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substituted tryptamine

{{Short description|Class of indoles}}

Image:Tryptamine rests General Formula V.svg

Image:Tryptamine structure.svg

Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine 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.{{Cite web |last1=Chemistry |first1=University of |last2=Prague |first2=Technology |title=Concentrations of psychoactive compounds in mushrooms found to be extremely variable |url=https://phys.org/news/2022-12-psychoactive-compounds-mushrooms-extremely-variable.html |access-date=2022-12-26 |website=phys.org |language=en}}

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

{{Incomplete list|date=October 2021}}

{{Sticky}}

class="wikitable sortable sticky-header" style="font-size: small;"
+ Selected tryptamines
Structure

! Name

! Origin

! Ring sub.

! RN1

! RN2

! width="50px" | Chemical name

! CAS #

130pxTryptamineAnimals, plants, fungiHHH3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine61-54-1
120pxNMTPlantsHHCH3N-methyltryptamine61-49-4
120px2-HO-NMTPlants2-OHHCH32-hydroxy-N-methyltryptamine106987-89-7
120px5-MeO-NMTPlants5-OCH3HCH35-methoxy-N-methyltryptamine2009-03-2
120pxSerotonin (5-HT)Animals, plants5-OHHH5-hydroxytryptamine50-67-9
120pxNω-Methylserotonin (norbufotenin)Plants5-OHHCH35-hydroxy-N-methyltryptamine1134-01-6
120pxBufotenin (5-HO-DMT)Animals, plants, fungi5-OHCH3CH35-hydroxy-N,N-dimethyltryptamine487-93-4
120pxBufotenidineAmphibians5-O−colspan=2|(CH3)33-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate487-91-2
120pxBufoviridineAmphibians5-SOCH3CH35-sulfooxy-N,N-dimethyltryptamine16369-08-7
120pxMelatoninAnimals, plants, microbes5-OCH3HO=C-CH35-methoxy-N-acetyltryptamine73-31-4
120pxN-AcetylserotoninAnimals5-OHHO=C-CH35-hydroxy-N-acetyltryptamine1210-83-9
120px6-HydroxymelatoninAnimals5-OCH3, 6-OHHO=C-CH3N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide2208-41-5
120px4-HydroxytryptamineFungi4-OHHH4-hydroxytryptamine570-14-9
120px4-HO-NMTFungi4-OHHCH34-hydroxy-N-methyltryptamine28363-70-4
120pxPsilocin (4-HO-DMT)Fungi4-OHCH3CH34-hydroxy-N,N-dimethyltryptamine520-53-6
120px4-HO-TMTFungi4-OHCH3CH34-hydroxy-N,N,N-trimethyltryptammonium262285-41-6
120pxNorbaeocystinFungi4-OPO3H2HH4-phosphoryloxy-tryptamine21420-59-7
120pxBaeocystinFungi4-OPO3H2HCH34-phosphoryloxy-N-methyl-tryptamine21420-58-6
120pxPsilocybinFungi4-OPO3H2CH3CH34-phosphoryloxy-N,N-dimethyltryptamine520-52-5
120pxAeruginascinFungi4-OPO3H2colspan=2|(CH3)3[3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate114264-95-8
120pxDMTAnimals, plantsHCH3CH3N,N-dimethyltryptamine61-50-7
120pxLespedaminePlants1-OCH3CH3CH31-methoxy-N,N-dimethyltryptamine4335-93-7
120px5-MeO-DMTAnimals, plants5-OCH3CH3CH35-methoxy-N,N-dimethyltryptamine1019-45-0
120px5-Bromo-DMTMarine sponges, invertebrates5-BrCH3CH35-bromo-N,N-dimethyltryptamine17274-65-6
120px6-BromotryptamineMarine invertebrates6-BrHH6-bromotryptamine96624-18-9
120px5,6-DibromotryptamineMarine invertebrates5,6-BrHH5,6-dibromotryptamine
120px5,6-Dibromo-NMTMarine invertebrates5,6-BrHCH35,6-dibromo-N-methyltryptamine
120px5,6-Dibromo-DMTMarine sponges, invertebrates5,6-BrCH3CH35,6-dibromo-N,N-dimethyltryptamine72853-80-6
120pxDesformylflustrabromineMarine invertebrates2-(α,α-dimethylallyl), 6-BrHCH32-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine474657-72-2
120pxConvolutindole AMarine invertebrates2,4,6-Br, 1,7-OCH3CH3CH31,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine443356-86-3
120pxAcetryptine

|artificial

| 5-COCH3

| H

| H

| 5-Acetyltryptamine

| 3551-18-6

130px5-BT

|artificial

| 5-OCH2C6H5

| H

| H

| 5-Benzyloxytryptamine

| 20776-45-8

120px5-CT

|artificial

| 5-CONH2

| H

| H

| 5-Carboxamidotryptamine

| 74885-09-9

130px5-(Nonyloxy)tryptamineartificial5-O(CH2)8CH3HH5-nonyloxytryptamine157798-12-4
120px2-Methyl-5-hydroxytryptamine

|artificial

| 2-CH3, 5-OH

| H

| H

| 3-(2-aminoethyl)-2-methyl-1H-indol-5-ol

| 78263-90-8

120pxNET

|artificial

| H

| H

| CH2CH3

| N-ethyltryptamine

| 61-53-0

120pxNiPT

|artificial

| H

| H

| CH(CH3)2

| N-isopropyltryptamine

| 14121-10-9

120pxNcPT

|artificial

| H

| H

| C3H5

| N-cyclopropyltryptamine

|

120pxNSBT

|artificial

| H

| H

| CH(CH3)CH2CH3

| N-sec-butyltryptamine

|

120pxNTBT

|artificial

| H

| H

| C(CH3)3

| N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine

|

130px5-MeO-T-NBOMe

|artificial

| 5-OCH3

| H

| CH2C6H4(o-OCH3)

| 5-methoxy-N-(ortho-methoxybenzyl)tryptamine

| 1335331-37-7

130px5-MT-NB3OMe {{cite journal | vauthors = Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK | title = 5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines | journal = PLOS ONE | volume = 14 | issue = 1 | pages = e0209804 | date = 2019 | pmid = 30629611 | pmc = 6328172 | doi = 10.1371/journal.pone.0209804 | bibcode = 2019PLoSO..1409804T | doi-access = free }}

|artificial

| 5-OCH3

| H

| CH2C6H4(m-OCH3)

| 5-methoxy-N-(meta-methoxybenzyl)tryptamine

| 1648553-42-7

130px5-MeO-NBpBrT

|artificial

| 5-OCH3

| H

| CH2C6H4(p-Br)

| N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine

| 155639-13-7

130px5-MeO-34MPEMT 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

|artificial

| 5-OCH3

| CH3

| CH2CH2C6H3(p,m-OCH3)

| N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine

|

130pxIdalopirdine

|artificial

| 6-F

| H

| CH2C6H4(m-OCH2CF2CF2H)

| 2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine

| 467459-31-0

130pxZ2876442907{{cite journal | vauthors = Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, Barros-Álvarez X, Sakamoto K, Kim Y, DiBerto J, Kim K, Tummino TA, Huang S, Irwin JJ, Tarkhanova OO, Moroz Y, Skiniotis G, Kruse AC, Shoichet BK, Roth BL | display-authors = 6 | title = AlphaFold2 structures template ligand discovery | journal = bioRxiv | volume = | issue = | date = December 2023 | pmid = 38187536 | pmc = 10769324 | doi = 10.1101/2023.12.20.572662 }}

