Chemistry:Metaescaline
Metaescaline (ME), also known as 3-ethoxy-4,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1] It is the analogue of mescaline in which the methoxy group at the 3 position has been replaced with an ethoxy group.[1] The drug is also the positional isomer of escaline in which the methoxy group at the 3 (meta) position and the ethoxy group at the 4 position have been interchanged.[1]
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists metaescaline's dose as 200 to 350 mg orally and its duration as 8 to 12 hours.[1] Its onset was described as slow and ranged from 0.5 to 1.5 hours.[1] The drug's potency is similar to that of mescaline.[1][2]
The effects of metaescaline were reported to include brightening of colors, mildly heightened visual awareness and quite heightened auditory awareness, no closed-eye imagery to significant closed-eye visuals, visual distortions such as walls dissolving, thinking changes, associative thinking, introspection, and insights.[1] Other effects included a "marvelous feeling inside", euphoria, feeling energetic, easy talking and talkativeness, relaxation, disinhibition, feeling connected and bonded with others, and subjective effects being more based in feelings than cognitive.[1] No hangover was reported.[1] It was said that no one was reluctant to repeat the experience.[1] Alcohol was reported to potentiate or rekindle the effects of metaescaline in a TOMSO-like manner in one report.[1]
Metaescaline was variously described as a "sterner mescaline" and as "not dramatic like some psychedelics".[1] Unlike mescaline or peyote, there was little body discomfort, no nausea, and only occasional hyperreflexia.[1] In addition, metaescaline was said to have less exaggeration of color perception than mescaline and that music was associated with little imagery in contrast to mescaline.[1] The transference characteristic of MDMA were said to be basically absent, but it was felt that metaescaline might nonetheless be useful for psychedelic-assisted psychotherapy purposes.[1]
Interactions
Chemistry
Synthesis
The chemical synthesis of metaescaline has been described.[1]
Analogues
Analogues of metaescaline include mescaline, escaline, metaproscaline, asymbescaline, symbescaline, and trisescaline (trescaline), among others.[1]
History
Metaescaline was mentioned in the literature by Abram Hoffer and Humphrey Osmond in their 1967 book The Hallucinogens.[3] It was subsequently described by Alexander Shulgin and Peyton Jacob III in 1984.[2] Following this, metaescaline was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
Legal status
Canada
Metaescaline is not a controlled substance in Canada as of 2025.[4]
United States
Metaescaline is not an explicitly controlled substance in the United States.[5] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption. In addition, it may be considered scheduled as a positional isomer of 3,4,5-trimethoxyamphetamine (TMA) and escaline.[5][6]
See also
- Scaline
- TWEETIO § Scalines
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 1.16 1.17 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. "Metaescaline entry". http://www.erowid.org/library/books_online/pihkal/pihkal119.shtml.
- ↑ 2.0 2.1 "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". Journal of Medicinal Chemistry 27 (7): 881–888. July 1984. doi:10.1021/jm00373a013. PMID 6737431.
- ↑ The Hallucinogens. Academic Press. 1967. ISBN 978-0-12-351850-7. https://books.google.com/books?id=5-NrAAAAMAAJ. Retrieved 29 November 2025.
- ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html.
- ↑ 5.0 5.1 Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf
- ↑ Drug Enforcement Administration (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances". https://www.federalregister.gov/documents/2007/12/03/E7-23413/definition-of-positional-isomer-as-it-pertains-to-the-control-of-schedule-i-controlled-substances.
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