Escaline
Psychedelic phenthylamine drug
From Wikipedia, the free encyclopedia
Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1] 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).[1] The drug has been encountered as a novel designer drug.[2]
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| Other names | E; 3,5-Dimethoxy-4-ethoxyphenethylamine; 4-Ethoxy-3,5-dimethoxyphenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Duration of action | 8–12 hours[1] |
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| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
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| Melting point | 165 to 166 °C (329 to 331 °F) (hydrochloride) |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists escaline's dose range as 40 to 60 mg orally.[1][3] The duration is stated to be 8 to 12 hours, whereas the onset is not described.[1] Escaline is approximately 5- to 8-fold more potent than mescaline.[4]
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.[1]
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | >10,000 (Ki) 372–724 (EC50) 23–40% (Emax) |
| 5-HT1B | >10,000 (Ki) 513–1,410 (EC50) 62–98% (Emax) |
| 5-HT1D | 724 (Ki) 117–2,690 (EC50) 56–100% (Emax) |
| 5-HT1E | >10,000 (Ki) 4,370–7,590 (EC50) 73–113% (Emax) |
| 5-HT1F | ND (Ki) 182–3,470 (EC50) 20–72% (Emax) |
| 5-HT2A | 216–>10,000 (Ki) 107–2,140 (EC50) 62–108% (Emax) |
| 5-HT2B | 148–551 (Ki) 257–708 (EC50) 53–105% (Emax) |
| 5-HT2C | 177–4,366 (Ki) 741–2,450 (EC50) 68–112% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT4 | ND |
| 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 (EC50) 24–88% (Emax) |
| D5 | >10,000 |
| H1–H4 | >10,000 |
| M1–M5 | >10,000 |
| TAAR1 | ND |
| I1 | ND |
| σ1, σ2 | >10,000 |
| SERT | >10,000 (Ki) ND (IC50) |
| NET | >10,000 (Ki) ND (IC50) |
| DAT | >10,000 (Ki) ND (IC50) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [5][6][7] | |
The comprehensive receptor interactions of escaline have been described.[5] 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.[5] The drug is also an agonist of the dopamine D4 receptor, though not of any other dopamine receptors.[5] Besides escaline, the receptor interactions of various escaline analogues and derivatives have been described.[8]
Escaline produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[9][3] It partially substitutes for LSD in rodent drug discrimination tests.[10][9][7] The drug is unusual among serotonergic psychedelics in only partially rather than fully substituting for LSD.[10][9][7]
Chemistry
Synthesis
The chemical synthesis of escaline has been described.[1]
Analogues
Analogues of escaline include mescaline, proscaline, allylescaline, methallylescaline, 3C-E, and 3-methoxy-4-ethoxyphenethylamine (MEPEA; 3-desmethoxyescaline), among others.[1]
History
Escaline was first described in the scientific literature by George S. Grace in 1934.[11] Subsequently, it was also described by F. Benington and colleagues in 1954.[12] It was later further described by Otakar Leminger in 1972.[13] 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.[14][15]
Society and culture
Legal status
Canada
Escaline is not a controlled substance in Canada as of 2025.[16]
Sweden
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).[18][19]