Замещенный триптамин
Class of indoles
Структура замещенных триптаминов. Сам триптамин получается при R4=R5=RN 1 =RN 2 =Rα = H.
Структура замещенных триптаминов со всеми помеченными позициями.

Замещенные триптамины , или просто триптамины , также известные как аналоги серотонина (т. е. аналоги 5-гидрокситриптамина ), представляют собой органические соединения , которые можно считать производными от самого триптамина . Молекулярные структуры всех триптаминов содержат индольное кольцо, соединенное с аминогруппой (NH 2 ) через этиловую (−CH2–CH2−) боковую цепь . В замещенных триптаминах индольное кольцо, боковая цепь и/или аминогруппа модифицированы путем замены одного из атомов водорода (H) другой группой.

Известные триптамины включают серотонин , важный нейромедиатор , и мелатонин , гормон, участвующий в регуляции цикла сна и бодрствования. Триптаминовые алкалоиды встречаются в грибах , растениях и животных ; и иногда используются людьми для неврологического или психотропного воздействия вещества. Известные примеры триптаминовых алкалоидов включают псилоцибин (от « псилоцибиновых грибов ») и ДМТ . В Южной Америке диметилтриптамин получают из многочисленных растительных источников, таких как чакруна , и его часто используют в отварах аяуаски . Также было изготовлено много синтетических триптаминов, включая лекарство от мигрени суматриптан и психоделические препараты . Исследование 2022 года показало, что разнообразие триптаминов, присутствующих в лесных грибах, может влиять на терапевтическое воздействие. [1]

Структура триптамина, в частности его индольное кольцо, может быть частью структуры некоторых более сложных соединений, например: ЛСД , ибогаин , митрагинин и йохимбин . Тщательное исследование десятков соединений триптамина было опубликовано Энн и Александром Шульгиным под названием TiHKAL .

