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5,N,N-TMT

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

5,N,N-TMT
Clinical data


Other names	5,N,N-Trimethyltryptamine; 5,N,N-TMT; 5-TMT; 5-Methyl-N,N-dimethyltryptamine; 5-Methyl-DMT; 5-Me-DMT
ATC code	None
Identifiers
IUPAC name (2-(5-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine
CAS Number	22120-39-4^Y
PubChemCID	1837
ChemSpider	1771^Y
UNII	HIX0SK1CCX
CompTox Dashboard(EPA)	DTXSID30176641
ECHA InfoCard	100.164.424
Chemical and physical data
Formula	C₁₃H₁₈N₂
Molar mass	202.301 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1c(ccc2c1c(c[nH]2)CCN(C)C)C
InChI InChI=1S/C13H18N2/c1-10-4-5-13-12(8-10)11(9-14-13)6-7-15(2)3/h4-5,8-9,14H,6-7H2,1-3H3^Y Key:NCGJLYBZSJSCIC-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

5,N,N-Trimethyltryptamine (5,N,N-TMT;5-TMT), also known as5-methyl-DMT, is atryptamine derivative that may be apsychedelic drug. It was first made in 1958 by Edwin H. P. Young.^[1] In animal experiments it was found to be in betweenDMT and5-MeO-DMT in potency.^[2]^[3]

Chemistry

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Analogues

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Analogues of 5,N,N-TMT includedimethyltryptamine (DMT),5-methyltryptamine,5-ethyl-DMT,5-MeO-DMT,5-fluoro-DMT,5-chloro-DMT,5-bromo-DMT,1-methyl-DMT,2-methyl-DMT,4-methyl-DMT,6-methyl-DMT, and7-methyl-DMT, among others.

Society and culture

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Legal status

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United States

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5,N,N-TMT is not scheduled at the federal level in theUnited States,^[4]^[5] but it could be considered an analog of5-MeO-DMT, in which case, sales or possession intended for human consumption could be prosecuted under theFederal Analog Act.

References

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^Young EH (1958). "704. The synthesis of 5-hydroxytryptamine (serotonin) and related tryptamines".Journal of the Chemical Society (Resumed):3493–6.doi:10.1039/JR9580003493.
^Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues".Journal of Medicinal Chemistry.22 (4):428–32.doi:10.1021/jm00190a014.PMID 430481.
^Glennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities".Psychopharmacology.68 (2):155–8.doi:10.1007/BF00432133.PMID 6776558.S2CID 1674481.
^"§ 1308.11 Schedule I." Archived fromthe original on 2009-08-27. Retrieved2014-12-17.
^"§ 1308.11 Schedule I."e-CFR. 2022-02-17.Archived from the original on 2022-02-10.

