7-Bromo-DMT[14] artificial 7-Br CH3 CH3 7-bromo-N,N-dimethyltryptamine 74798-68-8
7-MeO-DMT structure.png
7-Methoxy-DMT artificial 7-OCH3 CH3 CH3 7-methoxy-N,N-dimethyltryptamine
7-MeO-MiPT structure.png
7-Methoxy-MiPT artificial 7-OCH3 CH3 CH(CH3)2 7-methoxy-N-methyl-N-isopropyltryptamine
1-Methylpsilocin.svg
1-Methylpsilocin artificial 1-CH3, 4-OH CH3 CH3 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole 1465-16-3
1-Me-5-MeO-DiPT.svg
1-Methyl-5-MeO-DiPT artificial 1-CH3, 5-OCH3 CH(CH3)2 CH(CH3)2 1-methyl-5-methoxy-N,N-diisopropyltryptamine 1373882-10-0
NB-5-MeO-MiPT structure.png
NB-5-MeO-MiPT artificial 1-OCOC(CH3)3, 5-OCH3 CH3 CH(CH3)2 1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
NB-5-MeO-DALT structure.png
NB-5-MeO-DALT artificial 1-OCOC(CH3)3, 5-OCH3 H2C=CH-CH2 H2C=CH-CH2 1-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine
6-Fluoropsilocin structure.png
6-Fluoropsilocin artificial 4-OH,6-F CH3 CH3 4-hydroxy-6-fluoro-N,N-dimethyltryptamine 312314-12-8
6F-5-MeO-DMT structure.png
6-Fluoro-5-MeO-DMT artificial 5-OCH3,6-F CH3 CH3 5-methoxy-6-fluoro-N,N-dimethyltryptamine
56DF-EPT structure.png
5,6-Difluoro-EPT artificial 5-F, 6-F CH2CH3 CH2CH2CH3 5,6-difluoro-N-ethyl-N-propyltryptamine
5-MeO-2,N,N-TMT.svg
5-MeO-2-TMT artificial 2-CH3, 5-OCH3 CH3 CH3 2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine 67292-68-6
5-MeO-7-TMT.png
5-Methoxy-7,N,N-trimethyltryptamine artificial 5-OCH3, 7-CH3 CH3 CH3 5-Methoxy-7,N,N-trimethyltryptamine 61018-77-7
5-MeO-4NN-TMT structure.png
5-Methoxy-4,N,N-trimethyltryptamine artificial 4-CH3, 5-OCH3 CH3 CH3 5-Methoxy-4,N,N-trimethyltryptamine
4-HO-5-MeO-DMT.svg
4-HO-5-MeO-DMT artificial 4-OH, 5-OCH3 CH3 CH3 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine 2433-31-0
4-Fluoro-5-methoxy-N,N-dimethyltryptamine.svg
4-F-5-MeO-DMT artificial 4-F, 5-OCH3 CH3 CH3 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine 312314-18-4
7F-5-MeO-MET structure.png
5-methoxy-7-fluoro-MET artificial 5-OCH3, 7-F CH3 CH2CH3 5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
EMDT structure.svg
EMDT artificial 2-CH2CH3, 5-OCH3 CH3 CH3 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine 263744-72-5
ST-1936 structure.svg
ST-1936 artificial 2-CH3, 5-Cl CH3 CH3 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine 1210-81-7
O-4310 structure.svg
O-4310 artificial 1-CH(CH3)2, 4-OH, 6-F CH3 CH3 3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol 885671-63-6
CP-132,484 Structure.svg
CP-132,484 artificial 1-methyl-4,5-(OCH2CH2CH2) H H 1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole 143508-76-3
4,5-DHP-DMT.svg
4,5-DHP-DMT artificial 4,5-(OCH2CH2CH2) CH3 CH3 1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole 135360-97-3
4,5-MDO-DMT.svg
4,5-MDO-DMT artificial 4,5-(OCH2O) CH3 CH3 2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine 81249-30-1
4,5-MDO-DiPT.svg
4,5-MDO-DiPT artificial 4,5-(OCH2O) CH(CH3)2 CH(CH3)2 N-[2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine 82173-82-8
5,6-MDO-DMT.svg
5,6-MDO-DMT artificial 5,6-(OCH2O) CH3 CH3 2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine
5,6-MDO-MiPT.svg
5,6-MDO-MiPT artificial 5,6-(OCH2O) CH3 CH(CH3)2 N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine
5,6-MDO-DiPT.svg
5,6-MDO-DiPT artificial 5,6-(OCH2O) CH(CH3)2 CH(CH3)2 N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine
Chemical Structure Short Name Origin Ring Substitution RN1 RN2 Full Name CAS 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.[15][16][17] 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.[17] This is analogous to α-methylation of phenethylamine into amphetamine.[17]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[18][19][20][21] and produce psychostimulant, entactogen, and/or psychedelic effects.[15][16][17] 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.[16][17] 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.[22]

