Substituted methoxyphenethylamine

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.^[1][2][3] 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.^[1][2] Methoxyphenethylamines may have additional substitutions as well.^[1][2][3]

Mescaline (3,4,5-TMPEA), an example of a major methoxyphenethylamine.

MMDA, an example of a methylenedioxyphenethylamine.

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-HT_2A receptor agonists and serotonergic psychedelics.^[1][2][3] 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.^[1][2]

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.^[1][2][3]

Almost all known psychedelic phenethylamines are either methoxyphenethylamines or closely related compounds like MDxx or benzofurans.^[1][2] There are only a few known exceptions, such as fenfluramine^[4] and lorcaserin, which can both produce psychedelic effects at high and supratherapeutic doses.^[1][2][5] This is in notable contrast to substituted tryptamines such as DET, which require no specific ring substitutions to be psychedelic.^[6][7]

List of methoxyphenethylamines

Phenethylamines

See also: Substituted phenethylamine

• 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., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CT2-5-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 (TMPEA-2; 2C-O), mescaline (3,4,5-TMPEA), isomescaline (2,3,4-TMPEA))
  • 2Cs (4-substituted 2,5-DMPEAs) (e.g., 2C-O, 2C-O-2, 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)
• 25-NB or NBOMes (N-benzyl-MPEAs) (e.g., 25I-NBOMe, NBOMe-mescaline)
• PEA-NDEPAs (e.g., 3,4-DMPEA-NDEPA, 25D-NM-NDEAOP (25D-NM-NDEPA), M-NDEPA)

Amphetamines

See also: Substituted amphetamine

• 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))
  • 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)
• 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))
  • 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-E, 3C-P, 3C-IP, 3C-AL, 3C-MAL, 3C-FE)
  • Ψ-PEAs (4-substituted 2,6-DMAs) (e.g., TMA-6 (Ψ-TMA-2), Ψ-DODFMO)
• 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

See also: Substituted phenylisobutylamine

• 4Cs (4-substituted 2,5-dimethoxyphenylisobutylamines) (e.g., Ariadne (4C-D), 4C-B, 4C-C, 4C-E, 4C-I, 4C-T-2)
• Others (e.g., α-ethylmescaline)

α-Propylphenethylamines

See also: Substituted α-propylphenethylamine

• 5Cs (4-substituted 2,5-dimethoxy-α-propylphenethylamines) (e.g., 5C-D)
• Others (e.g., α-propylmescaline)

Others and related compounds

Ring-extended phenethylamines

See also: Substituted methylenedioxyphenethylamine and Substituted benzofuran

• Methylenedioxyphenethylamines (MDxx) (e.g., MDPEA, MDMPEA, MDA, MDMA, MDEA, BDB (J), MBDB (methyl-J), BDP (K), MPAP (propyl-K), methylone (MDMC))
  • Monomethoxymethylenedioxyphenethylamines (MMPEAs) (e.g., lophophine (MMDPEA; 2C-MMDA-1), 2C-MMDA-2 (MMDPEA-2), 2C-MMDA-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)
• Benzofurans and FLY compounds (e.g., 5-APB, 6-APB, 5-APDB, 6-APDB, 2C-B-FLY, DOB-FLY, Bromo-DragonFLY, TFMFly, F, F-2, F-22)

Rigid/constrained phenethylamines

See also: Cyclized phenethylamine

• Tetrahydroisoquinolines (e.g., anhalinine, pellotine, lophophorine, DOM-CR, DOB-CR)
• Phenylcyclopropylamines (e.g., DMCPA, TMT)
• 1-Aminomethylindanes (1-AMIs) (e.g., 2CB-Ind, AMMI, jimscaline)
• 2-Aminoindanes (2-AIs) (e.g., DOM-AI, MDAI, MDMAI, MEAI, MMAI)
• 2-Aminotetralins (2-ATs) (e.g., DOM-AT, MDAT, MDMAT)
• Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline)
• 3-Phenylpiperidines (e.g., LPH-5, LPH-48, DEMPDHPCA-2C-D)
• Others (e.g., 2C-B-aminorex, 2C-B-morpholine, 2C-B-PYR, 2C-B-5-hemiFLY-α6, 2CBecca, 2CJP, 2CLisaB, 2CLisaH, CT-5126, DMBMPP (juncosamine), TFMBOX, ZC-B)

