Chemistry:3-Methoxy-4-ethoxyphenethylamine

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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]

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  MEPEA entry
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. "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." 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. "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." 
  4. ↑ 4.0 4.1 4.2 Otakar Leminger (1972). "Příspěvek k chemii v jádře alkoxylovaných β-fenoetylaminů – II: O některých v jádře alkoxylovaných β-fenoetylaminech, resp. jejich sulfátech". Chemický Průmysl 22: 553–557. https://isomerdesign.com/bitnest/external/ChemickyPrumysl/22.553. 



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