Structure Common name Chemical name CAS number
L-Tryptophan - L-Tryptophan.svg
Tryptophan (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid 73-22-3
5-Hydroxy-L-Tryptophan (5-HTP).svg
5-Hydroxytryptophan 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid 4350-09-8
AMT.svg
αMT 1-(1H-Indol-3-yl)propan-2-amine 299-26-3
4-HO-aMT Structure.svg
4-HO-αMT 3-(2-aminopropyl)-1H-indol-4-ol 15066-09-8
4-Methyl-AMT.png
4-Methyl-αMT 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine 3569-29-7
5-fluoro-alpha-methyltryptamine.svg
5-Fluoro-αMT 1-(5-fluoro-1H-indol-3-yl)propan-2-amine 712-08-3
5-Chloro-3-(2-aminopropyl)indole.svg
5-Chloro-αMT 1-(5-Chloro-1H-indol-3-yl)propan-2-amine 712-07-2
5-HO-AMT structure.png
5-HO-αMT (αMS/α-methyl-5-HT) 3-(2-aminopropyl)-1H-indol-5-ol 304-52-9
5-MeO-AMT.svg
5-MeO-αMT 1-(5-methoxy-1H-indol-3-yl)propan-2-amine 1137-04-8
5EtO-AMT structure.png
5-Ethoxy-αMT 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine 101832-83-1
5-iPrO-AMT structure.png
5-Isopropoxy-αMT 1-{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-propanamine 160521-72-2
6-fluoro-AMT structure.png
6-Fluoro-αMT 1-(6-fluoro-1H-indol-3-yl)propan-2-amine 712-11-8
7-Cl-AMT structure.png
7-Chloro-AMT 1-(7-chloro-1H-indol-3-yl)propan-2-amine 711-99-9
AL-37350A structure.png
AL-37350A (4,5-dihydropyrano-αMT) (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole 362603-40-5
BIAP structure.png
Compound 5 [23] 1-(3H-benzo[e]indol-1-yl)propan-2-amine
AET.svg
αET 1-(1H-indol-3-yl)butan-2-amine 2235-90-7
4-Methyl-AET.png
4-Methyl-αET 1-(4-Methyl-1H-indol-3-yl)butan-2-amine 28289-30-7
4HO-AET structure.png
4-HO-αET 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine 28289-28-3
5F-AET structure.png
5-Fluoro-αET 1-(5-fluoro-1H-indol-3-yl)butan-2-amine 1380137-98-3
5Me-AET structure.png
5-Methyl-αET 1-(5-methyl-1H-indol-3-yl)butan-2-amine 1380148-21-9
5-MeO-AET.svg
5-MeO-αET 1-(5-methoxy-1H-indol-3-yl)butan-2-amine 4765-10-0
7-Methyl-AET.png
7-Methyl-αET 1-(7-methyl-1H-indol-3-yl)butan-2-amine 13712-80-6
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)amine 4822-13-3
Α,N,N-TMT.png
N,N-Dimethyl-αMT (α,N,N-TMT) (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine 4761-32-4
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)dimethylamine 101831-90-7
AMDIPT structure.png
αMDiPT (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
MPMI structure.png
MPMI[24] 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole 143321-54-4
4-HO-N-Me-TMT.png
Lucigenol (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole 250672-65-2
5-MeO-N-Me-TMT.svg
5-MeO-MPMI 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole 143321-57-7
R5F-MPMI structure.png
5F-MPMI[25] (R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole
5Br-MPMI structure.png
5-Br-MPMI 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole 143322-57-0
Eletriptan skeletal.svg
Eletriptan 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole 143322-58-1

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.

