Aleph (psychedelic)

Aleph
Clinical data
Other namesAleph; Aleph-1; ALEPH; ALEPH-1; DOT; DOT-1; Para-DOT; 2,5-Dimethoxy-4-methylthioamphetamine; 4-Methylthio-2,5-dimethoxyamphetamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action6–8 hours[1]
Identifiers
IUPAC name
  • 1-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO2S
Molar mass241.35 g·mol−1
3D model (JSmol)
SMILES
  • C1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC
InChI
  • 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
  (verify)

Aleph, or Aleph-1, also known as DOT or para-DOT or as 4-methylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the amphetamine and DOx families.[1]

Use and effects

Aleph was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dose range as 5 to 10 mg orally, with effects typically lasting for 6 to 8 hours.[1]

Interactions

Pharmacology

Pharmacodynamics

Like many other psychedelics, Aleph is a partial agonist at the 5-HT2A receptor (EC50 = 10 nM).[2][3] 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.[4]

List of Aleph drugs

Aleph-2

Aleph-2

Dosage: 4–8 mg

Duration: 8–16 hours

Effects: Strong visuals

2C analog: 2C-T-2

CAS number: 185562-00-9

SMILES: C1(=C(C=C(C(=C1)SCC)OC)CC(C)N)OC

Aleph-4

Aleph-4

Dosage: 7–12 mg

Duration: 12–20 hours

Effects: "profound and deep learning experiences" - Alexander Shulgin

2C analog: 2C-T-4

CAS number: 123643-26-5

SMILES: C1(=C(C=C(C(=C1)SC(C)C)OC)CC(C)N)OC

Aleph-6

Aleph-6

Dosage: 40 mg or more

Duration: very long, unspecified

Effects: enhances other psychoactive drugs, similar to 2C-D

2C analog: 2C-T-6 (has never been synthesized)

CAS number: 952006-44-9

SMILES: C1(=C(C=C(C(=C1)SC2=CC=CC=C2)OC)CC(C)N)OC=DSC4 R=5SC456

Aleph-7

Aleph-7

Dosage: 4–7 mg

Duration: 15–30 hours

2C analog: 2C-T-7

CAS number: 207740-16-7

SMILES: C1(=C(C=C(C(=C1)SC4^4

Society and culture

United States

In the United States, Aleph is a Schedule 1 controlled substance as a positional isomer of 2C-T-4 and 2C-T-7.[5]

See also

References

  1. 1 2 3 4 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. ↑ 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" (PDF). Psychopharmacology (Berl). 240 (1): 115–126. doi:10.1007/s00213-022-06279-2. PMC 9816194. PMID 36477925.
  4. ↑ 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.
  5. ↑ "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). Drug and Chemical Evaluation Section, Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice. January 2023.
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