Aleph-2

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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
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

It acts as a serotonin 5-HT2 receptor agonist. [3] [4] 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). [5] [6] Aleph-2 produces anxiolytic effects in rodents. [4] [7] [8]

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 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. 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.
  5. ↑ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Frontiers in Pharmacology. 10: 1590. doi: 10.3389/fphar.2019.01590 . PMC   6989591 . PMID   32038257.
  6. ↑ 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". Biochemical Pharmacology. 54 (12): 1361–1369. doi:10.1016/s0006-2952(97)00405-x. PMID   9393679.
  7. ↑ 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.
  8. ↑ 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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