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]

Metaescaline

Clinical data
Other names	ME; 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
IUPAC name 2-(3-ethoxy-4,5-dimethoxyphenyl)ethan-1-amine
CAS Number	90132-31-3 Y
PubChem CID	44350068
ChemSpider	21106344 Y
UNII	M4HNS35MM2
ChEMBL	ChEMBL126963 Y
CompTox Dashboard (EPA)	DTXSID30658376
Chemical and physical data
Formula	C12H19NO3
Molar mass	225.288 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1c(cc(cc1OCC)CCN)OC
InChI 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
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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]

See also

• Substituted mescaline analogue
• TWEETIO § Scalines