Chemistry:Aleph-2

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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

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

Aleph-2 activities
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

References

  1. ↑ 1.0 1.1 1.2 "#4 ALEPH-2 2,5-DIMETHOXY-4-ETHYLTHIOAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. 1991. pp. 464–467. ISBN 978-0-9630096-0-9. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal004.shtml. 
  2. ↑ 2.0 2.1 2.2 "#4. ALEPH-2". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley, CA: Transform Press. 2011. pp. 5. ISBN 978-0-9630096-3-0. OCLC 709667010. https://archive.org/details/shulgin-index-vol-1/page/5/mode/1up. 
  3. ↑ 3.0 3.1 3.2 "Psychedelics and the human receptorome". PLOS ONE 5 (2). February 2010. doi:10.1371/journal.pone.0009019. PMID 20126400. Bibcode: 2010PLoSO...5.9019R. 
  4. ↑ "Kᵢ Database". 1 April 2025. https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12945&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=. 
  5. ↑ Liu, Tiqing. "BindingDB BDBM50164337 2-(4-Ethylsulfanyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL339611". https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50164337. 
  6. ↑ 6.0 6.1 "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol 10. 2019. doi:10.3389/fphar.2019.01590. PMID 32038257. 
  7. ↑ 7.0 7.1 "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships". Biochem Pharmacol 54 (12): 1361–1369. December 1997. doi:10.1016/s0006-2952(97)00405-x. PMID 9393679. https://mrtoasted.com/~vaaguh/maoi-properties-of-methoxylated-and-alkylthioamp-derivates.pdf. 
  8. ↑ "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. April 2005. doi:10.1021/jm0493109. PMID 15801832. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=61e1af109f88d1c41da1f218f9403dff12b5d98d. 
  9. ↑ 9.0 9.1 "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. November 2000. doi:10.1016/s0024-3205(00)00906-1. PMID 11191631. 
  10. ↑ "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. June 1996. doi:10.1016/0091-3057(95)02149-3. PMID 8743595. 
  11. ↑ "(+/-)-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. November 1996. doi:10.1007/BF00170831. PMID 8938655. 

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