|artificial

| 4-CH3

| H

| CH2(C3HNS)-COOCH2CH3

| ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate

|

120pxPyr-TartificialHcolspan=2|(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole14008-96-9
120px4-HO-pyr-Tartificial4-OHcolspan=2|(CH2)43-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol63097-26-7
120px5-MeO-pyr-Tartificial5-OCH3colspan=2|(CH2)45-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole3949-14-2
120px4-F-5-MeO-pyr-Tartificial4-F-5-OCH3colspan=2|(CH2)44-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole344790-93-8
120pxIndolylethylfentanylartificialHcolspan=2|(CH2)5-4-N(COCH2CH3)C6H5N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide58399-46-5
120pxMET

|artificial

| H

| CH3

| CH2CH3

| N-Methyl-N-ethyltryptamine

| 5599-69-9

120pxMPT

|artificial

| H

| CH3

| CH2CH2CH3

| N-Methyl-N-propyltryptamine

| 850032-72-3

120pxMiPT

|artificial

| H

| CH3

| CH(CH3)2

| N-Methyl-N-isopropyltryptamine

| 96096-52-5

120pxMcPT

|artificial

| H

| CH3

| C3H5

| N-Methyl-N-cyclopropyltryptamine

| 1373918-63-8

120pxEcPT

|artificial

| H

| CH2CH3

| C3H5

| N-ethyl-N-cyclopropyltryptamine

|

120pxPcPT

|artificial

| H

| CH2CH2CH3

| C3H5

| N-propyl-N-cyclopropyltryptamine

|

120pxiPcPT

|artificial

| H

| CH(CH3)2

| C3H5

| N-isopropyl-N-cyclopropyltryptamine

|

120pxDcPT

|artificial

| H

| C3H5

| C3H5

| N,N-dicyclopropyltryptamine

| 1373918-62-7

120pxMBT

|artificial

| H

| CH3

| (CH2)3CH3

| N-Methyl-N-butyltryptamine

| 848130-12-1

120pxMSBT

|artificial

| H

| CH3

| CH(CH3)CH2CH3

| N-Methyl-N-sec-butyltryptamine

|

120pxMiBT

|artificial

| H

| CH3

| CH2CH(CH3)2

| N-Methyl-N-iso-butyltryptamine

|

120pxMcPMT

|artificial

| H

| CH3

| CH2C3H5

| N-Methyl-N-(cyclopropylmethyl)tryptamine

|

120pxDET

|artificial

| H

| CH2CH3

| CH2CH3

| N,N-diethyltryptamine

| 61-51-8

120pxEPT

|artificial

| H

| CH2CH3

| CH2CH2CH3

| N-Ethyl-N-propyltryptamine

| 850032-68-7

120pxEiPT

|artificial

| H

| CH2CH3

| CH(CH3)2

| N-Ethyl-N-isopropyltryptamine

| 848130-11-0

120pxDPT

|artificial

| H

| CH2CH2CH3

| CH2CH2CH3

| N,N-dipropyltryptamine

| 61-52-9

120pxPiPT

|artificial

| H

| CH2CH2CH3

| CH(CH3)2

| N-Propyl-N-isopropyltryptamine

| 1354632-00-0

120pxDiPT

|artificial

| H

| CH(CH3)2

| CH(CH3)2

| N,N-diisopropyltryptamine

| 14780-24-6

120pxEBT

|artificial

| H

| CH2CH3

| (CH2)3CH3

| N-ethyl-N-butyltryptamine

|

120pxPBT

|artificial

| H

| CH2CH2CH3

| (CH2)3CH3

| N-propyl-N-butyltryptamine

|

120pxiPsBT

|artificial

| H

| CH(CH3)2

| CH(CH3)CH2CH3

| N-isopropyl-N-sec-butyltryptamine

|

120pxDBT

|artificial

| H

| (CH2)3CH3

| (CH2)3CH3

| N,N-dibutyltryptamine

| 15741-77-2

120pxDIBT

|artificial

| H

| CH2CH(CH3)2

| CH2CH(CH3)2

| N,N-diisobutyltryptamine

| 63938-64-7

120pxDSBT

|artificial

| H

| CH(CH3)CH2CH3

| CH(CH3)CH2CH3

| N,N-disecbutyltryptamine

|

120pxMALT

|artificial

| H

| CH3

| H2C=CH-CH2

| N-methyl-N-allyltryptamine

| 1366416-29-6

120pxDALT

|artificial

| H

| H2C=CH-CH2

| H2C=CH-CH2

| N,N-diallyltryptamine

| 60676-77-9

120pxALiPT

|artificial

| H

| H2C=CH-CH2

| CH(CH3)2

| N-allyl-N-isopropyltryptamine

|

120px2-Methyl-DMT

|artificial

| 2-CH3

| CH3

| CH3

| (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine

| 1080-95-1

120px2-Me-DET

|artificial

| 2-CH3

| CH2CH3

| CH2CH3

| N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine

| 26628-88-6

120px4-Amino-DMT {{cite journal | vauthors = McKay JB, Parkhurst RM, Silverstein RM, Skinner WA | title = Analogues of Psilocin and Lysergic acid diethylamide I. Chloro, Nitro, and Amino Derivatives of 3-Substituted Indoles. | journal = Canadian Journal of Chemistry | date = October 1963 | volume = 41 | issue = 10 | pages = 2585–2590 | doi = 10.1139/v63-378}}

|artificial

| 4-NH2

| CH3

| CH3

| 4-amino-N,N-dimethyltryptamine

| 60331-61-5

120px4-Methyl-DMT

|artificial

| 4-CH3

| CH3

| CH3

| 4,N,N-trimethyltryptamine

| 28289-23-8

120px4-MeO-DMT

|artificial

| 4-OCH3

| CH3

| CH3

| 4-methoxy-N,N-dimethyltryptamine

| 3965-97-7

120px4-MeO-MiPT

|artificial

| 4-OCH3

| CH3

| CH(CH3)2

| 4-methoxy-N-methyl-N-isopropyltryptamine

| 96096-53-6

120px4-MeO-DiPT

|artificial

| 4-OCH3

| CH(CH3)2

| CH(CH3)2

| 4-methoxy-N,N-diisopropyltryptamine

|

120px4-AcO-DMT

|artificial

| 4-OCOCH3

| CH3

| CH3

| 4-acetoxy-N,N-dimethyltryptamine

| 92292-84-7

120px4-PrO-DMT

|artificial

| 4-OCOCH2CH3

| CH3

| CH3

| 4-propionyloxy-N,N-dimethyltryptamine

| 1373882-11-1

120pxRE-109 (4-GO-DMT)