External links

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Psychedelics

Tryptamines

No ring subs.	CYB004 (deuDMT) DALT DBT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT McPT MET MiPT MPT NMT PALT PiPT SPL028 (D₂-DMT) Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-NBnT 4-HO-NET 4-HO-NiPT 4-HO-NPT 4-HO-TMT 4-HO-5-MeO-DMT 4-HO-T (4-HT) 4-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines:Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acyloxytryptamines:4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET Luvesilocin (4-GO-DiPT; RE-104, FT-104)
5-Hydroxytryptamines	5-HO-MET Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acyloxytryptamines:O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NiPT 5-MeO-NMT 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MeO-T (5-MT) ASR-3001 (5-MeO-iPALT) NB-5-MeO-DALT NB-5-MeO-MiPT
Other ring subs.	2,N,N-TMT (2-methyl-DMT) 4,N,N-TMT (4-methyl-DMT) 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-PhO-T (OVT2) 5-N,N-TMT (5-methyl-DMT) 7,N,N-TMT (7-methyl-DMT) 5-MeO-2,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) Bretisilocin (GM-2505; 5-fluoro-MET) NBoc-DMT (NB-DMT)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) α,N,N-TMT (α-Me-DMT; Alpha-N) N-Hydroxy-AMT 5-Methoxy-α-alkyltryptamines:5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g.,N-DEAOP-NET,N-DEAOP-NMT,5-MeO-N-DEAOP-NMT,5-MeO-N-DEAOP-NET) Structure undisclosed:CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g.,LSD) Ibogalogs (e.g.,ibogainalog,tabernanthalog) O-Methylnordehydrobufotenine Partial ergolines (e.g.,NDTDI,RU-28306,CT-5252) Piperidinylethylindoles (e.g.,pip-T) Pyrrolidinylethylindoles (e.g.,pyr-T,5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5-MeO-MPMI,MSP-2020) Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI),NEtPhOH-THPI)
Bioisosteres	Benzofurans (e.g.,5-MeO-DiBF (1-oxa-5-MeO-DiPT),dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT),mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT)) Benzothiophenes (e.g.,3-APBT (1-thia-AMT)) Indazolethylamines (e.g.,AL-38022A,O-methyl-AL-34662) Indenylethylamines (e.g.,C-DMT) Isotryptamines (e.g.,6-MeO-isoDMT,Ro60-0175) MYCO-005 Quinolinylethylamines (e.g.,mefloquine)

Phenethylamines

Scalines	2-Bromomescaline 4-D (4-trideuteromescaline) 4-Desoxymescaline (desoxy) Allylescaline (AL) Beta-D (β-D; β-dideuteromescaline) Cyclopropylmescaline (CPM) Difluoroescaline (DFE) Difluoromescaline (DFM) N,N-Diformylmescaline Escaline (E) Fluoroescaline (FE) Fluoroproscaline (FP) N-Formylmescaline Isobuscaline (IB) Isoproscaline (IP) Jimscaline Mescaline (M; 3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline (ME) Methallylescaline (MAL) N-Methylmescaline (M-M) Proscaline (P) Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline (TFE) Trifluoromescaline (TFM) Thioscalines:3-Thioasymbescaline (3-TASB) 3-Thioescaline (3-TE) 3-Thiomescaline (3-TM) 3-Thiometaescaline (3-TME) 4-Thioasymbescaline (4-TASB) 4-Thioescaline (4-TE) 4-Thiomescaline (4-TM) 5-Thioasymbescaline (5-TASB) Thiobuscaline (TB; 4-TB) Thioproscaline (TP; 4-TP)
2C-x	2C-B 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-P 2C-Se 2C-Se-TFM 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x:2C-T 2C-T-2 2C-T-3 (2C-T-20) 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-21.5 2C-T-22 2C-T-25 2C-T-27 2C-T-28 2C-T-30 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x:2C-O (2,4,5-TMPEA; TMPEA-2) 2C-O-4 2C-O-22 Others:2C-B-AN 2C-DB 2C-G-x (e.g.,2C-G-3,2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g.,BOB,BOD,BOHB) HOT-x (e.g.,HOT-2,HOT-7,HOT-17) N-Ethyl-2C-B TWEETIOs (e.g.,2CB-2-EtO,2CD-2-EtO,2CD-5-EtO,2CE-5-EtO,2CE-5iPrO,2CT2-5-EtO,ASR-2001 (2CB-5-PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA (3C-M)
DOx	DOAM DOB DOBU DOC DOEF DOET DOH (2,5-DMA) DOI DOIB DOIP DOM DON DOPR DOTFM DOYN Aleph-x (DOT-x):Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx):MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others:DODB DODC DOM-NBOMe DOTMA Ganeshas (G-x) (e.g.,Ganesha (G, G-0),G-3,G-5) N-Hydroxy-DOM
4C-x	4C-B 4C-D (Ariadne) 4C-I 4C-P (4C-Pr) 4C-T-2 4C-TFM
Ψ-PEA	2,4,6-TMPEA-NBOMe Ψ-2C-DFMO (ψ-2C-O-35) Ψ-2C-T-4 Ψ-DODFMO Ψ-DOM TMA-6 (Ψ-TMA-2)
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA EMDA-2 IDA Lophophine (MMDPEA) Lys-MDA MDA (tenamfetamine) MDHMA (FLEA; MDMOH) MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDA-3b MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly Hemi/semi-FLY drugs:2CB-5-hemiFLY DOH-5-hemiFLY (semi-fly; SF) DOB-5-hemiFLY (bromo-semi-fly; B-SF)
25x-NB (NBOMes)	25x-NBOMe:25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25O-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH:25B-NBOH 25C-NBOH 25CN-NBOH 25E-NBOH 25I-NBOH Others:2,4,6-TMPEA-NBOMe 25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027
Others	25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM Benzofurans (e.g.,5-APB,5-APDB,6-APB,6-APDB,F,F-2,F-22) Benzothiophenes (e.g.,5-APBT,6-APBT) CT-5172 DMAs (e.g.,2,4-DMA,3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g.,25D-NM-NDEAOP,DOB-NDEPA,DOI-NDEPA,DOM-NDEPA,DOTFM-NDEPA,M-NDEPA,TMA-2-NDEPA) PMA (4-MA) Thio-2Cs (e.g.,2C-5-TOET) Thio-DOx (e.g.,2-TOM,5-TOET,5-TOM,TOMSO) TMAs (e.g.,TMA-3,TMA-4,TMA-5) ZDCM-04 (DOC-fenethylline) Structure undisclosed:CYB005
Cyclized	1-Aminomethylindanes (e.g.,2CB-Ind,jimscaline) 2-Aminoindanes (e.g.,DOM-AI) 3-Benzazepines (e.g.,lorcaserin) 3-Phenylpiperidines (e.g.,LPH-5,LPH-48) Benzocyclobutenes (e.g.,2CBCB-NBOMe,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g.,LSD) Glaucine Partial ergolines (e.g.,NDTDI,DEIMDHPCA,DEMPDHPCA,DEMTMPDHPCA,DEMNDHPCA) Phenylcyclopropylamines (e.g.,DMCPA,TMT) Phenyloxazolamines (aminorexes) (e.g.,2C-B-aminorex) Pyridopyrroloquinoxalines (e.g.,IHCH-7113) Z3517967757 ZC-B

