Methoxyphenethylamines (MPEAs), as well as methoxyamphetamines (MAs) in the case of the amphetamine (α-methylphenethylamine) homologues, are substituted phenethylamines with one or more methoxy groups. In some cases, one or more of the methoxy groups may also be extended to form other alkoxy and related groups such as ethoxy or propoxy. Methoxyphenethylamines may have additional substitutions as well.
Many methoxyphenethylamines that have multiple methoxy groups in the 2- through 5-positions of the phenyl ring, for instance mescaline, 2C-B, TMA, DOM, and 25I-NBOMe, are serotonin 5-HT2A receptor agonists and serotonergic psychedelics. Other methoxyphenethylamines, particularly monomethoxyamphetamines like para-methoxyamphetamine (PMA), are monoamine releasing agents of serotonin, norepinephrine, and/or dopamine, with stimulant and/or entactogen-related effects.
Compounds closely related to methoxyphenethylamines include methylenedioxyphenethylamines (MDxx) like MDA, MDMA, and MMDA, in which two adjacent methoxy groups are bridged, and FLY compounds like 2C-B-FLY, in which methoxy groups are cyclized into furan rings to create benzofuran ring systems.
Almost all known psychedelic phenethylamines are either methoxyphenethylamines or closely related compounds like MDxx or benzofurans. There are only a few known exceptions, such as fenfluramine and lorcaserin, which can both produce psychedelic effects at high and supratherapeutic doses. This is in notable contrast to tryptamines such as dimethyltryptamine (DMT), which require no specific ring substitutions to be psychedelic.
List of methoxyphenethylamines Phenethylamines
Monomethoxyphenethylamines (MPEAs) (e.g., 2-MPEA, 3-MPEA, 4-MPEA) Dimethoxyphenethylamines (DMPEAs) (e.g., 2,5-DMPEA (2C-H), 3,4-DMPEA, 3,5-DMPEA (DMPEA-6), MEPEA, macromerine) 2Cs (4-substituted 2,5-DMPEAs) (e.g., 2C-B, 2C-C, 2C-D, 2C-E, 2C-I, 2C-T-2) TWEETIOs (e.g., 2CB-2-EtO, 2CD-5-EtO, 2CT2-2-EtO, ASR-2001 (2CB-5PrO)) Scalines (4-substituted 3,5-DMPEAs) (e.g., 4-desoxymescaline (DESOXY; 4-Me-3,5-DMPEA)) Ψ-PEAs (4-substituted 2,6-DMPEAs) (e.g., Ψ-2C-T-4) Trimethoxyphenethylamines (TMPEAs) (e.g., 2,4,5-TMPEA (2C-O; TMPEA-2), mescaline (3,4,5-TMPEA; TMPEA-1), isomescaline (2,3,4-TMPEA; TMPEA-3), ψ-2C-O (2,4,6-TMPEA), 2,3,5-TMPEA (TMPEA-4), 2,3,6-TMPEA (TMPEA-5)) 2Cs (4-substituted 2,5-DMPEAs) (e.g., 2C-O, 2C-O-4, 2C-O-22) Scalines (4-substituted 3,5-DMPEAs) (e.g., mescaline, escaline, proscaline, allylescaline, methallylescaline) Ψ-PEAs (4-substituted 2,6-DMPEAs) (e.g., Ψ-2C-O (TMPEA-6), Ψ-2C-DFMO (ψ-2C-O-35)) Other substitution patterns (e.g., isomescaline, CT-5172) Tetramethoxyphenethylamines (TeMPEAs) (e.g., TeMPEA (2,3,4,5-TeMPEA), TeMPEA-2 (2,3,4,6-TeMPEA), TeMPEA-3 (2,3,5,6-TeMPEA))
