Escaline

Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. https://erowid.org/library/books_online/pihkal/pihkal072.shtml It is the 4-ethoxy analogue of mescaline (3,4,5-trimethoxyphenethylamine) and the phenethylamine (non-α-methyl) analogue of 3C-E (3,5-dimethoxy-4-ethoxyamphetamine). The drug has been encountered as a novel designer drug.

Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists escaline's dose range as 40 to 60mg orally. The duration is stated to be 8 to 12hours, whereas the onset is not described. Escaline is approximately 5- to 8-fold more potent than mescaline.

The effects of escaline have been described relatively limitedly but have been reported to include sensory enhancement without an intellectual component, little synthesis of external sensory inputs like music or visual stimuli, easy fantasy, rational thinking and insight, pleasantness, powerful and complex intoxication, pain relief, muscle tension, motor incoordination to the extent of not being able to walk or tie one's shoelaces, body tension that outweighed the desired psychoactive effects, tachycardia, dehydration, nightmares, and next-day hangover symptoms such as tiredness and low energy.

Interactions

Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A >10,000 (Ki)372–724 ()23–40% () 5-HT1B >10,000 (Ki)513–1,410 ()62–98% () 5-HT1D 724 (Ki)117–2,690 ()56–100% () 5-HT1E >10,000 (Ki)4,370–7,590 ()73–113% () 5-HT1F (Ki)182–3,470 ()20–72% () 5-HT2A 216–>10,000 (Ki)107–2,140 ()62–108% () 5-HT2B 148–551 (Ki)257–708 ()53–105% () 5-HT2C 177–4,366 (Ki)741–2,450 ()68–112% () 5-HT3 >10,000 5-HT4 5-HT5A >10,000 5-HT6 >10,000 5-HT7 >10,000 α1A–α1D >10,000 α2A 2,450 α2B >10,000 α2C 4,790 β1–β3 >10,000 D1, D2 >10,000 D3 380 D4 525 (Ki)1,290–6,610 ()24–88% () D5 >10,000 H1–H4 >10,000 M1–M5 >10,000 TAAR1 I1 σ1, σ2 >10,000 >10,000 (Ki) () >10,000 (Ki) () >10,000 (Ki) () Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:

The comprehensive receptor interactions of escaline have been described. It acts as an agonist of the serotonin 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, and 5-HT2C receptors, among other actions. The drug is also an agonist of the dopamine D4 receptor, though not of any other dopamine receptors. Besides escaline, the receptor interactions of various escaline analogues and derivatives have been described.

Escaline produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents. It partially substitutes for LSD in rodent drug discrimination tests. The drug is unusual among serotonergic psychedelics in only partially rather than fully substituting for LSD.

Chemistry Synthesis The chemical synthesis of escaline has been described.

Analogues Analogues of escaline include mescaline, proscaline, allylescaline, methallylescaline, 3C-E, and 3-methoxy-4-ethoxyphenethylamine (MEPEA; 3-desmethoxyescaline), among others.

History Escaline was first described in the scientific literature by George S. Grace in 1934. Subsequently, it was also described by F. Benington and colleagues in 1954. It was later further described by Otakar Leminger in 1972. Then, it was studied by David E. Nichols and colleagues, who prepared a series of mescaline analogues that included escaline, proscaline, and isoproscaline and published their work in 1977.

Society and culture Legal status Canada Escaline is not a controlled substance in Canada as of 2025.

Sweden Escaline is illegal in Sweden as of 26 January 2016.

United States Escaline is a Schedule I controlled substance (DEA #7930) in the United States with the reason cited being that it is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA).

Escaline

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