3-Methoxy-4-ethoxyphenethylamine

MEPEA
Clinical data
Other names	MEPEA; 3-Desmethoxyescaline
Routes of; administration	Oral
Drug class	Psychoactive drug
ATC code	None;
Pharmacokinetic data
Onset of action	≤1 hour
Duration of action	"Short"
Identifiers
	IUPAC name 2-(4-ethoxy-3-methoxyphenyl)ethan-1-amine;
CAS Number	36377-59-0 ;
PubChem CID	142076;
ChemSpider	125332 ;
UNII	P4MS942R6J;
CompTox Dashboard (EPA)	DTXSID40189904 ;
ECHA InfoCard	100.199.597
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(ccc1OCC)CCN;
	InChI InChI=1S/C11H17NO2/c1-3-14-10-5-4-9(6-7-12)8-11(10)13-2/h4-5,8H,3,6-7,12H2,1-2H3 ; Key:AFMUTJRFLRYILG-UHFFFAOYSA-N ;
	(what is this?) (verify)

MEPEA, also known as 3-methoxy-4-ethoxyphenethylamine or as 3-desmethoxyescaline, is a psychoactive drug of the phenethylamine family related to the psychedelic drug mescaline.^[1]^[2]^[3] It is the analogue of escaline in which the methoxy group at the 5 position has been removed.^[1]^[2]^[3]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists MEPEA's dose as 300 mg or more orally and its duration as "short".^[1]^[2]^[3] An earlier author listed its dose as 100 to 300 mg orally.^[1]^[4]

The effects of MEPEA have been reported to include very slight lightness, no body awareness, gentle lifting of spirits or mood enhancement, and no psychedelic effects, sensory enhancement, or other related changes.^[1]^[4] Its effects were described as "very quiet, very pleasant, and very light", with it producing a "plus-one" rating on the Shulgin Rating Scale in one report.^[1] In other publications, Shulgin said that MEPEA has little if any activity.^[2]^[3] The drug is one of the only known phenethylamines with only two substituents on the phenyl ring to show even a hint of central activity.^[1]

Chemistry

Synthesis

The chemical synthesis of MEPEA has been described.^[1]

Analogues

A couple of closely related compounds include 3-methoxy-4-allyloxyphenethylamine (MAPEA; 3-desmethoxyallylescaline) and 3-methoxy-4-propoxyamphetamine (POMA; 3-desmethoxyproscaline).^[1]

History

MEPEA was first described in the scientific literature by Otakar Leminger in 1972.^[1]^[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991 as well as in later publications.^[1]^[2]^[3]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. MEPEA entry
^ ^a ^b ^c ^d ^e Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025. There have been reports of mescaline analogs with a methoxy group removed. The analog 3,4-dimethoxyphenethylamine (DMPEA) has achieved some notoriety with the report of the observation of a pink spot in the thin-layer chromatographic analysis of the extracts of the urine of schizophrenic patients. The association of the spot with the diagnosis of schizophrenia has remained controversial, but the chemical identity has been shown to be DMPEA. Efforts to evoke some central nervous system (CNS) disturbance with this compound (orally, to > 1.5 grams (g); intravenously [IV], to > 10 mg) have produced no effects. Because of its close structural resemblance to the neurotransmitter dopamine (DA) (3,4-dihydroxyphenethylamine), this result has been disappointing. The 4-ethoxy homolog, 3-methoxy-4-ethoxyphenethylamine (2,3,4-trimethoxyphenethylamine) (MEPEA) has been assayed to 300 mg but has little if any activity.
^ ^a ^b ^c ^d ^e Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. The answer came from the direct assay of the [3,4-dimethoxyphenethylamine (3,4-DMPEA)] in humans as a possible psychoactive agent; it is not active. Neither is the 3,4-methylenedioxyphenethylamine counterpart, MDPEA, at least at dosages of up to 300mg orally. The 4-ethoxy homologue of DMPEA (MEРЕА) has been assayed to 300mg orally, and it also has little if any psychopharmacological activity.
^ ^a ^b ^c Otakar Leminger (1972). "Příspěvek k chemii v jádře alkoxylovaných β-fenoetylaminů – II: O některých v jádře alkoxylovaných β-fenoetylaminech, resp. jejich sulfátech" [A Contribution to the chemistry of alkoxylated phenethylamines – part 2: On some core-alkoxylated β-phenethylamines and their sulfates]. Chemický Průmysl. 22: 553–557. Archived from the original on 17 February 2026.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. MEPEA entry

[JacobShulgin1994-2] Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025. There have been reports of mescaline analogs with a methoxy group removed. The analog 3,4-dimethoxyphenethylamine (DMPEA) has achieved some notoriety with the report of the observation of a pink spot in the thin-layer chromatographic analysis of the extracts of the urine of schizophrenic patients. The association of the spot with the diagnosis of schizophrenia has remained controversial, but the chemical identity has been shown to be DMPEA. Efforts to evoke some central nervous system (CNS) disturbance with this compound (orally, to > 1.5 grams (g); intravenously [IV], to > 10 mg) have produced no effects. Because of its close structural resemblance to the neurotransmitter dopamine (DA) (3,4-dihydroxyphenethylamine), this result has been disappointing. The 4-ethoxy homolog, 3-methoxy-4-ethoxyphenethylamine (2,3,4-trimethoxyphenethylamine) (MEPEA) has been assayed to 300 mg but has little if any activity.

[Shulgin2003-3] Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. The answer came from the direct assay of the [3,4-dimethoxyphenethylamine (3,4-DMPEA)] in humans as a possible psychoactive agent; it is not active. Neither is the 3,4-methylenedioxyphenethylamine counterpart, MDPEA, at least at dosages of up to 300mg orally. The 4-ethoxy homologue of DMPEA (MEРЕА) has been assayed to 300mg orally, and it also has little if any psychopharmacological activity.

[Leminger1972-4] Otakar Leminger (1972). "Příspěvek k chemii v jádře alkoxylovaných β-fenoetylaminů – II: O některých v jádře alkoxylovaných β-fenoetylaminech, resp. jejich sulfátech" [A Contribution to the chemistry of alkoxylated phenethylamines – part 2: On some core-alkoxylated β-phenethylamines and their sulfates]. Chemický Průmysl. 22: 553–557. Archived from the original on 17 February 2026.

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