Aleph (psychedelic) explained

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, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.

Like many other psychedelics, aleph is a partial agonist at the 5-HT_2A receptor (EC₅₀ = 10 nM).^[1] It has weak MAO-A inhibitory activity with an IC₅₀ of 5.2 μM. For reference, amphetamine has an IC₅₀ of 11 μM and 4-methylthioamphetamine has a value of 0.2 μM.^[2] A lower number indicates stronger inhibition.

Homologues

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

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

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)

CAS number: 952006-44-9

SMILES: C1(=C(C=C(C(=C1)SC2=CC=CC=C2)OC)CC(C)N)OC=DSC4R=5SC4_5⁶

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)SC4^4

Legality

In the United States Aleph is a Schedule 1 controlled substance as a positional isomer of 2C-T-4 and 2C-T-7^[3]

See also

• 2,5-Dimethoxy-4-substituted amphetamines

External links

• Aleph Entry in PiHKAL
• ALEPH Entry at PiHKAL·info
• Aleph-2 Entry in PiHKAL
• ALEPH-2 Entry at PiHKAL·info
• Aleph-4 Entry in PiHKAL
• ALEPH-4 Entry at PiHKAL·info
• Aleph-6 Entry in PiHKAL
• ALEPH-6 Entry at PiHKAL·info
• Aleph-7 Entry in PiHKAL
• ALEPH-7 Entry at PiHKAL·info

Notes and References

1. Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME . Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines . Psychopharmacology . 240 . 1 . 115–126 . January 2023 . 36477925 . 9816194 . 10.1007/s00213-022-06279-2 .
2. Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE . 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 . April 2005 . 15801832 . 10.1021/jm0493109 .
3. Web site: Lists of: Scheduling Actions Controlled Substances Regulated Chemicals . January 2023 . Drug and Chemical Evaluation Section, Diversion Control Division . Drug Enforcement Administration, U.S. Department of Justice .