Aleph (psychedelic)

For other uses, see Aleph (disambiguation).

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.^[1] It is one of the Aleph series of compounds.^[1]

Aleph

Clinical data
Other names	Aleph; Aleph-1; ALEPH; ALEPH-1; DOT; DOT-1; Para-DOT; 4-Methylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-methylthioamphetamine; 4-MeS-DMA
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	6–8 hours[1]
Identifiers
IUPAC name 1-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine
CAS Number	61638-07-1 Y
PubChem CID	143828
ChemSpider	126887 Y
UNII	C9ZVF4O01N
ChEMBL	ChEMBL447830 Y
CompTox Dashboard (EPA)	DTXSID80874362
Chemical and physical data
Formula	C12H19NO2S
Molar mass	241.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1(=C(C=C(C(=C1)SC)OC)CC(C)N)OC
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
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Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph's dose range as 5 to 10 mg orally and its duration as 6 to 8 hours.^[1] 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.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

Aleph is known to be a partial agonist of the serotonin 5-HT_2A receptor (EC₅₀Tooltip half-maximal effective concentration = 10–66 nM; E_maxTooltip maximal efficacy = 114–191%).^[2][3]

It has weak MAO-A inhibitory activity with an IC₅₀Tooltip half-maximal inhibitory concentration of 5.2 μM.^[4] For comparison, amphetamine has an IC₅₀ of 11 μM and 4-methylthioamphetamine (4-MTA) has a value of 0.2 μM.^[4]

Chemistry

Synthesis

The chemical synthesis of Aleph has been described.^[1]

Derivatives

Derivatives of Aleph include Aleph-2, Aleph-4, Aleph-6, and Aleph-7.^[1] 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.^[1]

History

Aleph was first tested by Alexander Shulgin in 1975.^[1] It was first described in the scientific literature by Shulgin and David E. Nichols in 1976.^[5][6] Its properties and effects in humans were described by them in 1978.^[7] Subsequently, the drug was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Names

Aleph was named by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet.^[1] Another earlier name of the drug is para-DOT.^[1][7]

Legal status

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.^[8]

See also

• DOx (psychedelics)
• 2C-T