Aleph-2

Last updated

Aleph-2
2,5-dimethoxy-4-ethylthioamphetamine.svg
Clinical data
Other namesALEPH-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
  • 1-(4-ethylsulfanyl-2,5-dimethoxyphenyl)propan-2-amine
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)
  • CCSC1=C(C=C(C(=C1)OC)CC(C)N)OC
  • InChI=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
  • Key:MCYCODJKXUJSAT-UHFFFAOYSA-N

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]

Contents

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 Tooltip half-maximal effective concentration)
104–108% (Emax Tooltip maximal efficacy)
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 Tooltip Trace amine-associated receptor 1ND
SERT Tooltip Serotonin transporter1,318 (Ki)
NET Tooltip Norepinephrine transporter>10,000 (Ki)
DAT Tooltip Dopamine transporter>10,000 (Ki)
MAO-A Tooltip Monoamine oxidase A3,200–3,800 (IC50) (rat)
MAO-B Tooltip Monoamine oxidase 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 Tooltip half-maximal inhibitory concentration 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 2 3 4 5 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.
  2. 1 2 3 4 5 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.
  3. 1 2 3 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.
  4. ↑ "Kᵢ Database". PDSP. 1 April 2025. Retrieved 1 April 2025.
  5. ↑ Liu T. "BindingDB BDBM50164337 2-(4-Ethylsulfanyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL339611". BindingDB. Retrieved 1 April 2025.
  6. 1 2 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.
  7. 1 2 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.
  8. ↑ 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.
  9. 1 2 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.
  10. ↑ 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.
  11. ↑ 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.
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