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Aleph (psychedelic)


FieldValue
Verifiedfieldsverified
Watchedfieldsverified
verifiedrevid477314818
drug_nameAleph
imageAleph psychedelic.svg
image_classskin-invert-image
width225px
image2Aleph ball-and-stick structure.png
image_class2bg-transparent
width2200px
routes_of_administrationOral
classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC_prefixNone
duration_of_action6–8 hours
CAS_number_Ref
CAS_number61638-07-1
PubChem143828
ChemSpiderID_Ref
ChemSpiderID126887
UNII_Ref
UNIIC9ZVF4O01N
ChEMBL_Ref
ChEMBL447830
synonymsAleph; Aleph-1; ALEPH; ALEPH-1; DOT; DOT-1; Para-DOT; 4-Methylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methylthioamphetamine; 4-MeS-DMA
IUPAC_name1-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
C12H=19N=1O=2S=1
SMILESC1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC
StdInChI_Ref
StdInChI1S/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
StdInChIKeyCOBYBOVXXDQRAU-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.

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

  1. {{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal003.shtml
  2. (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology.
  3. (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci.
  4. (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.
  5. (October 1976). "Sulfur analogs of psychotomimetic amines". J Pharm Sci.
  6. (October 1977). "Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane". J Med Chem.
  7. (1978). "The Psychopharmacology of Hallucinogens". Elsevier.
  8. "Controlled Drugs and Substances Act".
  9. (January 2023). "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". Drug Enforcement Administration, U.S. Department of Justice.
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