Lysergamides

No substitutions:Ergine (LSA, LA-111)
Isoergine (iso-LSA, iso-LA)

1-Alkyllysergamides (prodrugs):Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

1-Acyllysergamides (prodrugs):1-Formyl-LSD
1B-LSD
1BP-LSD
1Bz-LSD
1cP-AL-LAD
1cP-LSD
1cP-MiPLA
1D-AL-LAD
1D-LSD
1DD-LSD
1F-LSD
1Fe-LSD
1H-LSD
1P-AL-LAD
1P-ETH-LAD
1P-LSD
1P-MiPLA
1S-LSD
1SB-LSD (1BS-LSD)
1T-AL-LAD
1T-LSD
1V-LSD
ALA-10 (1-acetyl-LAE; 1A-LAE)
ALD-52 (1-acetyl-LSD; 1A-LSD)

Bioisosteres:JRT (isoindole-LSD)

Others

Arylpiperazines (e.g.,2C-B-PP,2-NP,mCPP,MK-212,ORG-12962,pCPP,pFPP,quipazine,TFMPP)
Dihydrobenzoxazines (e.g.,efavirenz)
Phenoxyethylamines (e.g.,CT-4719,ORG-37684)
Pyridopyrroloquinoxalines (e.g.,IHCH-7113)
Quinazolinylethylamines (e.g.,RH-34)

