Aleph (psychedelic)

Aleph
Names
Preferred IUPAC name
1-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
Other names
2,5-Dimethoxy-4-methylthioamphetamine
1-(4-Methylthio-2,5-dimethoxyphenyl)-2-aminopropane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C12H19NO2S/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3 checkY
    Key: COBYBOVXXDQRAU-UHFFFAOYSA-N checkY
  • InChI=1/C12H19NO2S/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3
    Key: COBYBOVXXDQRAU-UHFFFAOYAK
  • C1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC
  • O(c1cc(c(OC)cc1SC)CC(N)C)C
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Aleph (also known as DOT or 2,5-dimethoxy-4-methylthioamphetamine) is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.[1]

Like many other psychedelics, aleph is a partial agonist at the 5-HT2A receptor (EC50 = 10 nM).[2] It has weak MAO-A inhibitory activity with an IC50 of 5.2 μM. For reference, amphetamine has an IC50 of 11 μM and 4-methylthioamphetamine has a value of 0.2 μM.[3] A lower number indicates stronger inhibition.

  1. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology. 240 (1): 115–126. doi:10.1007/s00213-022-06279-2. PMC 9816194. PMID 36477925.
  3. ^ Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". Journal of Medicinal Chemistry. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID 15801832.