Список замещенных триптаминов

Избранные триптамины
Химическая структураКраткое имяИсточникЗамена кольцаР Н1Р Н2Полное имяНомер CAS
ТриптаминЖивотные, растения, грибыЧАСЧАСЧАС3-(2-аминоэтил)индол / 2-(1H-индол-3-ил)этанамин61-54-1
НМТРастенияЧАСЧАСГл 3N-methyltryptamine61-49-4
2-HO-NMTPlants2-OHHCH32-hydroxy-N-methyltryptamine106987-89-7
5-MeO-NMTPlants5-OCH3HCH35-methoxy-N-methyltryptamine2009-03-2
SerotoninAnimals, plants5-OHHH5-hydroxytryptamine50-67-9
Nω-Methylserotonin (norbufotenin)Plants5-OHHCH35-hydroxy-N-methyltryptamine1134-01-6
BufoteninAnimals, plants, fungi5-OHCH3CH35-hydroxy-N,N-dimethyltryptamine487-93-4
BufotenidineAmphibians5-O−(CH3)33-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate487-91-2
MelatoninAnimals, plants, microbes5-OCH3HO=C-CH35-methoxy-N-acetyltryptamine73-31-4
N-AcetylserotoninAnimals5-OHHO=C-CH35-hydroxy-N-acetyltryptamine1210-83-9
6-HydroxymelatoninAnimals5-OCH3, 6-OHHO=C-CH3N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide2208-41-5
4-HO-NMTFungi4-OHHCH34-hydroxy-N-methyltryptamine28363-70-4
PsilocinFungi4-OHCH3CH34-hydroxy-N,N-dimethyltryptamine520-53-6
NorbaeocystinFungi4-OPO3H2HH4-phosphoryloxy-tryptamine21420-59-7
BaeocystinFungi4-OPO3H2HCH34-phosphoryloxy-N-methyl-tryptamine21420-58-6
PsilocybinFungi4-OPO3H2CH3CH34-phosphoryloxy-N,N-dimethyltryptamine520-52-5
AeruginascinFungi4-OPO3H2(CH3)3[3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate114264-95-8
DMTAnimals, plantsHCH3CH3N,N-dimethyltryptamine61-50-7
LespedaminePlants1-OCH3CH3CH31-methoxy-N,N-dimethyltryptamine4335-93-7
5-MeO-DMTAnimals, plants5-OCH3CH3CH35-methoxy-N,N-dimethyltryptamine1019-45-0
5-Bromo-DMTMarine sponges, invertebrates5-BrCH3CH35-bromo-N,N-dimethyltryptamine17274-65-6
6-BromotryptamineMarine invertebrates6-BrHH6-bromotryptamine96624-18-9
5,6-DibromotryptamineMarine invertebrates5,6-BrHH5,6-dibromotryptamine
5,6-Dibromo-NMTMarine invertebrates5,6-BrHCH35,6-dibromo-N-methyltryptamine
5,6-Dibromo-DMTMarine sponges, invertebrates5,6-BrCH3CH35,6-dibromo-N,N-dimethyltryptamine72853-80-6
DesformylflustrabromineMarine invertebrates2-(α,α-dimethylallyl), 6-BrHCH32-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine474657-72-2
Convolutindole AMarine invertebrates2,4,6-Br, 1,7-OCH3CH3CH31,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine443356-86-3
Acetryptineartificial5-COCH3HH5-Acetyltryptamine3551-18-6
5-BTartificial5-OCH2C6H5HH5-Benzyloxytryptamine20776-45-8
5-CTartificial5-CONH2HH5-Carboxamidotryptamine74885-09-9
5-(Nonyloxy)tryptamineartificial5-O(CH2)8CH3HH5-nonyloxytryptamine157798-12-4
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-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate
Pyr-TartificialH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole14008-96-9
4-HO-pyr-Tartificial4-OH(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol63097-26-7
5-MeO-pyr-Tartificial5-OCH3(CH2)45-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole3949-14-2
IndolylethylfentanylartificialH(CH2)5-4-N(COCH2CH3)C6H5N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide58399-46-5
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-DMTartificial5-SCH3CH3CH35-methylthio-N,N-dimethyltryptamine5102-11-4
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
5-Ethoxy-DMTartificial5-OCH2CH3CH3CH35-ethoxy-N,N-dimethyltryptamine855245-09-9
5-Ethoxy-METartificial5-OCH2CH3CH3CH2CH35-ethoxy-N-methyl-N-ethyltryptamine
5-Ethoxy-DETartificial5-OCH2CH3CH2CH3CH2CH35-ethoxy-N,N-diethyltryptamine
5-Ethoxy-MPTartificial5-OCH2CH3CH3CH2CH2CH35-ethoxy-N-methyl-N-propyltryptamine
5-Ethoxy-EPTartificial5-OCH2CH3CH2CH3CH2CH2CH35-ethoxy-N-ethyl-N-propyltryptamine
5-Ethoxy-DPTartificial5-OCH2CH3CH2CH2CH3CH2CH35-ethoxy-N,N-dipropyltryptamine
5-Ethoxy-MiPTartificial5-OCH2CH3CH3CH(CH3)25-ethoxy-N-methyl-N-isopropyltryptamine
5-Ethoxy-EiPTartificial5-OCH2CH3CH2CH3CH(CH3)25-ethoxy-N-ethyl-N-isopropyltryptamine
5-Ethoxy-DiPTartificial5-OCH2CH3CH(CH3)2CH(CH3)25-ethoxy-N,N-diisopropyltryptamine
