From Surf Wiki (app.surf) — the open knowledge base
Aleph-2
| Field | Value | ||||
|---|---|---|---|---|---|
| image | Aleph-2.svg | ||||
| image_class | skin-invert-image | ||||
| width | 250px | ||||
| routes_of_administration | Oral | ||||
| class | Serotonergic psychedelic; Hallucinogen; Serotonin [5-HT2 receptor](5-ht2-receptor) agonist | ||||
| ATC_prefix | None | ||||
| duration_of_action | 8–16hours | ||||
| CAS_number | 185562-00-9 | ||||
| PubChem | 10264356 | ||||
| DrugBank | DB13940 | ||||
| ChemSpiderID | 8439835 | ||||
| UNII | Z1I419DRZZ | ||||
| ChEMBL | 339611 | ||||
| synonyms | ALEPH-2; DOT-2; 4-Ethylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-EtS-DMA | ||||
| IUPAC_name | 1-(4-ethylsulfanyl-2,5-dimethoxyphenyl)propan-2-amine | ||||
| C | 13 | H=21 | N=1 | O=2 | S=1 |
| SMILES | CCSC1=C(C=C(C(=C1)OC)CC(C)N)OC | ||||
| StdInChI | 1S/C13H21NO2S/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 | ||||
| StdInChIKey | MCYCODJKXUJSAT-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life =
Aleph-2, or ALEPH-2, also known as 4-ethylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is one of the Aleph series of compounds. The drug was encountered as a novel designer drug in Europe in 2023.
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph-2's dose as 4 to 8mg orally and its duration as 8 to 16hours. 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. There is an unpredictability with the dosing and effects of Aleph-2, such that one person who took 4mg 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 8mg experienced only a bare threshold including slight lightheadedness.
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | 1,674 |
| [5-HT1B](5-ht1b-receptor) | 2,037 |
| [5-HT1D](5-ht1d-receptor) | 1,532 |
| [5-HT1E](5-ht1e-receptor) | 3,088 |
| [5-HT1F](5-ht1f-receptor) | ND |
| [5-HT2A](5-ht2a-receptor) | 60.4 (Ki) |
| 0.489–0.898 () | |
| 104–108% () | |
| [5-HT2B](5-ht2b-receptor) | 1.6 |
| [5-HT2C](5-ht2c-receptor) | 50.3 (Ki) |
| 0.0912–0.401 (EC50) | |
| 105–114% (Emax) | |
| [5-HT3](5-ht3-receptor) | 10,000 |
| [5-HT4](5-ht4-receptor) | ND |
| [5-HT5A](5-ht5a-receptor) | 10,000 |
| [5-HT6](5-ht6-receptor) | 3,020 |
| [5-HT7](5-ht7-receptor) | 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 |
| ND | |
| 1,318 (Ki) | |
| 10,000 (Ki) | |
| 10,000 (Ki) | |
| 3,200–3,800 (IC50) (rat) | |
| 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:** |
Aleph-2 acts as a serotonin 5-HT2 receptor agonist. The drug is also a weak monoamine oxidase inhibitor (MAOI), with values of 3,200nM for monoamine oxidase A (MAO-A) and 100,000nM for monoamine oxidase B (MAO-B). Aleph-2 produces anxiolytic effects in rodents.
Chemistry
Synthesis
The chemical synthesis of Aleph-2 has been described.
Analogues
Analogues of Aleph-2 include Aleph, Aleph-4, Aleph-6, Aleph-7, and 2C-T-2, among others.
History
Aleph-2 was first described in the scientific literature by Alexander Shulgin in 1978. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Aleph-2 was encountered as a novel designer drug in Europe in 2023.
Society and culture
Legal status
Canada
Aleph-2 is a controlled substance in Canada under phenethylamine blanket-ban language.
United States
Aleph-2 is not an explicitly controlled substance in the United States. However, it is a Schedule I controlled substance in this country as an isomer of 2C-T-4.
References
References
- (1991). "PiHKAL: A Chemical Love Story". Transform Press.
- (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". Transform Press.
- (1 May 1996). "ALEPH-2".
- (1 April 2025). "Kᵢ Database".
- "BDBM50164337 2-(4-Ethylsulfanyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL339611". BindingDB.
- (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol.
- (December 1997). "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships". Biochem Pharmacol.
- (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". J Med Chem.
- (February 2010). "Psychedelics and the human receptorome". PLOS ONE.
- (November 2000). "ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2a and 5-HT2c receptor agonist". Life Sciences.
- (June 1996). "Behavioral effects of the putative anxiolytic (+/-)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice". Pharmacology, Biochemistry, and Behavior.
- (November 1996). "(+/-)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology.
- (1978). "Stimulants". Springer US.
- (1978). "QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens". National Institute on Drug Abuse.
- (1980). "Burger's Medicinal Chemistry". Wiley.
- (1982). "Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs". Springer Berlin Heidelberg.
- "Controlled Drugs and Substances Act".
- (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
- [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".
This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.
Ask Mako anything about Aleph-2 — get instant answers, deeper analysis, and related topics.
Research with MakoFree with your Surf account
Create a free account to save articles, ask Mako questions, and organize your research.
Sign up freeThis content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.
Report