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    Escaline molecular structure

    Escaline Stats & Data

    E
    NPS DataHub
    MW225.29
    FormulaC12H19NO3
    CAS39201-82-6
    IUPAC2-(4-Ethoxy-3,5-dimethoxy-phenyl)-ethylamine
    SMILESNCCc1cc(OC)c(OCC)c(OC)c1
    InChIKeyRHOGRSKNWDNCDN-UHFFFAOYSA-N
    Phenethylamines; 2020/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2021/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2022/1. Von 2-Phenethylamin abgeleitete Verbindungen
    Chemical Class Phenethylamine
    Psychoactive Class Psychedelic

    Receptor Profile

    Receptor Actions

    Agonists
    5-HT2A receptor partial agonist (5-8 times greater affinity than mescaline)
    5-HT2C receptor agonist

    History & Culture

    Escaline was first described in the scientific literature by George S. Grace in 1934. It was subsequently synthesized and reported by F. Benington and colleagues in 1954. The compound was later re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues including escaline, proscaline, and isoproscaline, publishing their findings in 1977. The effects of escaline in humans were documented by Alexander Shulgin in his 1991 book PiHKAL: A Chemical Love Story. The name "escaline" derives from an etymological play on words related to its chemical structure. The central oxygen of mescaline bears a methyl group (one carbon), with the prefix "methyl" stemming from the Greek word "methy" meaning wine. When this methyl group is replaced with an ethyl group (two carbons), the natural linguistic extension transforms "mescaline" to "escaline." While this relationship is etymologically appealing, it carries no botanical significance—escaline has no known natural source. The coincidence that mescaline, methyl, and methoxy all begin with the letter "M" is simply fortuitous.

    Effect Profile

    Curated + 2 Reports
    Psychedelic 8.8

    Strong visuals, headspace, auditory effects, and body load

    Visual Intensity×3
    10
    Headspace Depth×3
    10
    Auditory Effects×1
    10
    Body Load / Somatic Effects×1
    10

    Community Effects

    TripSit
    Negative
    body load

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1h Half tolerance 10d Baseline ~14d

    Experience Report Analysis

    Erowid
    2 Reports
    2017–2017 Date Range
    1 With Age Data

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Real-World Dose Distribution

    62K Doses

    From 7 individual dose entries

    Oral (n=6)

    Median: 60.0mg 25th: 52.5mg 75th: 90.0mg 90th: 100.0mg
    mg/kg median: 0.76 mg/kg 75th: 1.05

    Legal Status

    Country Status Notes
    Germany Controlled (NpSG) Regulated under the Neue-psychoaktive-Stoffe-Gesetz (New Psychoactive Substances Act) since November 26, 2016. Production and importation with intent to distribute, administration to others, marketing, and trading are criminal offenses. Possession is prohibited but not subject to criminal penalty, though ordering the substance may constitute incitement to distribute.
    Japan Controlled substance Designated as a controlled substance under Japanese drug laws effective December 21, 2016.
    Switzerland Controlled (Verzeichnis E) Specifically listed by name in Verzeichnis E (Schedule E) of the Swiss controlled substances regulations.
    United Kingdom Illegal (Psychoactive Substances Act) Production, supply, and importation are prohibited under the Psychoactive Substances Act 2016, which took effect on May 26, 2016. This blanket legislation covers psychoactive substances not specifically exempted.
    United States Unscheduled Not specifically scheduled at the federal level. However, prosecution under the Federal Analogue Act remains possible if the substance is sold or possessed with intent for human consumption, given its structural similarity to the Schedule I substance mescaline.
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