Other psychedelic phenethylamines

There are few known psychedelic phenethylamines that are not methoxyphenethylamines or related compounds like methylenedioxyphenethylamines or benzofurans.^[1][2] Those that are known include the 3-trifluoromethyl phenethylamine fenfluramine,^[4][8][9] the rigid 4-chloro phenethylamine lorcaserin,^[5] and the benzothiophenes 5-APBT and 6-APBT.^[1][2][10] Certain other phenethylamines, like naphthylaminopropane (NAP; PAL-287), are also known to act as serotonin 5-HT_2A receptor agonists, but have not been assessed in terms of psychedelic-type effects in animals or humans.^[11][12] 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-HT_2A receptor agonism.^[13]

Compounds by substituents and substitution patterns

• v
• t
• e

Substituted methoxyphenethylamine extended at the 4 position

Substituent	No ether (4-)				4-Ether (4-O-)				4-Thioether (4-S-)
	2C	DOx	Scaline	3C	2C-O-x	DOO-x	Scaline-O-x	3C-O-x	2C-T-x	DOT-x	Scaline-T-x	3C-T-x
H	2C-H	2,5-DMA	3,5-DMPEA	3,5-DMA	–	DOOH	DESMETHYL	α-Me-DES…	2C-T-0	–	–	–
Methyl	2C-D	DOM	DESOXY	4-Me-3,5-DOM	2C-O	TMA-2	Mescaline	TMA	2C-T	Aleph	4-Thiomescaline	α-Me-4-TM
Ethyl	2C-E	DOET	DE	4,3,5-DOET	2C-O-2	MEM	Escaline	3C-E	2C-T-2	Aleph-2	4-Thioescaline	–
Methallyl	2C-1MV	–	–	–	2C-O-3	MMALM	Methallylescaline	3C-MAL	2C-T-3	Aleph-3	–	–
Isopropyl	2C-IP	DOiP	DIP	–	2C-O-4	MIPM	Isoproscaline	3C-IP	2C-T-4	Aleph-4	–	–
Cyclohexyl	–	–	–	–	–	–	–	–	2C-T-5	Aleph-5	–	–
Phenyl	2C-Ph	–	Biscaline	–	–	–	Phescaline	–	2C-T-6	Aleph-6	–	–
Propyl	2C-P	DOPR	DPR	4,3,5-DOPR	2C-O-7	MPM	Proscaline	3C-P	2C-T-7	Aleph-7	4-Thioproscaline	–
Cyclopropylmethyl	–	DOCPM	–	–	–	–	Cyclopropylmescaline	3C-CPM	2C-T-8	Aleph-8	–	–
tert-Butyl	2C-tBu	DOTB	–	–	–	–	–	–	2C-T-9	–	–	–
Pyridin-2-yl	–	–	–	–	–	–	–	–	2C-T-10	–	–	–
4-Bromophenyl	–	–	–	–	–	–	–	–	2C-T-11	–	–	–
Morpholin-4-yl	2C-MOR	–	–	–	–	–	–	–	2C-T-12	–	–	–
2-Methoxyethyl	–	DOMeOEt	–	–	–	–	4-Methoxyescaline	–	2C-T-13	–	–	–
2-Methylthioethyl	–	DOMeSEt	–	–	–	–	4-Methylthioescaline	–	2C-T-14	–	–	–
Cyclopropyl	2C-CP	–	–	–	–	–	Cycloproscaline	–	2C-T-15	–	–	–
Allyl	2C-AL	–	DAL	–	2C-O-16	MALM	Allylescaline	3C-AL	2C-T-16	Aleph-16	–	–
