Substituted tryptamine

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.[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.[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.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.
The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN 1 =RN 2 =Rα = H.
The structure of substituted tryptamines with all positions labeled.
Sumatriptan
Rizatriptan
Zolmitriptan
Almotriptan
Eletriptan
Frovatriptan
Naratriptan
organic compoundstryptamineindoleamino (NH2) groupsidechainserotoninneurotransmittermelatoninhormonealkaloidsplantsanimalshumanspsychotropicpsilocybinpsilocybin mushroomschacrunaayahuascasyntheticmigrainesumatriptanpsychedelic drugsibogainemitragynineyohimbineAlexander ShulginTiHKAL2-HO-NMT5-MeO-NMTNω-MethylserotoninBufoteninBufotenidineO=C-CH3N-Acetylserotonin6-Hydroxymelatonin4-HO-NMTPsilocinNorbaeocystinBaeocystinAeruginascinLespedamine5-MeO-DMT5-Bromo-DMT6-Bromotryptamine5,6-Dibromotryptamine5,6-Dibromo-NMT5,6-Dibromo-DMTDesformylflustrabromineConvolutindole AAcetryptine5-(Nonyloxy)tryptamine2-Methyl-5-hydroxytryptamine5-MeO-T-NBOMe5-MeO-NBpBrTIdalopirdine4-HO-pyr-T5-MeO-pyr-TCH2CH2CH3CH(CH3)2H2C=CH-CH22-Methyl-DMT2-Me-DET4-MeO-DMT4-MeO-MiPT4-AcO-DMT4-PrO-DMT4-HO-MET4-Acetoxy-MET4-HO-DET4-Acetoxy-DET4-PO-DET4-HO-EPT4-HO-MPT4-HO-MiPT4-Acetoxy-MiPT4-HO-MALT4-HO-NALT4-HO-EiBT4-HO-McPT4-HO-McPeT4-HO-DPT4-AcO-DPT4-HO-PiPT4-HO-DIPT4-Acetoxy-DiPTFT-1044-AcO-DALT4-HO-DBT4-HO-DSBT5-MeO-MET5-MeO-DET5-MeO-EPT5-MeO-DPT5-MeO-MALT5-MeO-DALT5-MeO-MiPT5,6-MeO-MiPT5-MeO-EiPT5-MeO-PiPT5-MeO-DIPT5-MeO-DBT5-MeS-DMT5-AcO-DMT5-Ethoxy-DMT5-HO-DiPT5,N,N-TMT5-Ethyl-DMT5-Fluoro-DMT5-Fluoro-MET5-Fluoro-DET5-Fluoro-EPT5-Chloro-DMT5-TFM-DMT5-TFMO-DMT5-Nitro-DMTAlmotriptanRizatriptanZolmitriptan6-Fluoro-DMT6-Fluoro-DET7-Methyl-DMT1-MethylpsilocinNBoc-DMT5-MeO-2-TMT5-Methoxy-7,N,N-trimethyltryptamine4-HO-5-MeO-DMT4-F-5-MeO-DMT5-methoxy-7-fluoro-METST-1936O-4310CP-132,4844,5-DHP-DMT4,5-MDO-DMT4,5-MDO-DiPT5,6-MDO-DMT5,6-MDO-MiPT5,6-MDO-DiPTalkyl groupmethylalpha carbonmetabolically stablemonoamine oxidasepotencyhalf-lifephenethylamineamphetaminemonoamine releasing agentsserotonin receptor agonistsmonoamine oxidase inhibitorspsychostimulantentactogenpsychedelicα-methyltryptamineα-ethyltryptamineantidepressantsabusedrecreational drugsreleasing