Natural sources

Phenethylamines:Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Echinopsis cacti (e.g.,San Pedro,Peruvian torch)

v t e Tryptamines
Tryptamines	1-Methyl-DMT (1,N,N-TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N,N-TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T) N-DEAOP-NET N-DEAOP-NMT NAT NBoc-DMT (NB-DMT) NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 Zolmitriptan
4-Hydroxytryptamines andesters/ethers	1-Methylpsilocin (CMY-16) 4-AcO-DALT 4-AcO-DET (ethacetin, ethylacybin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin;O-acetylpsilocin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiBT 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-DsBT 4-HO-EiBT (eibucin) 4-HO-EiPT 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-MET (metocin) 4-HO-McPT 4-HO-McPeT 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-NALT 4-HO-NBnT 4-HO-NcHT 4-HO-NET 4-HO-NiPT 4-HO-NBT (4-HO-NnBT) 4-HO-NPT 4-HO-NtBT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DET 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) EB-002 (EB-373) Ethocybin (4-PO-DET; CEY-19) Luvesilocin (4-GO-DiPT; RE-104; FT-104) MSP-1014 Norbaeocystin (4-PO-T) Norpsilocin (4-HO-NMT) O-4310 (1-iPrO-6-F-psilocin) Psilocin (4-HO-DMT; CX-59) Psilocybin (4-PO-DMT; CY-39) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) RE-109 (4-GO-DMT)
5-Hydroxy- and 5-methoxytryptamines	2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N,N,O-TMS;O-methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O-methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ;N,N,N-TMS) Bufotenin (5-HO-DMT;N,N-DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) NB-5-MeO-DALT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT)
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin (N-Ac-O-Me-serotonin;N-Ac-5-MeO-T) Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301 (LY-156735)
α-Alkyltryptamines	1-Methyl-AMT 2,α-DMT (2-Me-AMT) 4-HO-αET 4-HO-αMT (MP-14) 4-Methyl-αET 4-Methyl-αMT (MP-809) 5-Chloro-αET (PAL-526) 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212; PAL-544) 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Me-αET α-Methyltryptophan (αMTP) α,N-DMT (N-Me-αMT; SKF-7024, Ro 3-1715) α,N,N-TMT (α-Me-DMT; Alpha-N) αET (etryptamine; Monase) αMT (Indopan; IT-290; 3-API; 3-IT) IPAP (α,N-DPT) N-Hydroxy-AMT Soclenicant (BNC-210; Ile–Trp) 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines:1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O-DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 β-Keto-α-alkyltryptamines:BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT
α-Ketotryptamines	AB-CHMIATA ADB-FUBIATA (ADB-FUBIACA) ADB-IACA AFUBIATA CH-FUBIATA (CH-FUBIACA) CH-HEXIATA CH-IACA CH-PIATA CH-PIATAN-(4-carboxybutyl) CH-PIATAN-(4-hydroxypentyl) CHM-FUBIATA