|artificial

| 4-OCO(CH2)3COOH

| CH3

| CH3

| 4-glutaryloxy-N,N-dimethyltryptamine

|

120px4-HO-MET

|artificial

| 4-OH

| CH3

| CH2CH3

| 4-hydroxy-N-methyl-N-ethyltryptamine

| 77872-41-4

120px4-Acetoxy-MET

|artificial

| 4-OCOCH3

| CH3

| CH2CH3

| 4-acetoxy-N-methyl-N-ethyltryptamine

| 1445751-40-5

120px4-PO-MET

|artificial

| 4-OPO3H2

| CH3

| CH2CH3

| 4-phosphoryloxy-N-methyl-N-ethyltryptamine

|

120px4-HO-DET

|artificial

| 4-OH

| CH2CH3

| CH2CH3

| 4-hydroxy-N,N-diethyltryptamine

| 22204-89-3

120px4-Acetoxy-DET

|artificial

| 4-OCOCH3

| CH2CH3

| CH2CH3

| 4-acetoxy-N,N-diethyltryptamine

| 1135424-15-5

120px4-PO-DET

|artificial

| 4-OPO3H2

| CH2CH3

| CH2CH3

| 4-phosphoryloxy-N,N-diethyltryptamine

| 60480-02-6

120px4-HO-EPT

|artificial

| 4-OH

| CH2CH3

| CH2CH2CH3

| 4-hydroxy-N-ethyl-N-propyltryptamine

| 2595431-59-5

120px4-PO-EPT

|artificial

| 4-OPO3H2

| CH2CH3

| CH2CH2CH3

| 4-phosphoryloxy-N-ethyl-N-propyltryptamine

|

120px4-AcO-EiPT

|artificial

| 4-OCOCH3

| CH2CH3

| CH(CH3)2

| 4-acetoxy-N-ethyl-N-isopropyltryptamine

|

120px4-HO-MPT

|artificial

| 4-OH

| CH3

| CH2CH2CH3

| 4-hydroxy-N-methyl-N-propyltryptamine

| 763035-03-6

120px4-HO-MiPT

|artificial

| 4-OH

| CH(CH3)2

| CH3

| 4-hydroxy-N-isopropyl-N-methyltryptamine

| 77872-43-6

120px4-Acetoxy-MiPT

|artificial

| 4-OCOCH3

| CH3

| CH(CH3)2

| 4-acetoxy-N-methyl-N-isopropyltryptamine

| 1024612-25-6

120px4-HO-MALT{{cite journal | vauthors = Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL | title = Investigation of the Structure-Activity Relationships of Psilocybin Analogues | journal = ACS Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 533–542 | date = April 2021 | pmid = 33860183 | pmc = 8033608 | doi = 10.1021/acsptsci.0c00176 }}

|artificial

| 4-OH

| CH3

| H2C=CH-CH2

| 4-hydroxy-N-Methyl-N-allyltryptamine

|

120px4-AcO-MALT{{cite journal | vauthors = Pham DN, Chadeayne AR, Golen JA, Manke DR | title = Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug | journal = Acta Crystallographica Section E | volume = 77 | issue = Pt 2 | pages = 101–106 | date = February 2021 | pmid = 33614134 | pmc = 7869532 | doi = 10.1107/S2056989021000116 | bibcode = 2021AcCrE..77..101P }}

|artificial

| 4-OCOCH3

| CH3

| H2C=CH-CH2

| 4-acetoxy-N-Methyl-N-allyltryptamine

|

120px4-HO-NALTSherwood AM, Burkhartzmeyer EK, Williamson SE, Baumann MH, Glatfelter GC. Psychedelic-like Activity of Norpsilocin Analogues. ACS Chem Neurosci. 2024 Jan 17;15(2):315-327. {{doi|10.1021/acschemneuro.3c00610}} {{PMID|38189238}}

|artificial

| 4-OH

| H

| H2C=CH-CH2

| 4-hydroxy-N-allyltryptamine

|

120px4-HO-MSBT

|artificial

| 4-OH

| CH(CH3)CH2CH3

| CH3

| 4-hydroxy-N-sec-butyl-N-methyltryptamine

|

120px4-HO-EiBT

|artificial{{cite patent | url = https://patents.google.com/patent/WO2023115167A1/en?oq=WO2023115167 | country = WO | number = 2023115167| inventor = Banister S, Jorgensen W, Jinlong T | title = Compounds | assignee = Psylo Pty Ltd. | pubdate = 29 June 2023 }}

| 4-OH

| CH2CH(CH3)2

| CH2CH3

| 4-hydroxy-N-iso-butyl-N-ethyltryptamine

|

120px4-HO-McPT

|artificial

| 4-OH

| C3H5

| CH3

| 4-hydroxy-N-cyclopropyl-N-methyltryptamine

| 2883663-05-4

120px4-HO-McPeT

|artificial

| 4-OH

| C5H9

| CH3

| 4-hydroxy-N-cyclopentyl-N-methyltryptamine

| 77872-48-1

120px4-HO-McPMT {{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021179091&_cid=P20-KY4AHZ-40696-1 | inventor = Kozikowski A, Shaprio G, Tueckmantel W, McCorvy J | title = 3-(2-(Aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-HT2 receptor modulators | country = WO | number = 2021179091 | assign1 = Bright Minds Biosciences Inc. | assign2 = The Medical College Of Wisconsin Inc. | pubdate = 16 September 2021 }}

|artificial

| 4-OH

| CH2C3H5

| CH3

| 4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine

|

120px4-HO-DPT

|artificial

| 4-OH

| CH2CH2CH3

| CH2CH2CH3

| 4-hydroxy-N,N-dipropyltryptamine

| 63065-88-3

120px4-AcO-DPT

|artificial

| 4-OCOCH3

| CH2CH2CH3

| CH2CH2CH3

| 4-acetoxy-N,N-dipropyltryptamine

| 1445751-75-6

120px4-HO-PiPT

|artificial

| 4-OH

| CH2CH2CH3

| CH(CH3)2

| 4-hydroxy-N-propyl-N-isopropyltryptamine

|

120px4-AcO-PiPT

|artificial

| 4-OCOCH3

| CH2CH2CH3

| CH(CH3)2

| 4-acetoxy-N-propyl-N-isopropyltryptamine

|

120px4-HO-DIPT

|artificial

| 4-OH

| CH(CH3)2

| CH(CH3)2

| 4-hydroxy-N,N-diisopropyltryptamine

| 132328-45-1

120px4-Acetoxy-DiPT

|artificial

| 4-OCOCH3

| CH(CH3)2

| CH(CH3)2

| 4-acetoxy-N,N-diisopropyltryptamine

| 936015-60-0

120px4-PrO-DiPT

|artificial

| 4-OCOCH2CH3

| CH(CH3)2

| CH(CH3)2

| 4-propionyloxy-N,N-diisopropyltryptamine

| 1373882-13-3

120pxRE-104 (FT-104; 4-GO-DiPT)