Pentamethoxyphenethylamine (PeMPEA or 2,3,4,5,6-PeMPEA)
(N-(2-methoxybenzyl)phenethylamines or NBOMes) (e.g., 25-NBOMes, 25I-NBOMe, NBOMe-mescaline, 24-NBOMes, 24H-NBOMe)
PEA-NDEPAs (e.g., PEA-NM-NDEPA, 3,4-DMPEA-NDEPA, 25D-NM-NDEAOP (25D-NM-NDEPA), M-NDEPA)
Amphetamines
Monomethoxyamphetamines (MAs) (e.g., OMA (2-MA), MMA (3-MA), PMA (4-MA), 3-methoxy-4-methylamphetamine (MMA), 4-ETA, 2-TOM, 5-TOM, 2-TOET, 5-TOET, TOMSO) N-Alkyl-MAs (e.g., methoxyphenamine (OMMA), MMMA, PMMA, PMEA) Dimethoxyamphetamines (DMAs) (e.g., 2,4-DMA (DMA-3), 2,5-DMA (DMA-4; DOH), 3,4-DMA, 3,5-DMA (DMA-6), 3,4-DMMA, methoxamine (β-OH-2,6-DMA)) DOx (4-substituted 2,5-DMAs) (e.g., DOB, DOC, DOET, DOI, DOM, Aleph (DOT)) N-Alkyl-DOx (e.g., Beatrice (methyl-DOM; MDOM), N-methyl-DOET, methyl-DOB (MDOB), N-methyl-DOI, IDNNA (N,N-dimethyl-DOI), N-methyl-TMA-2) 3Cs (4-substituted 3,5-DMAs) (e.g., 4-Br-3,5-DMA, 4-PhPr-3,5-DMA) Ψ-PEAs (4-substituted 2,6-DMAs) (e.g., Ψ-DOM, Ψ-DODFMO, TMA-6 (Ψ-TMA-2; 2,4,6-TMA)) Trimethoxyamphetamines (TMAs) (e.g., TMA (3,4,5-TMA), TMA-2 (2,4,5-TMA), TMA-3 (2,3,4-TMA), TMA-4 (2,3,5-TMA), TMA-5 (2,3,6-TMA), TMA-6 (2,4,6-TMA; Ψ-TMA-2)) N-Alkyl-TMAs (e.g., N-methyl-TMA, N-methyl-TMA-2) DOx (4-substituted 2,5-DMAs) (e.g., TMA-2, MEM, MPM, MALM, MMALM, MTFEM) 3Cs (4-substituted 3,5-DMAs) (e.g., TMA (3C-M), 3C-E, 3C-P, 3C-AL, 3C-MAL, 3C-DFE, 3C-TFE, 3C-BZ) Ψ-PEAs (4-substituted 2,6-DMAs) (e.g., TMA-6 (Ψ-TMA-2)) Tetramethoxyamphetamines (TeMAs) (e.g., TeMA (2,3,4,5-TeMA), TeMA-2 (2,3,4,6-TeMA), TeMA-3 (2,3,5,6-TeMA)) Pentamethoxyamphetamine (PeMPA or 2,3,4,5,6-PeMPA) 25-NB or NBOMes (N-benzyl-MAs) (e.g., DOM-NBOMe, DOB-NBOMe, DOI-NBOMe) AMPH-NDEPAs (e.g., DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, TMA-2-NDEPA)
Phenylisobutylamines
4Cs (4-substituted 2,5-dimethoxyphenylisobutylamines) (e.g., Ariadne (4C-D), 4C-B, 4C-I, 4C-P, 4C-T-2, 4C-TFM) Others (e.g., α-ethylmescaline (AEM))
α-Propylphenethylamines
5Cs (4-substituted 2,5-dimethoxy-α-propylphenethylamines) (e.g., 5C-D) Others (e.g., α-propylmescaline (APM))
Others and related compounds Ring-extended phenethylamines
