Substituted tryptamine

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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.

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[edit]

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 [1] 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
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 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 [2] artificial 4-OH CH3 H2C=CH-CH2 4-hydroxy-N-Methyl-N-allyltryptamine
4-AcO-MALT structure.png 4-AcO-MALT [3] 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 [4] 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-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
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-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 [5] 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 [6] 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 [7] 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
5-F-DiPT structure.png 5-Fluoro-DiPT artificial 5-F CH(CH3)2 CH(CH3)2 5-fluoro-N,N-diisoproptryptamine
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-NO2-DMT structure.png 5-Nitro-DMT artificial 5-NO2 CH3 CH3 5-nitro-N,N-dimethyltryptamine 69937-13-9
5-CN-DMT structure.png 5-Cyano-DMT artificial 5-C≡N CH3 CH3 5-cyano-N,N-dimethyltryptamine 17380-42-6
5-CN-DPT structure.png 5-Cyano-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[8] 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[9] 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
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
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
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[edit]

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.[10][11][12] 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.[12] This is analogous to α-methylation of phenethylamine into amphetamine.[12]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[13][14][15][16] and produce psychostimulant, entactogen, and/or psychedelic effects.[10][11][12] 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.[11][12] 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.[17]

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 [18] 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[19] 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
5F-MPMI structure.png 5-F-MPMI 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[edit]

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 [20] 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 [21] (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine 478132-12-6
US7425572-3 structure.png Example 3 [22] (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 [23] (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 [24] (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine 748116-94-1

Further reading[edit]

See also[edit]

References[edit]

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  2. ^ 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
  3. ^ 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
  4. ^ KOZIKOWSKI, Alan. SHAPIRO, Gideon. TUECKMANTEL, Werner. MCCORVY, John. 3-(2-(AMINOETHYL)-INDOL-4-OL DERIVATIVES, METHODS OF PREPARATION THEREOF, AND THE USE AS 5-HT2 RECEPTOR MODULATORS. Patent WO 2021/179091
  5. ^ Stamets PE. Tryptamine Compositions for Enhancing Neurite Outgrowth. WO 2021/101926
  6. ^ Kruegel AC, Sporn J. Specific Tryptamines for use in the Treatment of Mood Disorders. WO 2021/168082
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  8. ^ 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.
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  12. ^ a b c d e Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 641–. ISBN 978-1-60913-345-0.
  13. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  14. ^ Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  15. ^ Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin. 30 (12): 2328–33. doi:10.1248/bpb.30.2328. PMID 18057721.
  16. ^ Feldman JM, Chapman B (December 1975). "Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insluin secretion". Diabetologia. 11 (6): 487–94. doi:10.1007/bf01222097. PMID 1107123.
  17. ^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology. 200 (1): 187–90. doi:10.1016/0014-2999(91)90686-K. PMID 1722753.
  18. ^ Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorganic & Medicinal Chemistry Letters. 12 (2): 155–8. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343.
  19. ^ Macor JE, Wythes MJ. Indole derivatives. US patent 5607951
  20. ^ US granted 7012090, Chen HH, May JA, "Pyranoindoles for treating glaucoma", published 17 March 2000, issued 14 March 2006, assigned to Alcon, Inc. 
  21. ^ US granted 6881749, Chen HH, May JA, Severns BS, "Pyranoindazoles and their use for the treatment of glaucoma", published 3 June 2004, issued 19 April 2005, assigned to Alcon, Inc. 
  22. ^ US granted 7425572, Chen HH, May JA, "Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma", published 8 June 2006, issued 16 September 2008, assigned to Alcon, Inc. 
  23. ^ US granted 7268131, Dantanarayana AP, May JA, "Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma", published 15 December 2005, issued 11 September 2007, assigned to Alcon, Inc. 
  24. ^ Shimada I, Maeno K, Kazuta K, Kubota H, Kimizuka T, Kimura Y, et al. (February 2008). "Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists". Bioorganic & Medicinal Chemistry. 16 (4): 1966–82. doi:10.1016/j.bmc.2007.10.100. PMID 18035544.