|artificial

| 4-OCO(CH2)3COOH

| CH(CH3)2

| CH(CH3)2

| 4-glutaryloxy-N,N-diisopropyltryptamine

|

120px4-PO-DiPT

|artificial

| 4-OPO3H2

| CH(CH3)2

| CH(CH3)2

| 4-phosphoryloxy-N,N-diisopropyltryptamine

| 1373882-09-7

120px4-HO-DALT

|artificial

| 4-OH

| H2C=CH-CH2

| H2C=CH-CH2

| 4-hydroxy-N,N-diallyltryptamine

| 2173386-70-2

120px4-AcO-DALT

|artificial

| 4-OCOCH3

| H2C=CH-CH2

| H2C=CH-CH2

| 4-acetoxy-N,N-diallyltryptamine

| 1445751-71-2

120px4-HO-DBT

|artificial

| 4-OH

| (CH2)3CH3

| (CH2)3CH3

| 4-hydroxy-N,N-dibutyltryptamine

| 63065-89-4

120px4-HO-DIBT

|artificial

| 4-OH

| CH2CH(CH3)2

| CH2CH(CH3)2

| 4-hydroxy-N,N-diisobutyltryptamine

|

120px4-HO-DSBT

|artificial

| 4-OH

| CH(CH3)CH2CH3

| CH(CH3)CH2CH3

| 4-hydroxy-N,N-disecbutyltryptamine

| 127507-01-1

120px5-MeO-MET

|artificial

| 5-OCH3

| CH2CH3

| CH3

| 5-methoxy-N-Methyl-N-ethyltryptamine

| 16977-53-0

120px5-MeO-DET

|artificial

| 5-OCH3

| CH2CH3

| CH2CH3

| 5-methoxy-N,N-diethyltryptamine

| 2454-70-8

120px5-MeO-MPT

|artificial

| 5-OCH3

| CH3

| CH2CH2CH3

| 5-methoxy-N-methyl-N-propyltryptamine

|

120px5-MeO-EPT

|artificial

| 5-OCH3

| CH2CH3

| CH2CH2CH3

| 5-methoxy-N-ethyl-N-propyltryptamine

| 850032-67-6

120px5-MeO-DPT

|artificial

| 5-OCH3

| CH2CH2CH3

| CH2CH2CH3

| 5-methoxy-N,N-dipropyltryptamine

| 69496-75-9

120px5-MeO-MALT

|artificial

| 5-OCH3

| H2C=CH-CH2

| CH3

| 5-methoxy-N-Methyl-N-allyltryptamine

| 1373918-64-9

120px5-MeO-DALT

|artificial

| 5-OCH3

| H2C=CH-CH2

| H2C=CH-CH2

| 5-methoxy-N,N-diallyltryptamine

| 928822-98-4

120px5-MeO-ALiPT

|artificial

| 5-OCH3

| H2C=CH-CH2

| CH2CH(CH3)2

| 5-methoxy-N-allyl-N-isopropyltryptamine

|

120px5-MeO-MiPT

|artificial

| 5-OCH3

| CH3

| CH(CH3)2

| 5-methoxy-N,N-methylisopropyltryptamine

| 96096-55-8

120px5,6-MeO-MiPT

|artificial

| 5-OCH3, 6-OCH3

| CH3

| CH(CH3)2

| 5,6-dimethoxy-N,N-methylisopropyltryptamine

|

120px5-MeO-McPT

|artificial

| 5-OCH3

| CH3

| C3H5

| 5-methoxy-N-methyl-N-cyclopropyltryptamine

|

120px5-MeO-McBT

|artificial

| 5-OCH3

| CH3

| C4H7

| 5-methoxy-N-methyl-N-cyclobutyltryptamine

|

120px5-MeO-EiPT

|artificial

| 5-OCH3

| CH2CH3

| CH(CH3)2

| 5-methoxy-N-ethyl-N-isopropyltryptamine

| 850032-66-5

120px5-MeO-PiPT

|artificial

| 5-OCH3

| CH2CH2CH3

| CH(CH3)2

| 5-methoxy-N-propyl-N-isopropyltryptamine

|

120px5-MeO-DIPT

|artificial

| 5-OCH3

| CH(CH3)2

| CH(CH3)2

| 5-methoxy-N,N-diisopropyltryptamine

| 4021-34-5

120px5-MeO-DBT

|artificial

| 5-OCH3

| (CH2)3CH3

| (CH2)3CH3

| 5-methoxy-N,N-dibutyltryptamine

| 73785-42-9

120px5-MeO-DSBT

|artificial

| 5-OCH3

| CH(CH3)CH2CH3

| CH(CH3)CH2CH3

| 5-methoxy-N,N-di-sec-butyltryptamine

|

120px5-MeS-DMT

| artificial

| 5-SCH3

| CH3

| CH3

| 5-methylthio-N,N-dimethyltryptamine

| 5102-11-4

120px5-AcO-DMT

|artificial

| 5-OCOCH3

| CH3

| CH3

| 5-acetoxy-N,N-dimethyltryptamine

| 16977-50-7

120px5-AcO-MET {{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021101926 | inventor = Stamets PE | title = Tryptamine Compositions for Enhancing Neurite Outgrowth. | country = WO | number = 2021101926 | pubdate = 2021-05-27 | assign1 = Stamets Paul Edward | postscript = . }}

|artificial

| 5-OCOCH3

| CH3

| CH2CH3

| 5-acetoxy-N-methyl-N-ethyltryptamine

|

120px5-AcO-DET

|artificial

| 5-OCOCH3

| CH2CH3

| CH2CH3

| 5-acetoxy-N,N-diethyltryptamine

|

120px5-AcO-EPT {{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021168082 | inventor = Kruegel AC, Sporn J | title = Specific Tryptamines for use in the Treatment of Mood Disorders. | country = WO | number = 2021168082 | pubdate = 26 August 2021 }}

|artificial

| 5-OCOCH3

| CH2CH3

| CH2CH2CH3

| 5-acetoxy-N-ethyl-N-propyltryptamine

|

120px5-AcO-DPT

|artificial

| 5-OCOCH3

| CH2CH2CH3

| CH2CH2CH3

| 5-acetoxy-N,N-dipropyltryptamine

|

120px5-AcO-MiPT

|artificial

| 5-OCOCH3

| CH3

| CH(CH3)2

| 5-acetoxy-N-methyl-N-isopropyltryptamine

|

120px5-AcO-DiPT

|artificial

| 5-OCOCH3

| CH(CH3)2

| CH(CH3)2

| 5-acetoxy-N,N-diisopropyltryptamine

|

120px5-Ethoxy-DMTartificial5-OCH2CH3CH3CH35-ethoxy-N,N-dimethyltryptamine855245-09-9
120px5-Ethoxy-METartificial5-OCH2CH3CH3CH2CH35-ethoxy-N-methyl-N-ethyltryptamine
120px5-Ethoxy-DETartificial5-OCH2CH3CH2CH3CH2CH35-ethoxy-N,N-diethyltryptamine
120px5-Ethoxy-MPTartificial5-OCH2CH3CH3CH2CH2CH35-ethoxy-N-methyl-N-propyltryptamine
120px5-Ethoxy-EPTartificial5-OCH2CH3CH2CH3CH2CH2CH35-ethoxy-N-ethyl-N-propyltryptamine
120px5-Ethoxy-DPTartificial5-OCH2CH3CH2CH2CH3CH2CH35-ethoxy-N,N-dipropyltryptamine
120px5-Ethoxy-MiPTartificial5-OCH2CH3CH3CH(CH3)25-ethoxy-N-methyl-N-isopropyltryptamine
120px5-Ethoxy-EiPTartificial5-OCH2CH3CH2CH3CH(CH3)25-ethoxy-N-ethyl-N-isopropyltryptamine
120px5-Ethoxy-DiPTartificial5-OCH2CH3CH(CH3)2CH(CH3)25-ethoxy-N,N-diisopropyltryptamine
120px5-Ethoxy-DALTartificial5-OCH2CH3H2C=CH-CH2H2C=CH-CH25-ethoxy-N,N-diallyltryptamine
120px5-BnO-DMT

