Metaescaline

Metaescaline
Clinical data
Other namesME; 3-Ethoxy-4,5-dimethoxyphenethylamine; 3,4-Dimethoxy-5-ethoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action0.5–1.5 hours[1]
Duration of action8–12 hours[1]
Identifiers
  • 2-(3-ethoxy-4,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
  • COc1c(cc(cc1OCC)CCN)OC
  • InChI=1S/C12H19NO3/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3 Y
  • Key:HNBAVLIQFTYMAX-UHFFFAOYSA-N Y
  (verify)

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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

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

References

  1. ^ a b c d e f g h i j k l m n o p q r s t u Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "Metaescaline entry".
  2. ^ a b Jacob P, Shulgin AT (July 1984). "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". Journal of Medicinal Chemistry. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID 6737431.
  3. ^ Hoffer A, Osmond H (1967). The Hallucinogens. Academic Press. ISBN 978-0-12-351850-7. Retrieved 29 November 2025.
  4. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  5. ^ a b Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  6. ^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.
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