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In 1968 Shirley Chisholm became the first Black woman elected to the United States Congress. In 1972 she launched a campaign for the Democratic presidential nomination, breaking another political barrier.
MORE →Reflects the personal views, recollections, and perspective of the author, Mike Davis.
This is a personal recollection on the Move fire on May 13, 1985
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| Clinical data | |
|---|---|
| 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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| Pharmacokinetic data | |
| Duration of action | 8–12 hours[1] |
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| Chemical and physical data | |
| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 165 to 166 °C (329 to 331 °F) (hydrochloride) |
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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]
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]
| 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]
The chemical synthesis of escaline has been described.[1]
Analogues of escaline include mescaline, proscaline, allylescaline, methallylescaline, 3C-E, and 3-methoxy-4-ethoxyphenethylamine (MEPEA; 3-desmethoxyescaline), among others.[1]
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]
Escaline is not a controlled substance in Canada as of 2025.[16]
Escaline is illegal in Sweden as of 26 January 2016.[17]
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]
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In the case of the 3,4,5- trioxygenated compounds, binding studies at 5-HT2A and 5-HT2C receptors revealed somewhat higher affinities than mescaline but, in phosphoinositide hydrolysis assays (only for 5-HT2A), lower efficacies relative to serotonin and the full agonist mescaline (60 and 45%, respectively). More striking, however, was the observation that the new compounds did not fully substitute for LSD in LSD-trained rats, and at doses well above the mescaline EC50, only 50 and 29% appropriate responding was recorded. In view of this unexpected result, 3,5-dimethoxy-4-ethoxyphenethylamine (escaline), which is considerably more potent than mescaline in humans,128 was also tested. It was found to have about twice the affinity of mescaline for 5-HT2A receptors and was a complete agonist with very similar functional potency, but again it failed to substitute completely for LSD in the drug discrimination experiments.
{{cite journal}}: CS1 maint: bot: original URL status unknown (link)
Source: Wikipedia. Article content is retrieved live through the MediaWiki API.
Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. 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.
NBOMe-escaline, also known as escaline-NBOMe or as N-(2-methoxybenzyl)-4-ethoxy-3,5-dimethoxyphenethylamine, is a serotonin receptor agonist and putative psychedelic drug of the phenethylamine, scaline, and N-benzylphenethylamine (NBOMe) families. It is the N-(2-methoxybenzyl) derivative of escaline. The drug acts as a potent serotonin 5-HT2A receptor partial agonist, with an affinity (A2) of 0.537 nM, an activational potency (KP) of 7.08 nM, and an intrinsic activity (EmaxTooltip maximal efficacy) of 48%. As a serotonin 5-HT2A receptor agonist in vitro, it was 7-fold more potent than NBOMe-mescaline, 50-fold more potent than escaline, and 476-fold more potent than mescaline. NBOMe-escaline was first described in the scientific literature by Heinz Pertz and colleagues by 1999. Along with NBOMe-mescaline, it was one of the first psychedelic N-benzylphenethylamines to be discovered, slightly preceding the publication of 25-NB drugs like 25I-NBOMe by the same group of researchers. NBOMe-escaline is not a controlled substance in Canada as of 2025.
Metaescaline (ME), also known as 3-ethoxy-4,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is the analogue of mescaline in which the methoxy group at the 3 position has been replaced with an ethoxy group. 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.
Methallylescaline (MAL), also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is taken orally. The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor. It is closely structurally related to mescaline and to other scalines like escaline and allylescaline. Methallylescaline was first described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). It was encountered as a novel designer drug by 2013.
Before the 1921 destruction of Tulsa’s Greenwood District, Black residents had created a remarkable center of business and community life. The district included stores, professional offices, entertainment venues and homes owned by Black citizens. Understanding Greenwood means learning what was built—not only what was burned.
MORE →Brown v. Board of Education in 1954.