Metaescaline

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Metaescaline
Metaescaline.svg
Clinical data
Other namesME; 3-Ethoxy-4,5-dimethoxyphenethylamine; 3,4-Dimethoxy-5-ethoxyphenethylamine
Routes of
administration 		Oral [1]
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action 0.5–1.5 hours [1]
Duration of action 8–12 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
Formula C12H19NO3
Molar mass 225.288 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 Yes check.svgY
  • Key:HNBAVLIQFTYMAX-UHFFFAOYSA-N Yes check.svgY
   (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]

Contents

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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 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. 1 2 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.
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