agentdopamineserotonergicneurotoxicityamphetamines5-MeO-αMTTryptophan5-Hydroxytryptophan4-HO-αMT4-Methyl-αMT5-Fluoro-αMT5-Chloro-αMT5-HO-αMT5-Ethoxy-αMTBW-723C866-Fluoro-αMT7-Chloro-AMTAL-37350A4-Methyl-αET5-Fluoro-αET5-MeO-αET7-Methyl-αETN-Methyl-5-MeO-αMTIndolylpropylaminopentaneN,N-Dimethyl-αMTN,N-Dimethyl-5-MeO-αMTLucigenol5-MeO-MPMI5F-MPMIEletriptanBK-NM-AMTβ-ketotryptaminescathinonesisotryptaminesindeneindolineindazoleindolizinebenzothiophenebenzofuranglaucomacluster headachesanorecticsDimemebfe5-MeO-DiBF3-APBTIsotryptamineisoAMTRo60-0175isoDMT5-MeO-isoDMT6-MeO-isoDMTAAZ-A-1542ZEDMA1ZP2MA1Z2MAP1OVER-3323AL-34662AL-38022AYM-348VU6067416(R)-695-HT1B5-HT1DVasoconstrictionFrovatriptanNaratriptanErgolineLysergamideIboga alkaloidSubstituted amphetamineSubstituted benzofuranSubstituted cathinoneSubstituted methylenedioxyphenethylamineSubstituted phenethylamineList of miscellaneous 5-HT2A receptor agonistsBibcodeSerotonin receptormodulators5-HT1A8-OH-DPATAdatanserinetoperidonehydroxynefazodonenefazodonetrazodonetriazoledionevilazodonevortioxetineAtypical antipsychoticsaripiprazoleasenapinebrexpiprazolecariprazineclozapinelurasidonequetiapineziprasidoneAzapironesbuspironeeptapironegepironeperospironetandospironeBay R 1531BefiradolBMY-14802CannabidiolEbalzotanEltoprazineEnciprazineErgolinesbromocriptinecabergolinedihydroergotamineergotaminelisuridemethylergometrine 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(ergonovine)AnpirtolineCGS-12066ACP-93129CP-94253CP-122,288CP-135807TriptansavitriptandonitriptanAR-A000002ElzasonanGR-127935LY-393558SB-216641SB-236057L-694247PNU-1426335-Et-DMTAlniditanBRL-15,572KetanserinLY-310762LY-367642LY-456219LY-456220MianserinRitanserinlysergol5-HT1EBRL-544435-HT1FLasmiditanLY-3343705-HT2A25I-NBF25I-NBMD25I-NBOH25I-NBOMe25B-NBOMe25C-NBOMe25TFM-NBOMe2CBCB-NBOMe25CN-NBOH2CBFly-NBOMe2C-T-22C-T-72C-T-212C-B-FLY2CB-Ind5-Methoxytryptaminesα-Alkyltryptamines5-Cl-αMT5-Fl-αMTα-Me-5-HTBromo-DragonFLYDMBMPPEfavirenz1P-LSDALD-52ergine (LSA)LA-SS-AzLSD-PipIHCH-7113JimscalineLorcaserinMDA (tenamfetamine)MDMA (midomafetamine)PHA-57378PNU-22394PNU-181731SCHEMBL5334361PhenethylamineslophophinemescalinePiperazinesquipazineTFMFly5-I-R91150AC-90179AltanserinAntihistaminescyproheptadinehydroxyzineketotifenperlapineamperozideblonanserincarpipramineclocapramineclorotepinefluperlapinegevotrolinemelperonemosapramineocaperidoneolanzapinepaliperidonezicronapinezotepineChlorprothixeneCinanserinDeramciclaneEplivanserinamesergideLY-215,840mesulerginesergolexoleFananserinGlemanserinKML-010MedifoxamineNaftidrofurylNantenineNelotanserinOpiranserin (VVZ-149)PelanserinPhenoxybenzaminePimavanserinPirenperonePizotifenPruvanserinRoluperidoneSarpogrelateSerotonin