|artificial

| 5-OCH2C6H5

| CH3

| CH3

| 5-benzyloxy-N,N-dimethyltryptamine

| 101832-88-6

120px5-HO-DET

|artificial

| 5-OH

| CH2CH3

| CH2CH3

| 5-hydroxy-N,N-diethyltryptamine

| 14009-42-8

120px5-HO-DPT

|artificial

| 5-OH

| CH2CH2CH3

| CH2CH2CH3

| 5-hydroxy-N,N-dipropyltryptamine

| 36288-75-2

120px5-HO-MiPT

|artificial

| 5-OH

| CH3

| CH(CH3)2

| 5-hydroxy-N-methyl-N-isopropyltryptamine

|

120px5-HO-DiPT

|artificial

| 5-OH

| CH(CH3)2

| CH(CH3)2

| 5-hydroxy-N,N-diisopropyltryptamine

| 36288-76-3

120px5-Methyl-DMT (5,N,N-TMT)artificial5-CH3CH3CH35,N,N-trimethyltryptamine22120-39-4
120px5-Ethyl-DMTartificial5-CH2CH3CH3CH35-ethyl-N,N-dimethyltryptamine171783-25-8
120px5-Isopropyl-DMTartificial5-CH(CH3)2CH3CH35-isopropyl-N,N-dimethyltryptamine156281-04-8
120px5-(t-Butyl)-DMT {{cite journal | vauthors = Xu YC, Schaus JM, Walker C, Krushinski J, Adham N, Zgombick JM, Liang SX, Kohlman DT, Audia JE | title = N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist | journal = Journal of Medicinal Chemistry | volume = 42 | issue = 3 | pages = 526–31 | date = February 1999 | pmid = 9986723 | doi = 10.1021/jm9805945 }}artificial5-C(CH3)3CH3CH35-(tert-butyl)-N,N-dimethyltryptamine
120px5-Fluoro-DMTartificial5-FCH3CH35-fluoro-N,N-dimethyltryptamine22120-36-1
120px5-Fluoro-METartificial5-FCH3CH2CH35-fluoro-N-methyl-N-ethyltryptamine2698331-35-8
120px5-Fluoro-DETartificial5-FCH2CH3CH2CH35-fluoro-N,N-diethyltryptamine
120px5-Fluoro-EPTartificial5-FCH2CH3CH2CH2CH35-fluoro-N-ethyl-N-propyltryptamine
120px5-Fluoro-DPTartificial5-FCH2CH2CH3CH2CH2CH35-fluoro-N,N-dipropyltryptamine
120px5-Fluoro-PiPTartificial5-FCH2CH2CH3CH(CH3)25-fluoro-N-propyl-N-isopropyltryptamine
120px5-Fluoro-PcBTartificial5-FCH2CH2CH3CH(CH2)35-fluoro-N-propyl-N-cyclobutyltryptamine
120px5-Fluoro-iPcBTartificial5-FCH(CH3)2CH(CH2)35-fluoro-N-isopropyl-N-cyclobutyltryptamine
120px5-Fluoro-DiPTartificial5-FCH(CH3)2CH(CH3)25-fluoro-N,N-diisoproptryptamine
120px5-Fluoro-sBALTartificial5-FCH(CH3)CH2CH3CH2CH=CH25-fluoro-N-sec-butyl-N-allyltryptamine
120px5-Fluoro-M1MALTartificial5-FCH3CH(CH3)CH=CH25-fluoro-N-methyl-N-(1-methylallyl)tryptamine
120px5-Chloro-DMTartificial5-ClCH3CH35-chloro-N,N-dimethyltryptamine22120-32-7
120px5-Iodo-DMTartificial5-ICH3CH35-iodo-N,N-dimethyltryptamine22120-38-3
120px5-TFM-DMTartificial5-CF3CH3CH35-(trifluoromethyl)-N,N-dimethyltryptamine2418713-32-1
120px5-TFMO-DMT{{cite patent | url = https://patentscope.wipo.int/search/docs2/pct/WO2022235927/pdf/sajUgB9feBBH7-__3mqstxlXe0bNbux38L0F3CIfqfeIoRd6DwsRFOeky38MB7P6suwn-LGhylfnZxzms7NnjL5ECezVuxHaYjY-fF3rgUuqobt_3VLz-s7oacujHa1w?docId=id00000069456988&filename=WO2022235927-PAMPH-20221110-6988.pdf | inventor = Kruegel AC | title = Novel Tryptamines and Methods of Treating Mood Disorders | country = WO | number = 2022235927 | assign1 = Gilgamesh Pharmaceuticals, Inc. | pubdate = 10 November 2022 }}artificial5-OCF3CH3CH35-(trifluoromethoxy)-N,N-dimethyltryptamine
120px5-Nitro-DMT{{cite journal | vauthors = Shaw E, Woolley DW | title = The synthesis of nitro-and aminoindoles analogous to serotonin. | journal = Journal of the American Chemical Society | date = April 1953 | volume = 75 | issue = 8 | pages = 1877–1881 | doi = 10.1021/ja01104a029 }}artificial5-NO2CH3CH35-nitro-N,N-dimethyltryptamine69937-13-9
120px5-CN-DMTartificial5-C≡NCH3CH35-cyano-N,N-dimethyltryptamine17380-42-6
120px5-CN-DPTartificial5-C≡NCH2CH2CH3CH2CH2CH35-cyano-N,N-dipropyltryptamine74885-19-1
120pxAlmotriptan

|artificial

| 5-(CH2SO2N(CH2)4)

| CH3

| CH3

| N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine

| 154323-57-6

120pxRizatriptan

|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

120pxSumatriptan

|artificial

| 5-(CH2SO2NHCH3)

| CH3

| CH3

| 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide

| 103628-46-2

120pxZolmitriptan

|artificial

| 5-(CHNHC=OOCH2)

| CH3

| CH3

| 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine

| 139264-17-8

120px6-Fluoro-DMTartificial6-FCH3CH36-fluoro-N,N-dimethyltryptamine1511-31-5
120px6-Fluoro-DET{{cite journal | vauthors = Rabin RA, Regina M, Doat M, Winter JC | title = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens | journal = Pharmacology, Biochemistry, and Behavior | volume = 72 | issue = 1–2 | pages = 29–37 | date = May 2002 | pmid = 11900766 | doi = 10.1016/s0091-3057(01)00720-1 | s2cid = 6480715 }}artificial6-FCH2CH3CH2CH36-fluoro-N,N-diethyltryptamine2836-69-3
120px6-Chloro-DMTartificial6-ClCH3CH36-chloro-N,N-dimethyltryptamine25390-72-1
120px6-Methyl-DMTartificial6-CH3CH3CH36,N,N-trimethyltryptamine
120px6-Hydroxy-DMTartificial6-OHCH3CH36-hydroxy-N,N-dimethyltryptamine1476-33-1
120px6-Hydroxy-DETartificial6-OHCH3CH36-hydroxy-N,N-diethyltryptamine1476-59-1
120px6-Methoxy-DMTartificial6-OCH3CH3CH36-methoxy-N,N-dimethyltryptamine2426-88-2
120px7-Methyl-DMTartificial7-CH3CH3CH37,N,N-trimethyltryptamine65882-39-5
120px7-Ethyl-DMTartificial7-CH2CH3CH3CH37-ethyl-N,N-dimethyltryptamine
120px7-Chloro-DMTartificial7-ClCH3CH37-chloro-N,N-dimethyltryptamine
120px7-Bromo-DMT{{cite journal | vauthors = Glennon RA, Schubert E, Jacyno JM, Rosecrans JA | title = Studies on several 7-substituted N,N-dimethyltryptamines | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 11 | pages = 1222–6 | date = November 1980 | pmid = 6779006 | doi = 10.1021/jm00185a014 }}artificial7-BrCH3CH37-bromo-N,N-dimethyltryptamine74798-68-8
120px7-Methoxy-DMTartificial7-OCH3CH3CH37-methoxy-N,N-dimethyltryptamine
120px7-Methoxy-MiPTartificial7-OCH3CH3CH(CH3)27-methoxy-N-methyl-N-isopropyltryptamine
120px1-Methylpsilocin

