Aleph (psychedelic)

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Aleph
Aleph psychedelic.svg
Clinical data
Other namesAleph; Aleph-1; ALEPH; ALEPH-1; DOT; DOT-1; Para-DOT; 4-Methylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methylthioamphetamine; 4-MeS-DMA
Routes of
administration 		Oral [1]
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action 6–8 hours [1]
Identifiers
  • 1-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H19NO2S
Molar mass 241.35 g·mol−1
3D model (JSmol)
  • C1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC
  • 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 Yes check.svgY
  • Key:COBYBOVXXDQRAU-UHFFFAOYSA-N Yes check.svgY
   (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 phenethylamine, amphetamine, and DOx families. [1] It is one of the Aleph series of compounds. [1]

Contents

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph's dose range as 5 to 10 mg orally and its duration as 6 to 8 hours. [1] The effects of Aleph have been reported to include simple tasks feeling "alien", intense intellectual stimulation, impairment, a sensation of pleasant physical warmth, and an afterglow including feelings of empathy for everything. [1]

Interactions

Pharmacology

Pharmacodynamics

Aleph is known to be a partial agonist of the serotonin 5-HT2A receptor (EC50 Tooltip half-maximal effective concentration = 10 nM). [2]

It has weak MAO-A inhibitory activity with an IC50 Tooltip half-maximal inhibitory concentration of 5.2 μM. [3] For comparison, amphetamine has an IC50 of 11 μM and 4-methylthioamphetamine (4-MTA) has a value of 0.2 μM. [3]

Chemistry

Synthesis

The chemical synthesis of Aleph has been described. [1]

Derivatives

Derivatives of Aleph include Aleph-2, Aleph-4, Aleph-6, and Aleph-7. [1] The Aleph series of compounds are the DOx or amphetamine analogues of 2C-T, 2C-T-2, 2C-T-4, 2C-T-6, and 2C-T-7, respectively. [1]

History

Aleph was first tested by Alexander Shulgin in 1975. [1] It was first described in the scientific literature by Shulgin and David E. Nichols in 1976. [4] [5] Its properties and effects in humans were described by them in 1978. [6] Subsequently, the drug was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1]

Society and culture

Names

Aleph was named by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. [1] Another earlier name of the drug is para-DOT. [1] [6]

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. [7]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://erowid.org/library/books_online/pihkal/pihkal003.shtml
  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. 1 2 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.
  4. ↑ Nichols DE, Shulgin AT (October 1976). "Sulfur analogs of psychotomimetic amines". J Pharm Sci. 65 (10): 1554–1556. doi:10.1002/jps.2600651040. PMID   978423.
  5. ↑ Jacob P, Anderson G, Meshul CK, Shulgin AT, Castagnoli N (October 1977). "Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane". J Med Chem. 20 (10): 1235–1239. doi:10.1021/jm00220a001. PMID   903913.
  6. 1 2 Shulgin AT, Nichols DE (1978). "Characterization of Three New Psychotomimetics". In Stillman RC, Willette RE (eds.). The Psychopharmacology of Hallucinogens. Elsevier. pp. 74–83. doi:10.1016/b978-0-08-021938-7.50010-2. ISBN   978-0-08-021938-7.
  7. ↑ "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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