Aleph-2
Pharmaceutical compound
From Wikipedia, the free encyclopedia
Aleph-2, or ALEPH-2, also known as 4-ethylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.[1][2][3] It is one of the Aleph series of compounds.[1] The drug was encountered as a novel designer drug in Europe in 2023.[4]
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| Other names | ALEPH-2; DOT-2; 4-Ethylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-EtS-DMA |
| Routes of administration | Oral[1][2] |
| Drug class | Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist |
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| Duration of action | 8–16 hours[1][2] |
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| Formula | C13H21NO2S |
| Molar mass | 255.38 g·mol−1 |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph-2's dose as 4 to 8 mg orally and its duration as 8 to 16 hours.[1][2] The effects of Aleph-2 have been reported to include "almost no visual phenomena" to "extraordinary visuals and interpretations", visual distortion and movement, enhanced auditory and tactile perception, and a sensation of physical warmth, and residual shakiness and muscle tremors, among others.[1][2] There is an unpredictability with the dosing and effects of Aleph-2, such that one person who took 4 mg had strong effects including ending up in a fetal position, in relative hibernation for several hours, and with substantial amnesia, whereas another person who took 8 mg experienced only a bare threshold including slight lightheadedness.[1]
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 1,674 |
| 5-HT1B | 2,037 |
| 5-HT1D | 1,532 |
| 5-HT1E | 3,088 |
| 5-HT1F | ND |
| 5-HT2A | 60.4 (Ki) 0.489–0.898 (EC50) 104–108% (Emax) |
| 5-HT2B | 1.6 |
| 5-HT2C | 50.3 (Ki) 0.0912–0.401 (EC50) 105–114% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT4 | ND |
| 5-HT5A | >10,000 |
| 5-HT6 | 3,020 |
| 5-HT7 | 1,322 |
| α1A | >10,000 |
| α1B | >10,000 |
| α1D | ND |
| α2A | 5,803 |
| α2B | 2,934 |
| α2C | 1,388 |
| β1 | 6,792 |
| β2 | 26.1 |
| β3 | ND |
| D1, D2 | >10,000 |
| D3 | 618.3 |
| D4, D5 | >10,000 |
| H1–H4 | >10,000 |
| M1, M2 | >10,000 |
| M3 | 1,907 |
| M4 | >10,000 |
| M5 | 8,018 |
| I1 | 319.8 |
| σ1 | 238.9 |
| σ2 | >10,000 |
| TAAR1 | ND |
| SERT | 1,318 (Ki) |
| NET | >10,000 (Ki) |
| DAT | >10,000 (Ki) |
| MAO-A | 3,200–3,800 (IC50) (rat) |
| MAO-B | >100,000 (IC50) (rat) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [5][6][3][7][8][9] | |
Aleph-2 acts as a serotonin 5-HT2 receptor agonist.[3][10] The drug is also a weak monoamine oxidase inhibitor (MAOI), with IC50 values of 3,200 nM for monoamine oxidase A (MAO-A) and >100,000 nM for monoamine oxidase B (MAO-B).[7][8] Aleph-2 produces anxiolytic effects in rodents.[10][11][12]
Chemistry
History
Aleph-2 was first described in the scientific literature by Alexander Shulgin in 1978.[13][14][15][16] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1] Aleph-2 was encountered as a novel designer drug in Europe in 2023.[4]
Society and culture
Legal status
Canada
Aleph-2 is a controlled substance in Canada under phenethylamine blanket-ban language.[17]
United States
Aleph-2 is not an explicitly controlled substance in the United States.[18][2] However, it is a Schedule I controlled substance in this country as an isomer of 2C-T-4.[18][19]