|artificial

| 1-CH3, 4-OH

| CH3

| CH3

| 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole

| 1465-16-3

120px1-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

120pxNBoc-DMT

|artificial

| 1-OCOC(CH3)3

| CH3

| CH3

| 1-(t-butoxycarbonyl)-N,N-dimethyltryptamine

|

120pxNB-5-MeO-MiPT

|artificial

| 1-OCOC(CH3)3, 5-OCH3

| CH3

| CH(CH3)2

| 1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine

|

120pxNB-5-MeO-DALT

|artificial

| 1-OCOC(CH3)3, 5-OCH3

| H2C=CH-CH2

| H2C=CH-CH2

| 1-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine

|

120px6-Fluoropsilocinartificial4-OH,6-FCH3CH34-hydroxy-6-fluoro-N,N-dimethyltryptamine312314-12-8
120px6-Fluoro-5-MeO-DMTartificial5-OCH3,6-FCH3CH35-methoxy-6-fluoro-N,N-dimethyltryptamine
120px5,6-Difluoro-EPTartificial5-F, 6-FCH2CH3CH2CH2CH35,6-difluoro-N-ethyl-N-propyltryptamine
120px5-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

120px5-Methoxy-7,N,N-trimethyltryptamine

|artificial

| 5-OCH3, 7-CH3

| CH3

| CH3

| 5-Methoxy-7,N,N-trimethyltryptamine

| 61018-77-7

120px5-Methoxy-4,N,N-trimethyltryptamine

|artificial

| 4-CH3, 5-OCH3

| CH3

| CH3

| 5-Methoxy-4,N,N-trimethyltryptamine

|

120px4-HO-5-MeO-DMT

|artificial

| 4-OH, 5-OCH3

| CH3

| CH3

| 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine

| 2433-31-0

120px4-F-5-MeO-DMT

|artificial

| 4-F, 5-OCH3

| CH3

| CH3

| 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine

| 312314-18-4

120px5-methoxy-7-fluoro-MET

|artificial

| 5-OCH3, 7-F

| CH3

| CH2CH3

| 5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine

|

120pxEMDT

|artificial

| 2-CH2CH3, 5-OCH3

| CH3

| CH3

| 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

| 263744-72-5

120pxST-1936

|artificial

| 2-CH3, 5-Cl

| CH3

| CH3

| 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine

| 1210-81-7

120pxO-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

120pxCP-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

120px4,5-DHP-DMT

|artificial

| 4,5-(OCH2CH2CH2)

| CH3

| CH3

| 1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole

| 135360-97-3

120px4,5-DHF-DMT (P-3)

|artificial{{cite patent | url = https://patents.google.com/patent/WO2023115166A1/en?oq=WO2023115166 | country = WO | number = 2023115166 | inventor = Banister S, Jorgensen W, Jinlong T | assignee = Psylo Pty Ltd. | pubdate = 29 June 2023| title = Compounds }}

| 4,5-(CH2CH2O)

| CH3

| CH3

| 2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine

|

120px4,5-Methylbenzodioxole-DMT (P-131)

|artificial

| 4,5-(OC(CH3)=N)

| CH3

| CH3

| N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine

|

120px4,5-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

120px4,5-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

120px5,6-FUR-DMT (P-4)

|artificial

| 5,6-(CH=CHO)

| CH3

| CH3

| 2-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine

|

120px5,6-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

|

120px5,6-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

|

120px5,6-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

|

class="sortbottom"

! Structure

! Short Name

! Origin

! Ring Substitution

! RN1

! RN2

! Full Name

! CAS #

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.{{cite book| vauthors = Ries RK, Miller SC, Fiellin DA |title=Principles of Addiction Medicine|url=https://books.google.com/books?id=j6GGBud8DXcC&pg=PT245|year=2009|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-7477-2|pages=216–218}}{{cite book| vauthors = Laing RR |title=Hallucinogens: A Forensic Drug Handbook|url=https://books.google.com/books?id=l1DrqgobbcwC&pg=PA102|year=2003|publisher=Academic Press|isbn=978-0-12-433951-4|pages=102–}}{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA641|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=641–}} α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life. This is analogous to α-methylation of phenethylamine into amphetamine.

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–7 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}{{cite journal | vauthors = Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB | title = Alpha-ethyltryptamines as dual dopamine-serotonin releasers | journal = Bioorganic & Medicinal Chemistry Letters | volume = 24 | issue = 19 | pages = 4754–4758 | date = October 2014 | pmid = 25193229 | pmc = 4211607 | doi = 10.1016/j.bmcl.2014.07.062 }}{{cite journal | vauthors = Nonaka R, Nagai F, Ogata A, Satoh K | title = In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes | journal = Biological & Pharmaceutical Bulletin | volume = 30 | issue = 12 | pages = 2328–33 | date = December 2007 | pmid = 18057721 | doi = 10.1248/bpb.30.2328 | doi-access = free }}{{cite journal | vauthors = Feldman JM, Chapman B | title = Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insluin secretion | journal = Diabetologia | volume = 11 | issue = 6 | pages = 487–94 | date = December 1975 | pmid = 1107123 | doi = 10.1007/bf01222097 | doi-access = free }} and produce psychostimulant, entactogen, and/or psychedelic effects. The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs. In accordance with its action as a dual releasing agent of serotonin and dopamine, αET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as αMT, 5-MeO-αMT, and various others.{{cite journal | vauthors = Huang XM, Johnson MP, Nichols DE | title = Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase) | journal = European Journal of Pharmacology | volume = 200 | issue = 1 | pages = 187–90 | date = July 1991 | pmid = 1722753 | doi = 10.1016/0014-2999(91)90686-K }}

