Aleph (psychedelic)

Aleph, or Aleph-1, also known as DOT or para-DOT or as 4-methylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the amphetamine and DOx families.^[1]

Aleph

Clinical data
Other names	Aleph; Aleph-1; ALEPH; ALEPH-1; DOT; DOT-1; Para-DOT; 2,5-Dimethoxy-4-methylthioamphetamine; 4-Methylthio-2,5-dimethoxyamphetamine
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Onset 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

Aleph was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dose range as 5 to 10 mg orally, with effects typically lasting for 6 to 8 hours.^[1]

Interactions

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

Pharmacology

Pharmacodynamics

Like many other psychedelics, Aleph is a partial agonist at the 5-HT_2A receptor (EC₅₀ = 10 nM).^[2][3] 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.^[4]

List of Aleph drugs

Aleph-2

Main article: Aleph-2

Aleph-2

Dosage: 4–8 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)^{[citation needed]}

CAS number: 952006-44-9

SMILES: C1(=C(C=C(C(=C1)SC2=CC=CC=C2)OC)CC(C)N)OC=DSC4 R=5SC4_5⁶

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)SC4^4

Society and culture

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.^[5]

See also

• 2,5-Dimethoxy-4-substituted amphetamines (DOx)
• Substituted methoxyphenethylamine