Cyclized tryptamines	5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD) Harmala alkaloids andβ-carbolines (e.g.,5-methoxyharmalan,6-MeO-THH,6-methoxyharmalan,9-Me-BC,β-carboline (norharman),fenharmane,harmaline,harmalol,harmane,harmine,LY-266,097,pinoline,tetrahydroharmine,tryptoline) Iboga alkaloids (e.g.,ibogaine,ibogamine,noribogaine,tabernanthine) Ibogalogs (e.g.,catharanthalog,fluorogainalog,ibogainalog,ibogaminalog (DM-506),LS-22925,noribogainalog,noribogaminalog,PHA-57378,PNU-22394,tabernanthalog) Imidazolylindoles (e.g.,AGH-107,AGH-192,AH-494) Metralindole Morpholinylethylindoles (e.g.,mor-T,5-MeO-mor-T) Partial ergolines and lysergamides (e.g.,NDTDI,RU-27849,RU-28251,RU-28306,FHATHBIN,LY-178210,Bay R 1531 (LY-197206),LY-293284,10,11-seco-LSD,10,11-secoergoline (α,N-Pip-T),CT-5252) Pertines (e.g.,alpertine,milipertine,oxypertine,solypertine) Piperidinylethylindoles (e.g.,pip-T,5-MeO-pip-T,indolylethylfentanyl) Pyrrolidinylethylindoles (e.g.,pyr-T,4-HO-pyr-T,5-MeO-pyr-T,4-F-5-MeO-pyr-T,L-760790) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5F-MPMI,5-MeO-MPMI,CP-122288,CP-135807,eletriptan,MSP-2020) Tetrahydrocarbazolamines (e.g.,ciclindole,flucindole,frovatriptan,LY-344864,ramatroban) Tetrahydropyridinylindoles (e.g.,RS134-49,RU-28253,NEtPhOH-THPI) Tetrahydropyrroloquinolines (e.g.,bufothionine,O-methylnordehydrobufotenine,dehydrobufotenine) Yohimbans (e.g.,yohimbine,rauwolscine,spegatrine,corynanthine,ajmalicine,reserpine,deserpidine,rescinnamine)
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT (1-API; 1-IT; α-Me-isoT) isoDMT Isotryptamine (isoT) Ro60-0175 VER-3323 Zalsupindole (DLX-001, AAZ-A-154) Cyclized isotryptamines:JRT PNU-181731
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline,alosetron,gevotroline,latrepirdine,lurosetron,mebhydrolin,tiflucarbine) Amedalin Benzindopyrine Benzofurans (e.g.,3-APB (1-oxa-AMT),5-MeO-DiBF (1-oxa-5-MeO-DiPT),BPAP,3-F-BPAP,dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT),mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT),MiPBF (1-oxa-MiPT),oxa-noribogaine) Benzothiophenes (e.g.,S-DMT (1-thia-DMT),3-APBT (1-thia-AMT)) Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g.,HT,DMHT) I-32 IAL IN-399 Indazolethylamines (e.g.,AL-34662,AL-38022A,O-methyl-AL-34662,VU6067416,YM-348) Indenylethylamines (e.g.,C-DMT (1-carba-DMT)) Indolizinylethylamines (e.g.,TACT908 (2ZEDMA),1ZP2MA,1Z2MAP1O) Indolylaminopropanes (e.g.,1-API,2-API,4-API,5-API (5-IT; PAL-571),6-API (6-IT),7-API) Iprindole Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan,LY-334370,naratriptan) Ondansetron Oxazinopyridoindoles (e.g.,IHCH-8134) Phenethylamines (e.g.,phenethylamine,amphetamine) Piperidinylbenzimidazolines (e.g.,benperidol,timiperone) Piperazinylbenzisothiazoles (e.g.,lurasidone,perospirone,tiospirone,ziprasidone) Piperidinylbenzisoxazoles (e.g.,iloperidone,milsaperidone,ocaperidone,paliperidone,risperidone) Piperidinylindoles (e.g.,BRL-54443,LY-334370,naratriptan,sertindole,SN-22) Pirlindole Pyridinylbenzimidazoles (e.g.,droperidol) Pyridinylindoles (e.g.,tepirindole) Pyridopyrroloquinoxalines (e.g.,IHCH-7113,IHCH-7079,IHCH-7086,lumateperone,deulumateperone,ITI-1549) Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA),3-pyrrolylethylamine (3-NEA),3-pyrrolylpropylamine) Pyrrolopyridinylethylamines (e.g.,WAY-208466) Quinolinylethylamines (e.g.,mefloquine) Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088,LY-367265,RU-24,969) Tetrahydropyridinylpyrrolopyridines (e.g.,(R)-69 (3IQ),(R)-70,CP-93129,CP-94253) Tetrindole Tipindole Zilpaterol (RU-42173)
See also:Phenethylamines Ergolines and lysergamides Psychedelics Simple tryptamines and common derivatives

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