{{Sticky}}

class="wikitable sticky-header" style="background: #FFFFFF"
Structure

! Name

! Chemical name

! CAS #

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| Tryptophan

| (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

| 73-22-3

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| 5-Hydroxytryptophan

| 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

| 4350-09-8

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| αMT

| 1-(1H-Indol-3-yl)propan-2-amine

| 299-26-3

120px

| 4-HO-αMT

| 3-(2-aminopropyl)-1H-indol-4-ol

| 15066-09-8

125px

| 4-Methyl-αMT

| 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine

| 3569-29-7

130px

| 5-Fluoro-αMT

| 1-(5-fluoro-1H-indol-3-yl)propan-2-amine

| 712-08-3

125px

| 5-Chloro-αMT

| 1-(5-Chloro-1H-indol-3-yl)propan-2-amine

| 712-07-2

120px

| 5-HO-αMT (αMS/α-methyl-5-HT)

| 3-(2-aminopropyl)-1H-indol-5-ol

| 304-52-9

120px

| 5-MeO-αMT

| 1-(5-methoxy-1H-indol-3-yl)propan-2-amine

| 1137-04-8

125px

| 5-Ethoxy-αMT

| 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine

| 101832-83-1

125px

| 5-Isopropoxy-αMT

| 1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine

|

125px

| 5-Allyloxy-αMT

| 1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine

|

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| BW-723C86

| 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine

| 160521-72-2

120px

| 6-Fluoro-αMT

| 1-(6-fluoro-1H-indol-3-yl)propan-2-amine

| 712-11-8

130px

| 7-Chloro-AMT

| 1-(7-chloro-1H-indol-3-yl)propan-2-amine

| 711-99-9

130px

| AL-37350A (4,5-dihydropyrano-αMT)

| (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole

| 362603-40-5

130px

| Compound 5 {{cite journal | vauthors = Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA | title = Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 2 | pages = 155–8 | date = January 2002 | pmid = 11755343 | doi = 10.1016/s0960-894x(01)00713-2 }}

| 1-(3H-benzo[e]indol-1-yl)propan-2-amine

|

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| αET

| 1-(1H-indol-3-yl)butan-2-amine

| 2235-90-7

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| 4-Methyl-αET

| 1-(4-Methyl-1H-indol-3-yl)butan-2-amine

| 28289-30-7

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| 4-HO-αET

| 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine

| 28289-28-3

120px

| 5-Fluoro-αET

| 1-(5-fluoro-1H-indol-3-yl)butan-2-amine

| 1380137-98-3

125px

| 5-Methyl-αET

| 1-(5-methyl-1H-indol-3-yl)butan-2-amine

| 1380148-21-9

125px

| 5-MeO-αET

| 1-(5-methoxy-1H-indol-3-yl)butan-2-amine

| 4765-10-0

130px

| 7-Methyl-αET

| 1-(7-methyl-1H-indol-3-yl)butan-2-amine

| 13712-80-6

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| 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

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| Indolylpropylaminopentane (α,N-DPT)

| 1-(1H-indol-3-yl)-N-propylpentan-2-amine

|

125px

| N,N-Dimethyl-αMT (α,N,N-TMT)

| (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine

| 4761-32-4

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| 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

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| αMDiPT

| (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine

|

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| MPMI{{cite patent | url = https://patents.google.com/patent/US5607951A | inventor = Macor JE, Wythes MJ | title = Indole derivatives | country = US | number = 5607951 | assign1 = Pfizer, Inc. | gdate = 4 March 1997 }}

| 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole

| 143321-54-4

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| Lucigenol

| (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole

| 250672-65-2

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| 5-MeO-MPMI

| 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole

| 143321-57-7

130px

| 5F-MPMI{{cite patent | url = https://patentscope.wipo.int/search/docs2/pct/WO2022256554/pdf/_n_u__KwBkKuvgReb1fxu34ELxAsVQXXErPxCV3ydgVsKtAJlK3qDiEROh20_lvaVbmbIV8FlEl4jq4Cqmvt7El-cfV1WcrU-j9V_-xiomafitvlZtBvvGcNPoGz1ArH?docId=id00000069908389 | inventor = Wallach J, Dybek M | title = Fluorinated Tryptamine Compounds, Analogues Thereof, and Methods Using Same. | country = WO | number = 2022256554 | assign1 = University Of The Sciences | pubdate = 8 December 2022 | postscript = . }}

| (R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole

|

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| 5-Br-MPMI

| 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole

| 143322-57-0

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| Eletriptan

| 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole

| 143322-58-1

130px

| Z5247692566{{cite journal | vauthors = Callaway E |title=AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery? |journal=Nature News |date=18 January 2024 |volume=626 |issue=7997 |pages=14–15 |doi=10.1038/d41586-024-00130-8|pmid=38238624 |bibcode=2024Natur.626...14C |s2cid=267040499 }}

| 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine

|

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| BK-NM-AMT (α,N-dimethyl-β-ketotryptamine){{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 | url = }}{{cite web | title=1-(1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/82282492 | access-date=11 November 2024}}{{cite patent | country = US | number = 20240335414 | invent1 = Matthew J. Baggott | invent2 = Sean Dalziel | assign = Tactogen Inc. | title=Specialized combinations for mental disorders or mental enhancement | url=https://patents.google.com/patent/US20240335414A1/ | pubdate = 10 October 2024 }}

| 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one

|

130px

| BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine){{cite web | title=1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162765676 | access-date=11 November 2024}}{{cite web | title=β-Oxo-5-fluoro-α-methyl-NMT | website=Isomer Design | date=10 November 2024 | url=https://isomerdesign.com/pihkal/explore/12714 | access-date=11 November 2024}}{{cite patent | country = WO | number = 2022061242 | inventor = Matthew Baggott | status = | title = Advantageous tryptamine compositions for mental disorders or enhancement | pubdate = 2023 March 24 | gdate = | fdate = 2021 September 20 | pridate = 2021 September 20 | assign1 = Tactogen | url = https://patents.google.com/patent/WO2022061242A1/}}

| 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one

|

130px

| BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine){{cite web | title=1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162765502 | access-date=11 November 2024}}{{cite web | title=β-Oxo-5-chloro-α-methyl-NMT | website=Isomer Design | date=10 November 2024 | url=https://isomerdesign.com/pihkal/explore/12715 | access-date=11 November 2024}}

| 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one

|

130px

| BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine){{cite web | title=1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162765532 | access-date=11 November 2024}}{{cite web | title=β-Oxo-5-bromo-α-methyl-NMT | website=Isomer Design | date=10 November 2024 | url=https://isomerdesign.com/pihkal/explore/12725 | access-date=11 November 2024}}

| 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. 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. They act as monoamine releasing agents.

Cyclized tryptamines

Examples of cyclized tryptamines include:

Related compounds

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.