5-Ethoxy-DALTartificial5-OCH2CH3H2C=CH-CH2H2C=CH-CH25-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-CH3CH3CH35,N,N-trimethyltryptamine22120-39-4
5-Ethyl-DMTartificial5-CH2CH3CH3CH35-ethyl-N,N-dimethyltryptamine171783-25-8
5-Isopropyl-DMTartificial5-CH(CH3)2CH3CH35-isopropyl-N,N-dimethyltryptamine156281-04-8
5-(t-Butyl)-DMT [13]artificial5-C(CH3)3CH3CH35-(tert-butyl)-N,N-dimethyltryptamine
5-Fluoro-DMTartificial5-FCH3CH35-fluoro-N,N-dimethyltryptamine22120-36-1
5-Fluoro-METartificial5-FCH3CH2CH35-fluoro-N-methyl-N-ethyltryptamine
5-Fluoro-DETartificial5-FCH2CH3CH2CH35-fluoro-N,N-diethyltryptamine
5-Fluoro-EPTartificial5-FCH2CH3CH2CH2CH35-fluoro-N-ethyl-N-propyltryptamine
5-Fluoro-DPTartificial5-FCH2CH2CH3CH2CH2CH35-fluoro-N,N-dipropyltryptamine
5-Fluoro-PiPTartificial5-FCH2CH2CH3CH(CH3)25-fluoro-N-propyl-N-isopropyltryptamine
5-Fluoro-PcBTartificial5-FCH2CH2CH3CH(CH2)35-fluoro-N-propyl-N-cyclobutyltryptamine
5-Fluoro-iPcBTartificial5-FCH(CH3)2CH(CH2)35-fluoro-N-isopropyl-N-cyclobutyltryptamine
5-Fluoro-DiPTartificial5-FCH(CH3)2CH(CH3)25-fluoro-N,N-diisoproptryptamine
5-Fluoro-sBALTartificial5-FCH(CH3)CH2CH3CH2CH=CH25-fluoro-N-sec-butyl-N-allyltryptamine
5-Fluoro-M1MALTartificial5-FCH3CH(CH3)CH=CH25-fluoro-N-methyl-N-(1-methylallyl)tryptamine
5-Chloro-DMTartificial5-ClCH3CH35-chloro-N,N-dimethyltryptamine22120-32-7
5-Iodo-DMTartificial5-ICH3CH35-iodo-N,N-dimethyltryptamine22120-38-3
5-TFM-DMTartificial5-CF3CH3CH35-(trifluoromethyl)-N,N-dimethyltryptamine2418713-32-1
5-TFMO-DMT[14]artificial5-OCF3CH3CH35-(trifluoromethoxy)-N,N-dimethyltryptamine
5-Nitro-DMT[15]artificial5-NO2CH3CH35-nitro-N,N-dimethyltryptamine69937-13-9
5-CN-DMTartificial5-C≡NCH3CH35-cyano-N,N-dimethyltryptamine17380-42-6
5-CN-DPTartificial5-C≡NCH2CH2CH3CH2CH2CH35-cyano-N,N-dipropyltryptamine74885-19-1
Almotriptanartificial5-(CH2SO2N(CH2)4)CH3CH3N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine154323-57-6
Rizatriptanartificial5-(CH2(N3(CH)2))CH3CH3N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine145202-66-0
Sumatriptanartificial5-(CH2SO2NHCH3)CH3CH31-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide103628-46-2
Zolmitriptanartificial5-(CHNHC=OOCH2)CH3CH35-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine139264-17-8
6-Fluoro-DMTartificial6-FCH3CH36-fluoro-N,N-dimethyltryptamine1511-31-5
6-Fluoro-DET[16]artificial6-FCH2CH3CH2CH36-fluoro-N,N-diethyltryptamine2836-69-3
6-Chloro-DMTartificial6-ClCH3CH36-chloro-N,N-dimethyltryptamine25390-72-1
6-Methyl-DMTartificial6-CH3CH3CH36,N,N-trimethyltryptamine
6-Hydroxy-DMTartificial6-OHCH3CH36-hydroxy-N,N-dimethyltryptamine1476-33-1
6-Hydroxy-DETartificial6-OHCH3CH36-hydroxy-N,N-diethyltryptamine1476-59-1
6-Methoxy-DMTartificial6-OCH3CH3CH36-methoxy-N,N-dimethyltryptamine2426-88-2
7-Methyl-DMTartificial7-CH3CH3CH37,N,N-trimethyltryptamine65882-39-5
7-Ethyl-DMTartificial7-CH2CH3CH3CH37-ethyl-N,N-dimethyltryptamine
7-Chloro-DMTartificial7-ClCH3CH37-chloro-N,N-dimethyltryptamine
7-Bromo-DMT[17]artificial7-BrCH3CH37-bromo-N,N-dimethyltryptamine74798-68-8
7-Methoxy-DMTartificial7-OCH3CH3CH37-methoxy-N,N-dimethyltryptamine
7-Methoxy-MiPTartificial7-OCH3CH3CH(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
NBoc-DMTartificial1-OCOC(CH3)3CH3CH31-(t-butoxycarbonyl)-N,N-dimethyltryptamine
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-Fluoropsilocinartificial4-OH,6-FCH3CH34-hydroxy-6-fluoro-N,N-dimethyltryptamine312314-12-8
6-Fluoro-5-MeO-DMTartificial5-OCH3,6-FCH3CH35-methoxy-6-fluoro-N,N-dimethyltryptamine
5,6-Difluoro-EPTartificial5-F, 6-FCH2CH3CH2CH2CH35,6-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-OCH3CH3CH35-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-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine82173-82-8
5,6-FUR-DMT (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-(2H,5H-[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-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine
Chemical StructureShort NameOriginRing SubstitutionRN1RN2Full NameCAS Number

