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5-MeO-MPMI

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

5-MeO-MPMI
Clinical data

Other names	5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine; CP-108509; CP108509
Drug class	Serotonergic psychedelic;Hallucinogen
ATC code	None
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name 5-methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
CAS Number	143321-57-7^Y
PubChemCID	9881324
ChemSpider	8057000^Y
UNII	N29TFW7VRV
ChEMBL	ChEMBL137485^Y
CompTox Dashboard(EPA)	DTXSID401027538
Chemical and physical data
Formula	C₁₅H₂₀N₂O
Molar mass	244.338 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CCC[C@@H]1CC2=CNC3=C2C=C(C=C3)OC
InChI InChI=1S/C15H20N2O/c1-17-7-3-4-12(17)8-11-10-16-15-6-5-13(18-2)9-14(11)15/h5-6,9-10,12,16H,3-4,7-8H2,1-2H3/t12-/m1/s1^Y Key:MKEGUJPBCIXABO-GFCCVEGCSA-N^Y
^NY (what is this?) (verify)

5-MeO-MPMI (developmental code nameCP-108509), also known as5-methoxy-N-methyl-(α,N-trimethylene)tryptamine, is apsychedelic drug of thepyrrolidinylmethylindole andcyclized tryptamine families.^[1]

Interactions

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Pharmacology

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Pharmacodynamics

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5-MeO-MPMI producespsychedelic-appropriate responding inanimal tests, with similarpotency toDOI.^[1] It has twoenantiomers, with only the (R)-enantiomer being active.^[1]

Chemistry

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Analogues

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Analogues of 5-MeO-MPMI includeMPMI,4-HO-MPMI,5-fluoro-MPMI,5-MeO-pyr-T,CP-122288,CP-135807, andeletriptan, among others.

History

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5-MeO-MPMI was first developed by the team led by J. E. Macor and colleagues in 1992.^[2] It was subsequently investigated by the team led byDavid E. Nichols fromPurdue University in the late 1990s.^[1]

References

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^^a ^b ^c ^dGerasimov M, Marona-Lewicka D, Kurrasch-Orbaugh DM, Qandil AM, Nichols DE (1999). "Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain".Journal of Medicinal Chemistry.42 (20):4257–4263.CiteSeerX 10.1.1.690.4941.doi:10.1021/jm990325u.PMID 10514296.
^Macor JE, Blake J, Fox CB, Johnson C,Koe BK, Lebel LA, Morrone JM, Ryan K, Schmidt AW, Schulz DW, et al. (1992). "Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin".Journal of Medicinal Chemistry.35 (23):4503–4505.doi:10.1021/jm00101a032.PMID 1447752.

External links

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5-MeO-MPMI - Isomer Design

Psychedelics

Tryptamines

No ring subs.	CYB004 (deuDMT) DALT DBT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT MET MiPT MPT NBoc-DMT NMT PALT PiPT 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-T 4-HO-TMT 4-HO-5-MeO-DMT 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-Acetoxytryptamines:4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MALT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT Luvesilocin (4-GO-DiPT; RE-104, FT-104)
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines: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-NiPT 5-MeO-NMT ASR-3001 (5-MeO-iPALT)
Other ring subs.	2,N,N-TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N,N-TMT 7,N,N-TMT 5-MeO-2,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) Bretisilocin (GM-2505; 5-fluoro-MET)
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) β-Carbolines andHarmala alkaloids (e.g.,harmine,harmaline,6-methoxyharmalan) Iboga alkaloids (e.g.,18-MAC,18-MC,coronaridine,ibogaine,ibogamine,ME-18-MC,noribogaine,tabernanthine,voacangine) Ibogalogs (e.g.,ibogainalog) 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) Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI),NEtPhOH-THPI)
Bioisosteres	Benzofurans (e.g.,5-MeO-DiBF,dimemebfe (5-MeO-BFE),mebfap) Benzothiophenes (e.g.,3-APBT) 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 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline N,N-Diformylmescaline Escaline Fluoroescaline Fluoroproscaline N-Formylmescaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline Methallylescaline N-Methylmescaline (M-M) NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-Bn 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-NH2 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-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x:2C-O 2C-O-2 2C-O-4 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,BOH-2C-B) HOT-x (e.g.,HOT-2,HOT-7,HOT-17) N-Ethyl-2C-B TWEETIOs (e.g.,2CD-2-ETO,2CD-5-ETO,2CE-5-ETO,2CE-5iPrO,2CT2-5-ETO,ASR-2001 (2CB-5PrO))
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) N-Hydroxy-DOM
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
Ψ-PEA	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 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 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly
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 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others:25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027
Others	2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM 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) TMAs (e.g.,TMA-3,TMA-4,TMA-5) TOMSO ZDCM-04 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

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)

Other ring system-substituted lysergamides:12-Hydroxy-LSD
12-Methoxy-LSD

Bioisosteres:JRT

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

Cyclized tryptamines:Banisteriopsis caapi (yagé)
Peganum harmala (Syrian rue)
Silene undulata
Tabernanthe iboga (iboga)

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-T 2-HO-NMT 2-Methyl-DET 2,N,N-TMT (2-Me-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 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-T 6,7-DHT 7-Chloro-T 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) Lespedamine (1-MeO-DMT) L-694247 MBT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T) N-DEAOP-NET N-DEAOP-NMT NAT NBoc-DMT NET/NETP NHT NiPT NMT NsBT NtBT PALT 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-EPT 4-AcO-MALT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 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-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 4,5-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 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-NiPT 5-HO-DPT 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-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O-methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 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) Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) 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
Cyclized tryptamines	5-MeO-IsoqT Barettin 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) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5F-MPMI,5-MeO-MPMI,CP-122288,CP-135807,eletriptan) Tetrahydrocarbazolamines (e.g.,ciclindole,flucindole,frovatriptan,LY-344864,ramatroban) Tetrahydropyridinylindoles (e.g.,RS134-49,RU-28253,NEtPhOH-THPI) Tetrahydropyrroloquinolines (e.g.,bufothionine,O-methylnordehydrobufotenine) 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,5-MeO-DiBF,BPAP,3-F-BPAP,dimemebfe,mebfap,oxa-noribogaine) Benzothiophenes (e.g.,3-APBT) 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) 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-94253) Tetrindole Tipindole Zilpaterol (RU-42173)
See also:Phenethylamines Ergolines and lysergamides Psychedelics