Community hub
0 subscribers8 pages, 0 posts
Recent from talks
All channels
Be the first to start a discussion here.
Be the first to start a discussion here.
Be the first to start a discussion here.
Be the first to start a discussion here.
Contribute something
Welcome to the community hub built to collect knowledge and have discussions related to Aleph-2.
Nothing was collected or created yet.
Aleph-2
View on Wikipediafrom Wikipedia
 | |
| Clinical data | |
|---|---|
| Other names | ALEPH-2; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-Ethylthio-2,5-dimethoxyamphetamine; DOT-2 |
| Routes of administration | Oral[1][2] |
| Drug class | Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist |
| Pharmacokinetic data | |
| Duration of action | 8–16 hours[1][2] |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C13H21NO2S |
| Molar mass | 255.38 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Aleph-2, or ALEPH-2, also known as 2,5-dimethoxy-4-ethylthioamphetamine, is a serotonergic psychedelic of the phenethylamine, amphetamine, and DOx families.[1][2][3]
Use and effects
[edit]According to Alexander Shulgin, its dosage is 4 to 8 mg orally and its duration is 8 to 16 hours.[1][2] The drug is said to produce strong visuals.[1][2]
Pharmacology
[edit]| 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: [4][5][3][6][7][8] | |
Aleph-2 acts as a serotonin 5-HT2 receptor agonist.[3][9] 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).[6][7] Aleph-2 produces anxiolytic effects in rodents.[9][10][11]
See also
[edit]References
[edit]- ^ a b c d e Shulgin T, Shulgin A (1991). "#4 ALEPH-2 2,5-DIMETHOXY-4-ETHYLTHIOAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. pp. 464–467. ISBN 978-0-9630096-0-9. OCLC 25627628.
- ^ a b c d e Shulgin A, Manning T, Daley PF (2011). "#4. ALEPH-2". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. p. 5. ISBN 978-0-9630096-3-0. OCLC 709667010.
- ^ a b c Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2) e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
- ^ "Kᵢ Database". PDSP. 1 April 2025. Retrieved 1 April 2025.
- ^ Liu T. "BindingDB BDBM50164337 2-(4-Ethylsulfanyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL339611". BindingDB. Retrieved 1 April 2025.
- ^ a b Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
- ^ a b Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M (December 1997). "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships" (PDF). Biochem Pharmacol. 54 (12): 1361–1369. doi:10.1016/s0006-2952(97)00405-x. PMID 9393679.
- ^ Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, et al. (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. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID 15801832.
- ^ a b Acuña-Castillo C, Scorza C, Reyes-Parada M, Cassels BK, Huidobro-Toro JP (November 2000). "ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2a and 5-HT2c receptor agonist". Life Sciences. 67 (26): 3241–3247. doi:10.1016/s0024-3205(00)00906-1. PMID 11191631.
- ^ Scorza MC, Reyes-Parada M, Silveira R, Viola H, Medina JH, Viana MB, et al. (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. 54 (2): 355–361. doi:10.1016/0091-3057(95)02149-3. PMID 8743595.
- ^ Reyes-Parada M, Scorza C, Romero V, Silveira R, Medina JH, Andrus D, et al. (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. 354 (5): 579–585. doi:10.1007/BF00170831. PMID 8938655.