List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen.[19][20][21] α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.[21] This is analogous to α-methylation of phenethylamine into amphetamine.[21]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[22][23][24][25] and produce psychostimulant, entactogen, and/or psychedelic effects.[19][20][21] The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[20][21] In accordance with its action as a dual releasing agent of serotonin and dopamine, αET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as αMT, 5-MeO-αMT, and various others.[26]

StructureCommon nameChemical nameCAS number
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-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}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-1H-indol-3-yl)propan-2-yl](methyl)amine4822-13-3
Indolylpropylaminopentane (α,N-DPT)1-(1H-indol-3-yl)-N-propylpentan-2-amine
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-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-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-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole143322-58-1
Z5247692566[4][30]4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine
BK-NM-AMT (α,N-dimethyl-β-ketotryptamine)[31][32][33]1-(1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine)[34][35][36][33]1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[36][37][38]1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one
BK-5Br-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[36][39][40]1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one

List of substituted β-ketotryptamines

A number of β-ketotryptamines (beta-ketotryptamines) are known.[31][33][36] These compounds are α-alkyl-β-ketotryptamines and are analogous to the cathinones (β-ketoamphetamines) of the related phenethylamine family. Known β-ketotryptamines include BK-NM-AMT, BK-5F-NM-AMT, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT.[31][33][36] They act as monoamine releasing agents.[31][33][36]

A number of related compounds are known, with a similar structure but having the indole core flipped (isotryptamines) and/or replaced with related cores such as indene, indoline, indazole, indolizine, benzothiophene, or benzofuran. Like tryptamines, these related compounds 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
C-DMT [41]2-(3H-inden-1-yl)-N,N-dimethylethanamine
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
3-APBT1-(1-benzothiophen-3-yl)propan-2-amine1201-27-0
Mebfap3-(2-aminopropyl)-5-methoxybenzofuran140853-59-4
Isotryptamine2-indol-1-ylethanamine13708-58-2
isoAMT1-indol-1-ylpropan-2-amine1227465-67-9
(S)-5,6-Difluoro-isoAMT [42](S)-1-(5,6-difluoroindol-1-yl)propan-2-amine
Ro60-0175(S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine169675-09-6
isoDMT2-indol-1-yl-N,N-dimethylethanamine87482-09-5
5-MeO-isoDMT2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine
6-MeO-isoDMT2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine
AAZ-A-154 (DLX-001)(2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine2227169-50-4
2ZEDMA2-indolizin-1-yl-N,N-dimethylethanamine
1ZP2MA1-indolizin-1-yl-N-methylpropan-2-amine
1Z2MAP1O1-indolizin-3-yl-2-(methylamino)propan-1-one2110204-31-2
Example 16 [43][44]1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
Example 1 [45]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 [46](S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine478132-12-6
Example 3 [47](S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine890087-75-9
Example 1 [48](S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine1373917-69-1
YM-348(2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine372163-84-3
2-desethyl-YM-348 [49](2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine748116-94-1
I-32 [50]3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
2-Azapsilocin (Psilocin indazole analogue, P-6)[51]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[52]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

Tryptamine-based therapeutics

DrugMechanismTreatmentEffectStructure
Sumatriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Sumatriptan
Rizatriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Rizatriptan
Zolmitriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Zolmitriptan
Almotriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Almotriptan
Eletriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Eletriptan
Frovatriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Frovatriptan
Naratriptan[53]5-HT1B and 5-HT1D agonistMigraine HeadachesVasoconstriction of brain blood vessels
Naratriptan

Further reading

See also

References

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