Aleph (psychedelic)
Pharmaceutical compound
Aleph
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 classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action6–8 hours[1]
Identifiers
  • 1-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
CAS Number
  • 61638-07-1 checkY
PubChem CID
  • 143828
ChemSpider
  • 126887 checkY
UNII
  • C9ZVF4O01N
ChEMBL
  • ChEMBL447830 checkY
CompTox Dashboard (EPA)
  • DTXSID80874362
Chemical and physical data
FormulaC12H19NO2S
Molar mass241.35 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 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 phenethylamine, amphetamine, and DOx families.[1] It is one of the Aleph series of compounds.[1]

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 (EC50Tooltip half-maximal effective concentration = 10–66 nM; EmaxTooltip maximal efficacy = 114–191%).[2][3]

It has weak MAO-A inhibitory activity with an IC50Tooltip half-maximal inhibitory concentration of 5.2 μM.[4] For comparison, amphetamine has an IC50 of 11 μM and 4-methylthioamphetamine (4-MTA) has a value of 0.2 μM.[4]

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.[5][6] Its properties and effects in humans were described by them in 1978.[7] 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][7]

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.[8]

See also

References

  1. ^ a b c d e f g h i j k l m 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. ^ Pottie E, Poulie CB, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, Gloriam DE, Jensen AA, Kristensen JL, Stove CP (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci. 14 (15): 2727–2742. doi:10.1021/acschemneuro.3c00267. PMID 37474114.
  4. ^ a b 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. ^ 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.
  6. ^ 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.
  7. ^ a b 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.
  8. ^ "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.
  • Aleph - Isomer Design
  • Aleph - PiHKAL - Erowid
  • Aleph - PiHKAL - Isomer Design
  • Aleph - The Shulgin Index
  • The Big & Dandy DOT/Aleph-1 Thread - Bluelight
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