antagonists and reuptake inhibitorslubazodonemepiprazoleTeniloxazineTetracyclic antidepressantsamoxapineaptazapineesmirtazapinemaprotilinemirtazapineTricyclic antidepressantsamitriptylineTypical 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(MDL-72222)BupropionCilansetronDazoprideDolasetronGalanolactoneGranisetronHydroxybupropionLerisetronMemantineOndansetronPalonosetronRamosetronRenzaprideRicasetronThujoneTropanserinTropisetronnitrous oxidesevofluraneZacoprideZatosetronnaphthylpiperazineCapeserodCinitaprideCisaprideCJ-033466MetoclopramideMosapridePrucalopridePRX-03140RS-67,333VelusetragGR-113808L-LysinePiboserodSB-2040705-HT5A2-Br-LSD (BOL-148)Valerenic acidSB-699551E-6801E-6837EMD-386088WAY-181187WAY-208466tiospironeAVN-101AVN-211AVN-322AVN-397CerlapirdineEGIS-12,233MasupirdineMS-245PRX-07034Ro 04-6790SB-258585SB-271046SB-357134SB-399885SB-742457clomipraminedoxepinlergotrileBifeprunoxE-55888LP-211ButaclamolDR-4485JNJ-18038683SB-258719SB-269970imipramineacetophenazine2-Methyl-5-HT2,N,N-TMT4-AcO-DET4-AcO-DiPT4-AcO-MET4-AcO-MiPT4-HO-TMT5-HTP (oxitriptan)5-MeO-7,N,N-TMT5-MeO-T (5-MT; mexamine)5-Methyl-DMT5-Methyl-T5,6-DHT5,7-DHT6-MeO-DMTAcetryptine (5-AT)Aeruginascin (4-PO-TMT)AGH-107AGH-192AH-494AlpertineBaeocystin (4-PO-NMT)Benzotript (4-chlorobenzoyl-L-tryptophan)Bufotenin (5-HO-DMT)Ethocybin (4-PO-DET)FGIN-127FGIN-143Iprocin (4-HO-DiPT)IsamideMilipertineMiprocin (4-HO-MiPT)N-Feruloylserotonin (moschamine)NET/NETPNorbaeocystin (4-PO-T)O-PivalylbufotenineOxypertinePsilacetin (O-acetylpsilocin; 4-AcO-DMT)Psilocin (4-HO-DMT)Psilocybin (4-PO-DMT)RS134-49SolypertineTryptamine (T)YuremamineN-Acetyltryptamines2-Iodomelatoninα-MethylmelatoninLuzindoleNormelatonin (N-acetylserotonin; NAS)N-AcetyltryptaminePiromelatine2,α-DMT4-HO-MPMI (lucigenol)4-Me-αET4-Me-αMT5-Chloro-αET5-MeO-α,N,N-TMT5-MeO-αET 7-Chloro-αMTα-Methyl-5-HTPα-Methylserotonin (5-HO-αMT)α-Methyltryptophan (αMTP)α,N-DMT (N-methyl-αMT)α,N,N-TMTα,N,O-TMSαET (etryptamine)AL-37350A (4,5-DHP-αMT)BNC-210IPAP (α,N-DPT)Cyclized tryptaminesCiclindoleCyclic 3-OHMlysergamidesFlucindoleHarmala alkaloidsβ-carbolines6-MeO-THH9-Me-BCβ-carboline (norharman)harmalineharmalolharmaneharminepinolinetetrahydroharminetryptolineIboga alkaloidsDM-506 (ibogaminalog)ibogaminenoribogainetabernanthalogtabernanthineLY-266,097MetralindoleRU-28306YohimbansspegatrinecorynanthineajmalicinereserpinedeserpidinerescinnamineAAZ-A-154 (DLX-001)Isotryptamine (isoT)5-HIAA5-HIALBenzofuransLatrepirdineLY-367265Pirlindole(R)-69 (3IQ)TepirindoleTetrindole