Aleph (psychedelic)

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Aleph (psychedelic)
2,5-dimethoxy-4-methylthioamphetamine.svg
Names
IUPAC name
2-(2,5-Dimethoxy-4-methylsulfanyl-phenyl)-1-methylethylamine
Other names
2,5-Dimethoxy-4-methylthioamphetamine
1-(4-Methylthio-2,5-dimethoxyphenyl)-2-aminopropane
Identifiers
61638-07-1 N
ChEMBL ChEMBL447830 YesY
ChemSpider 126887 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 143828
Properties
C12H19NO2S
Molar mass 240.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Aleph, 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 (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 5–10 mg.[1] According to Shulgin, the effects of aleph typically last for 6 to 8 hours.

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

Homologues[edit]

Aleph-2[edit]

Aleph-2


Dosage: 4-8 mgs

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[edit]

Aleph-4


Dosage: 7-12 mgs

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[edit]

Aleph-6


Dosage: 40 mgs 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[edit]

Aleph-7


Dosage: 4-7 mgs

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[edit]

References[edit]

  1. ^ Shulgin, Alexander; Ann Shulgin (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. 

External links[edit]