Structure Common name Chemical name CAS number
Dimemebfe.png
Dimemebfe 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine 140853-58-3
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-APB 3-(2-aminopropyl)benzofuran 105909-13-5
Mebfap structure.png
Mebfap 3-(2-aminopropyl)-5-methoxybenzofuran 140853-59-4
Ro60-0175 structure.png
Ro60-0175 (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine 169675-09-6
AAZ-A-154 structure.png
AAZ-A-154 (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine
US7012090-1 structure.png
Example 1 [26] 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-amine 259857-99-3
AL-34662 structure.png
AL-34662 1-((S)-2-Aminopropyl)-1H-indazol-6-ol 210580-75-9
O-methyl-AL34662 structure.png
O-methyl-AL-34662 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole 210580-60-2
7-methyl-AL34662 structure.png
7-methyl-AL-34662 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol 874668-67-4
7-chloro-AL34662 structure.png
7-chloro-AL-34662 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol 874881-86-4
AL-38022A structure.png
AL-38022A (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine 478132-11-5
US6881749-9 structure.png
Example 9 [27] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine 478132-12-6
US7425572-3 structure.png
Example 3 [28] (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine 890087-75-9
US7268131-1 structure.png
Example 1 [29] (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine 1373917-69-1
YM-348 structure.png
YM-348 (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine 372163-84-3
2-desethyl-YM348 structure.png
2-desethyl-YM-348 [30] (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine 748116-94-1
I-32 structure.png
I-32 [31] 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
R69 structure.png
(R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine

Further reading

See also

References

  1. ^ Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable". phys.org. Retrieved 2022-12-26.
  2. ^ Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK (2019). "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE. 14 (1): e0209804. Bibcode:2019PLoSO..1409804T. doi:10.1371/journal.pone.0209804. PMC 6328172. PMID 30629611.
  3. ^ Jensen N. Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. PhD thesis, University of Göttingen, 2004
  4. ^ McKay JB, Parkhurst RM, Silverstein RM, Skinner WA. Analogues of Psilocin and Lysergic acid diethylamide I. Chloro, Nitro, and Amino Derivatives of 3-Substituted Indoles. Canadian Journal of Chemistry. October 1963; 41(10): 2585-2590. doi:10.1139/v63-378
  5. ^ Klein AK, et al. Investigation of the Structure–Activity Relationships of Psilocybin Analogues. ACS Pharmacol. Transl. Sci. 2021; 4(2): 533–542. doi:10.1021/acsptsci.0c00176
  6. ^ Pham DNK, et al. Psilacetin derivatives: fumarate salts of the methyl–ethyl, methyl–allyl and diallyl variants of the psilocin prodrug. Acta Cryst. (2021). E77, 101-106. doi:10.1107/S2056989021000116
  7. ^ WO 2021179091, Kozikowski A, Shaprio G, Tueckmantel W, McCorvy J, "3-(2-(Aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-HT2 receptor modulators", published 16 September 2021, assigned to Bright Minds Biosciences Inc. and The Medical College Of Wisconsin Inc. 
  8. ^ WO 2021101926, Stamets PE, "Tryptamine Compositions for Enhancing Neurite Outgrowth.", published 2021-05-27, assigned to Stamets Paul Edward. 
  9. ^ WO 2021168082, Kruegel AC, Sporn J, "Specific Tryptamines for use in the Treatment of Mood Disorders.", published 26 August 2021 
  10. ^ Xu YC, Schaus JM, Walker C, Krushinski J, Adham N, Zgombick JM, Liang SX, Kohlman DT, Audia JE (February 1999). "N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist". Journal of Medicinal Chemistry. 42 (3): 526–31. doi:10.1021/jm9805945. PMID 9986723.
  11. ^ WO 2022235927, Kruegel AC, "Novel Tryptamines and Methods of Treating Mood Disorders", published 10 November 2022, assigned to Gilgamesh Pharmaceuticals, Inc. 
  12. ^ Shaw E, Woolley DW (April 1953). "The synthesis of nitro-and aminoindoles analogous to serotonin". Journal of the American Chemical Society. 75 (8): 1877–1881. doi:10.1021/ja01104a029.
  13. ^ Rabin RA, Regina M, Doat M, Winter JC (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior. 72 (1–2): 29–37. doi:10.1016/s0091-3057(01)00720-1. PMID 11900766. S2CID 6480715.
  14. ^ Glennon RA, Schubert E, Jacyno JM, Rosecrans JA (November 1980). "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry. 23 (11): 1222–6. doi:10.1021/jm00185a014. PMID 6779006.
  15. ^ a b Ries RK, Miller SC, Fiellin DA (2009). Principles of Addiction Medicine. Lippincott Williams & Wilkins. pp. 216–218. ISBN 978-0-7817-7477-2.
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