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Metaescaline

From Wikipedia, the free encyclopedia

Pharmaceutical compound
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
PubChemCID
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 checkY
  • Key:HNBAVLIQFTYMAX-UHFFFAOYSA-N checkY
  (verify)

Metaescaline (ME), also known as3-ethoxy-4,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine andscaline families related tomescaline.[1] It is theanalogue of mescaline in which themethoxy group at the 3 position has been replaced with anethoxy group.[1] The drug is also thepositional isomer ofescaline 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

[edit]

In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists metaescaline's dose as 200 to 350 mgorally and itsduration as 8 to 12 hours.[1] Itsonset was described as slow and ranged from 0.5 to 1.5 hours.[1] The drug'spotency is similar to that ofmescaline.[1][2]

The effects of metaescaline were reported to include brightening of colors, mildly heightenedvisual awareness and quite heightenedauditory awareness, noclosed-eyeimagery to significant closed-eye visuals,visual distortions such as walls dissolving, thinking changes, associative thinking,introspection, andinsights.[1] Other effects included a "marvelous feeling inside",euphoria, feelingenergetic, easy talking andtalkativeness,relaxation,disinhibition, feeling connected and bonded with others, and subjective effects being more based in feelings than cognitive.[1] Nohangover 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 aTOMSO-like manner in one report.[1]

Metaescaline was variously described as a "sterner mescaline" and as "not dramatic like some psychedelics".[1] Unlike mescaline orpeyote, there was littlebody discomfort, nonausea, and only occasionalhyperreflexia.[1] In addition, metaescaline was said to have less exaggeration of color perception than mescaline and thatmusic was associated with little imagery in contrast to mescaline.[1] Thetransference characteristic ofMDMA were said to be basically absent, but it was felt that metaescaline might nonetheless be useful forpsychedelic-assisted psychotherapy purposes.[1]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Chemistry

[edit]

Synthesis

[edit]

Thechemical synthesis of metaescaline has been described.[1]

Analogues

[edit]

Analogues of metaescaline includemescaline,escaline,metaproscaline,asymbescaline,symbescaline, andtrisescaline (trescaline), among others.[1]

History

[edit]

Metaescaline was mentioned in the literature byAbram Hoffer andHumphrey Osmond in their 1967 bookThe Hallucinogens.[3] It was subsequently described byAlexander Shulgin andPeyton Jacob III in 1984.[2] Following this, metaescaline was described in greater detail by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[1]

Society and culture

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Legal status

[edit]

Canada

[edit]

Metaescaline is not acontrolled substance inCanada as of 2025.[4]

United States

[edit]

Metaescaline is not an explicitlycontrolled substance in theUnited States.[5] However, it could be considered a controlled substance under theFederal Analogue Act if intended for human consumption. In addition, it may be considered scheduled as apositional isomer of3,4,5-trimethoxyamphetamine (TMA) andescaline.[5][6]

See also

[edit]

References

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  1. ^abcdefghijklmnopqrstuShulgin A,Shulgin A (September 1991).PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press.ISBN 0-9630096-0-5.OCLC 25627628."Metaescaline entry".
  2. ^abJacob 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. Retrieved29 November 2025.
  4. ^"Controlled Drugs and Substances Act".Department of Justice Canada. Retrieved19 January 2026.
  5. ^abOrange 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.

External links

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