Aleph (psychedelic)

Aleph, or Aleph-1, also known as 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; 2,5-Dimethoxy-4-methylthioamphetamine; 4-Methylthio-2,5-dimethoxyamphetamine
Routes of administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
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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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 dosage range as 5 to 10 mg, with effects typically lasting for 6 to 8 hours.^[1]

Pharmacology

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]

Homologues

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

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