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Aleph (psychedelic)
| Field | Value | ||||
|---|---|---|---|---|---|
| Verifiedfields | verified | ||||
| Watchedfields | verified | ||||
| verifiedrevid | 477314818 | ||||
| drug_name | Aleph | ||||
| image | Aleph psychedelic.svg | ||||
| image_class | skin-invert-image | ||||
| width | 225px | ||||
| image2 | Aleph ball-and-stick structure.png | ||||
| image_class2 | bg-transparent | ||||
| width2 | 200px | ||||
| routes_of_administration | Oral | ||||
| class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen | ||||
| ATC_prefix | None | ||||
| duration_of_action | 6–8 hours | ||||
| CAS_number_Ref | |||||
| CAS_number | 61638-07-1 | ||||
| PubChem | 143828 | ||||
| ChemSpiderID_Ref | |||||
| ChemSpiderID | 126887 | ||||
| UNII_Ref | |||||
| UNII | C9ZVF4O01N | ||||
| ChEMBL_Ref | |||||
| ChEMBL | 447830 | ||||
| synonyms | Aleph; Aleph-1; ALEPH; ALEPH-1; DOT; DOT-1; Para-DOT; 4-Methylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methylthioamphetamine; 4-MeS-DMA | ||||
| IUPAC_name | 1-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine | ||||
| C | 12 | H=19 | N=1 | O=2 | S=1 |
| SMILES | C1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC | ||||
| StdInChI_Ref | |||||
| StdInChI | 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 | ||||
| StdInChIKey_Ref | |||||
| StdInChIKey | COBYBOVXXDQRAU-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life =
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. It is one of the Aleph series of compounds.
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph's dose range as 5 to 10mg orally and its duration as 6 to 8hours. 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.
Interactions
Pharmacology
Pharmacodynamics
Aleph is known to be a partial agonist of the serotonin 5-HT2A receptor ( = 10–66nM; = 114–191%).
It has weak MAO-A inhibitory activity with an of 5.2μM. For comparison, amphetamine has an IC50 of 11μM and 4-methylthioamphetamine (4-MTA) has a value of 0.2μM.
Chemistry
Synthesis
The chemical synthesis of Aleph has been described.
Derivatives
Derivatives of Aleph include Aleph-2, Aleph-4, Aleph-6, and Aleph-7. 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.
History
Aleph was first tested by Alexander Shulgin in 1975. It was first described in the scientific literature by Shulgin and David E. Nichols in 1976. Its properties and effects in humans were described by them in 1978. Subsequently, the drug was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
Society and culture
Names
Aleph was named by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. Another earlier name of the drug is para-DOT.
Legal status
Canada
Aleph is a controlled substance in Canada under phenethylamine blanket-ban language.
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.
References
References
- {{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal003.shtml
- (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology.
- (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci.
- (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.
- (October 1976). "Sulfur analogs of psychotomimetic amines". J Pharm Sci.
- (October 1977). "Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane". J Med Chem.
- (1978). "The Psychopharmacology of Hallucinogens". Elsevier.
- "Controlled Drugs and Substances Act".
- (January 2023). "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". Drug Enforcement Administration, U.S. Department of Justice.
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