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
Preferred IUPAC name 1-[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
CAS Number	61638-07-1^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL447830^Y
ChemSpider	126887^Y
PubChem CID	143828
UNII	C9ZVF4O01N^Y
CompTox Dashboard (EPA)	DTXSID80874362
InChI InChI=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^Y Key: COBYBOVXXDQRAU-UHFFFAOYSA-N^Y InChI=1/C12H19NO2S/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3 Key: COBYBOVXXDQRAU-UHFFFAOYAK
SMILES C1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC O(c1cc(c(OC)cc1SC)CC(N)C)C
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

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

 

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

• 2,5-Dimethoxy-4-substituted amphetamines

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): 2407–2419. doi:10.1021/jm0493109. PMID 15801832.

External links

• Aleph Entry in PiHKAL
• Aleph-2 Entry in PiHKAL
• Aleph-4 Entry in PiHKAL
• Aleph-6 Entry in PiHKAL
• Aleph-7 Entry in PiHKAL