{{Sticky}}

class="wikitable sticky-header" style="background: #FFFFFF"
Structure

! Name

! Chemical name

! CAS #

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| C-DMT{{cite web | title=PiHKAL·info | website=Isomer Design | date=11 November 2024 | url=https://isomerdesign.com/pihkal/explore/5070 | access-date=31 January 2025}}

| 2-(3H-inden-1-yl)-N,N-dimethylethanamine

|

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| Dimemebfe

| 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine

| 140853-58-3

120px

| 5-MeO-DiBF

| N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

|

120px

| 3-APB

| 3-(2-aminopropyl)benzofuran

| 105909-13-5

120px

| 3-APBT

| 1-(1-benzothiophen-3-yl)propan-2-amine

| 1201-27-0

120px

| Mebfap

| 3-(2-aminopropyl)-5-methoxybenzofuran

| 140853-59-4

120px

| Isotryptamine

| 2-indol-1-ylethanamine

| 13708-58-2

120px

| isoAMT

| 1-indol-1-ylpropan-2-amine

| 1227465-67-9

| (S)-5,6-Difluoro-isoAMT {{cite journal | vauthors = Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA | title = Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors | journal = Bioorg Med Chem Lett | volume = 12 | issue = 2 | pages = 155–158 | date = January 2002 | pmid = 11755343 | doi = 10.1016/s0960-894x(01)00713-2 | url = | quote = Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e., S(+)-5,6-difluoro-α-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best, only 10-fold.}}

| (S)-1-(5,6-difluoroindol-1-yl)propan-2-amine

|

120px

| Ro60-0175

| (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine

| 169675-09-6

120px

| isoDMT

| 2-indol-1-yl-N,N-dimethylethanamine

| 87482-09-5

120px

| 5-MeO-isoDMT

| 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine

| 244122-80-3

120px

| 6-MeO-isoDMT

| 2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine

| 87482-11-9

120px

| Zalsupindole (DLX-001; AAZ-A-154)

| (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine

| 2481740-94-5

120px

| 2ZEDMA

| 2-indolizin-1-yl-N,N-dimethylethanamine

|

120px

| 1ZP2MA

| 1-indolizin-1-yl-N-methylpropan-2-amine

|

120px

| 1Z2MAP1O

| 1-indolizin-3-yl-2-(methylamino)propan-1-one

| 2110204-31-2

120px

| Example 16 Kargbo RB. Neuropharmacological Advances: Harnessing 5-HT2A Receptor Modulators and Psychoplastogens. ACS Med Chem Lett. 2024 Jan 23;15(2):171-173. {{doi|10.1021/acsmedchemlett.4c00003}} {{PMID|38352827}}[https://patents.google.com/patent/WO2023114844A1 Powell NA, Chytil M. Imidazopyridine psychoplastogens and uses thereof. WO 2023/114844]

| 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine

|

120px

| Example 1 {{cite patent |country= US |number= 7012090|status= granted |title= Pyranoindoles for treating glaucoma |pubdate= 17 March 2000 |gdate= 14 March 2006 |fdate= |pridate= |inventor= Chen HH, May JA |assign1= Alcon, Inc. }}

| 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine

|

120px

| VER-3323

| (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine

| 259857-99-3

120px

| AL-34662

| 1-((S)-2-Aminopropyl)-1H-indazol-6-ol

| 210580-75-9

120px

| O-Methyl-AL-34662

| 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole

| 210580-60-2

120px

| 7-methyl-AL-34662

| 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol

| 874668-67-4

120px

| 7-chloro-AL-34662

| 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol

| 874881-86-4

120px

| AL-38022A

| (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine

| 478132-11-5

120px

| Example 9 {{cite patent |country= US |number= 6881749|status= granted |title= Pyranoindazoles and their use for the treatment of glaucoma|pubdate= 3 June 2004 |gdate= 19 April 2005 |fdate= |pridate= |inventor= Chen HH, May JA, Severns BS |assign1= Alcon, Inc. }}

| (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine

| 478132-12-6

120px

| Example 3 {{cite patent |country= US |number= 7425572 |status= granted |title= Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma|pubdate= 8 June 2006 |gdate= 16 September 2008 |fdate= |pridate= |inventor= Chen HH, May JA |assign1= Alcon, Inc.}}

| (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine

| 890087-75-9

120px

| Example 1 {{cite patent |country= US |number= 7268131|status= granted |title= Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma |pubdate= 15 December 2005 |gdate= 11 September 2007 |fdate= |pridate= |inventor= |invent1= Dantanarayana AP, May JA |assign1= Alcon, Inc. }}

| (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine

| 1373917-69-1

120px

| YM-348

| (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine

| 372163-84-3

120px

| 2-desethyl-YM-348 {{cite journal | vauthors = Shimada I, Maeno K, Kazuta K, Kubota H, Kimizuka T, Kimura Y, Hatanaka K, Naitou Y, Wanibuchi F, Sakamoto S, Tsukamoto S | display-authors = 6 | title = 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 | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 4 | pages = 1966–82 | date = February 2008 | pmid = 18035544 | doi = 10.1016/j.bmc.2007.10.100 }}

| (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine

| 748116-94-1

120px

| I-32 {{cite patent | url = https://patentscope.wipo.int/search/docs2/pct/WO2022120475/pdf/uj8ks7KeBwfyrcKyh46zk14uREF4Bj7Trj6KlQ-oUEt-C_bGCaxuitXf82w1XlNPy1_QtiCTsXAk9lPBgdPNKrIsDWGJA326j7ulFZ3R1QP95os0XOWgsfGAtmOfFlKR?docId=id00000066831129&filename=WO2022120475-PAMPH-20220616-1129.pdf | inventor = Slassi A, Araujo J, Higgins G | title = 3-Cyclic Amine-Indole Derivatives as Serotonergic Agents for the Treatment of CNS Disorders. | country = WO | number = 2022120475 | assign = Mindset Pharma Inc. | pubdate = 16 June 2022 }}

| 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol

|

120px

| 2-Azapsilocin (Psilocin indazole analogue, P-6){{cite patent | url = https://patents.google.com/patent/WO2023115165A1/en?oq=WO2023115165 | country = WO | number = 2023115165 | inventor = Banister S, Jorgensen W, Jinlong T | title = Compounds | assignee = Psylo Pty Ltd. | pubdate = 29 June 2023 }}

| 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol

|

120px

| 4-Aza-5-MeO-DPT (P-11)

| N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine

|

120px

| 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

|

120px

| 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

|

120px

| RS134-49

| 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole

| 2945139-94-4

120px

| RU-28253

| 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole

|

120px

| VU6067416Jayakodiarachchi N, et al. Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists. ACS Med. Chem. Lett. 2024 {{doi|10.1021/acsmedchemlett.3c00566}}

| 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole

| 3027515-24-5

120px

| (R)-69

| 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine

| 2765652-48-8

120px

| SN-22

| 3-(1-methylpiperidin-4-yl)-1H-indole

| 17403-07-5

120px

| RU-24,969

| 5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole

| 107008-28-6

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| EMD-386088

| 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

| 54635-62-0

Tryptamine-based therapeutics

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!Drug

!Mechanism

!Treatment

!Effect

!Structure

Sumatriptan{{Citation|title=Serotonin Receptor Agonists (Triptans)|date=2012|url=http://www.ncbi.nlm.nih.gov/books/NBK548713/|work=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury|place=Bethesda (MD)|publisher=National Institute of Diabetes and Digestive and Kidney Diseases|pmid=31644023|access-date=2020-10-15}}

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

Rizatriptan

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

Zolmitriptan

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

Almotriptan

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

Eletriptan

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

Frovatriptan

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

Naratriptan

|5-HT1B and 5-HT1D agonist

|Migraine headaches

|Vasoconstriction of brain blood vessels

|200px

See also

=Categories=

References

{{Reflist|2}}

{{Tryptamines}}

{{Psychedelics}}

{{Serotonergics}}

{{Chemical classes of psychoactive drugs}}

Category:Tryptamines

Category:Alpha-Alkyltryptamines

Category:Chemical classes of psychoactive drugs

Category:Functional groups