sec-Butyl	2C-sBu	DOSB	–	–	–	–	sec-Buscaline	–	2C-T-17	–	–	–
Cyclobutyl	2C-CB	–	–	–	–	–	–	–	2C-T-18	–	–	–
Butyl	2C-Bu	DOBU	–	–	2C-O-19	MBM	Buscaline	3C-B	2C-T-19	Aleph-19	4-Thiobuscaline	α-Me-4-TB
2-Fluoroethyl	2C-EF	DOEF	–	–	2C-O-21	MFEM	2-Fluoroescaline	3C-FE	2C-T-21	Aleph-21	–	–
2,2-Difluoroethyl	2C-DFE	–	–	–	2C-O-21.5	MDFEM	2,2-Difluoroescaline	3C-DFE	2C-T-21.5	–	–	–
2,2,2-Trifluoroethyl	2C-TFE	DOTFE	DTFE	–	2C-O-22	MTFEM	3,3,3-Trifluoroescaline	3C-TFE	2C-T-22	–	–	–
Cyclopentyl	2C-CPe	–	–	–	–	–	Cyclopentscaline	–	2C-T-23	–	–	–
Diethylamino	–	–	–	–	–	–	–	–	2C-T-24	–	–	–
Isobutyl	2C-iBu	DOIB	–	–	–	–	Isobuscaline	3C-IB	2C-T-25	–	–	–
1,3-Difluoroisopropyl	–	–	–	–	–	–	1,3-Difluoroisoprosc…	–	2C-T-26	–	–	–
Benzyl	2C-BN	DOBz	–	–	2C-O-27	MBZM	Benzscaline	3C-BZ	2C-T-27	–	–	–
3-Fluoropropyl	2C-FP	DOPF	–	–	2C-O-FP	–	3-Fluoroproscaline	3C-FP	2C-T-28	–	–	–
Propargyl	2C-YNP	–	–	–	–	–	PROPYNYL	–	2C-T-29	–	–	–
4-Fluorobutyl	–	–	–	–	–	–	–	–	2C-T-30	–	4F-TB	–
4-Trifluoromethylbenzyl	–	–	–	–	–	–	–	–	2C-T-31	–	–	–
Pentafluorobenzyl	–	–	–	–	–	–	–	–	2C-T-32	–	–	–
3-Methoxybenzyl	2C-MBM	DO3MeOBZ	–	–	–	–	–	–	2C-T-33	–	–	–
Fluoromethyl	2C-FM	DOFM	–	–	–	DOFMO	Fluoromescaline	–	2C-T-34	–	–	–
Difluoromethyl	2C-DFM	DODFM	–	–	–	DODFMO	Difluoromescaline	3C-DFM	2C-T-35	–	–	–
Trifluoromethyl	2C-TFM	DOTFM	DTFM	–	2C-O-TFM	DOTFMO	Trifluoromescaline	–	2C-T-36	Aleph-TFM	4-TM-TFM	–
Amyl	2C-AM	DOAM	±	±	–	MAM	Amylescaline	3C-A	±	Aleph-S-amyl	TA	–
Hexyl	2C-Hx	DOHx	–	–	–	–	Hexylescaline	3C-H	–	–	–	–
Ethenyl	2C-V	DOV	DV	–	–	–	Viscaline	–	–	–	–	–
Ethynyl	2C-YN	DOYN	DYN	–	–	–	–	–	–	–	–	–
Methoxymethyl	2C-MOM	DOMOM	4-MeOMe…	–	–	–	4-Methoxymescaline	–	–	–	–	–
Ethoxymethyl	2C-EOM	DOMOE	–	–	–	–	–	–	–	–	–	–
4-Methoxyphenyl	2C-BI-8	–	–	–	–	–	–	–	–	–	–	–
Phenylethyl	2C-PhEt	DOPhEt	–	–	–	–	Phenescaline	–	–	Aleph-S-PhEt	–	–
3-Phenylpropyl	2C-PhPr	DOPP	–	4-PhPr-3,5-DMA	–	–	–	–	–	–	–	–
Notes: (1) The "2C-X-20" row is absent because "2C-X-3" and "2C-X-20" are synonyms/the same compounds. (2) Missing compounds can be found at Isomer Design.

See also

• PiHKAL: A Chemical Love Story (1991)
• The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (2011)