Aleph (psychedelic)

Aleph (also known as DOT or 2,5-dimethoxy-4-methylthioamphetamine) is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg.[1] According to Shulgin, the effects of aleph typically last for 6 to 8 hours.

Aleph
Names
IUPAC name
2-[2,5-Dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
Other names
2,5-Dimethoxy-4-methylthioamphetamine
1-(4-Methylthio-2,5-dimethoxyphenyl)-2-aminopropane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
Properties
C12H19NO2S
Molar mass 241.35 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It has weak MAO-A inhibition activity with an IC50 of 5.2 mmol. For reference, amphetamine has an IC50 of 11 mmol and 4-methylthioamphetamine has a value of 0.2 mmol.[2] A lower number indicates a stronger inhibitor.

Homologues

Aleph-2
Aleph-2

Dosage: 7–12 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)

SMILES: C1(=C(C=C(C(=C1)SC2=CC=CC=C2)OC)CC(C)N)OC

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)SCCC)OC)CC(C)N)OC

See also

References
  1. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. Gallardo-Godoy, Alejandra; Fierro, Angélica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E. (2005). "Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling". Journal of Medicinal Chemistry. 48 (7): 2407. doi:10.1021/jm0493109. PMID 15801832.
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