Methylenedioxyphenethylamines (MDxx) (e.g., MDPEA (homopiperonylamine), MDMPEA (homarylamine), MDA (tenamfetamine), MDMA (midomafetamine), MDEA, BDB (J), MBDB (methyl-J), BDP (K), MPAP (PBDP; propyl-K), methylone (MDMC)) Monomethoxymethylenedioxyphenethylamines (MMPEAs) (e.g., lophophine (MMDPEA; 2C-MMDA-1), 2C-MMDA-2 (MMDPEA-2; 2C-2), 2C-MMDA-3a (MMDPEA-3a; 2C-3a), 2C-MMDA-4, MMDA, MMDA-2, MMDA-3a, MMDA-3b, MMDA-4, MMDA-5, EMDA-2) Dimethoxymethylenedioxyphenethylamines (DMMPEAs) (e.g., 2C-DMMDA, 2C-DMMDA-2, DMMDA, DMMDA-2, DMMDA-3, DMMDA-4, DMMDA-5, DMMDA-6) Ethylenedioxyphenethylamines (EDxx) (e.g., EDA, EDMA, EDMC, MEDA) Benzofurans (e.g., 5-APB, 5-MAPB, 6-APB, 5-APDB, 6-APDB, F (F-1), F-2, F-22, DOH-5-hemiFLY (semi-fly), DOB-5-hemiFLY (bromo-semi-fly)) FLY compounds (benzodifurans) (e.g., 2C-B-FLY, DOB-FLY, Bromo-DragonFLY (DOB-DFLY), TFMFly) Methylenethiooxyphenethylamines (e.g., SDA (3T-MDA), SDMA (3T-MDMA), 4T-MMDA-2) Others (e.g., MTDA)
Rigid/constrained phenethylamines
Tetrahydroisoquinolines (THIQs) (e.g., anhalinine, pellotine, lophophorine, DOM-CR, DOB-CR) Phenylcyclopropylamines (e.g., DMCPA, TMT) 1-Aminomethylindanes (1-AMIs) (e.g., 2CB-Ind, AMMI, jimscaline, bromojimscaline) 2-Aminoindanes (2-AIs) (e.g., DOM-AI, MDAI, MDMAI, MEAI, MMAI) 2-Aminotetralins (2-ATs) (e.g., DOM-AT, MDAT, MDMAT) Benzocyclobutenes (BCBs) (e.g., 2CBCB-NBOMe, TCB-2 (2CBCB), tomscaline, bromotomscaline) 3-Phenylpiperidines (3PIPs) (e.g., LPH-5, LPH-48, 2C-B-3PIP, 2C-B-3PIP-NBOMe, 2C-B-3PIP-POMe, DEMPDHPCA-2C-D) 2-Benzylpiperidines (e.g., DMBMPP (juncosamine)) Phenylalkylpyrrolidines (e.g., MOPPP, MOPVP, MDPPP, MDPBP, MDPV, MDPHP, MDPEP) Others (e.g., 2C-B-aminorex (2C-B-AR), 2C-B-morpholine (2C-B-MOR), 2C-B-PYR, 2C-B-5-hemiFLY-α6 (BNAP), 2CB7 (2C-B-5-hemiFLY-β7), 2CBecca, 2CJP, 2CLisaB, 2CLisaH, CT-5126, TFMBOX, ZC-B)
Other psychedelic phenethylamines There are few known psychedelic phenethylamines that are not methoxyphenethylamines or related compounds like methylenedioxyphenethylamines or benzofurans. Those that are known include the 3-trifluoromethyl phenethylamine fenfluramine, the cyclized phenethylamine lorcaserin, and the benzothiophenes 5-APBT and 6-APBT. Certain other phenethylamines, like naphthylaminopropane (NAP; PAL-287), are also known to act as serotonin 5-HT2A receptor agonists, but have not been assessed in terms of psychedelic-type effects in animals or humans. 4-Fluoroamphetamine (4-FA) has been described as producing a very mild "psychedelic" state, intermediate between that of amphetamine and MDMA, although it is unclear whether this is related to induction of monoamine release or serotonin 5-HT2A receptor agonism.
Compounds by substituents and substitution patterns
See also Substituted phenethylamine PiHKAL: A Chemical Love Story (1991) The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (2011)
References