Aleph, or Aleph-1, also known as DOT or para-DOT or as 4-methylthio-2,5-dimethoxyamphetamine, is a

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...

of the

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

and DOx families.

Effects

Aleph was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

, who named it after the first letter of the

Hebrew alphabet The Hebrew alphabet (, ), known variously by scholars as the Ktav Ashuri, Jewish script, square script and block script, is a unicase, unicameral abjad script used in the writing of the Hebrew language and other Jewish languages, most notably ...

. In his book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

'', Shulgin lists the dosage range as 5 to 10mg, with effects typically lasting for 6 to 8hours.

Pharmacology

Like many other psychedelics, Aleph is a

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

at the 5-HT_2A receptor ( EC₅₀ = 10 nM). It has weak MAO-A inhibitory activity with an IC₅₀ of 5.2 μM. For reference,

has an IC₅₀ of 11 μM and

4-methylthioamphetamine 4-Methylthioamphetamine (4-MTA), also known as ''para''-methylthioamphetamine (MTA), is a designer drug of the substituted amphetamine class developed in the 1990s by a team led by David E. Nichols, an American pharmacologist and medical chemist ...

has a value of 0.2 μM.

Homologues

Aleph-2

''Dosage'': 4–8 mg ''Duration'': 8–16 hours ''Effects'': Strong visuals '' 2C analog'':

2C-T-2 2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most ...

CAS number: 185562-00-9 SMILES: C1(=C(C=C(C(=C1)SCC)OC)CC(C)N)OC

Aleph-4

''Dosage'': 7–12 mg ''Duration'': 12–20 hours ''Effects'': "''profound and deep learning experiences''" -

'' 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

''Dosage'': 40 mg or more ''Duration'': very long, unspecified ''Effects'': enhances other psychoactive drugs, similar to

2C-D 2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, a ...

'' 2C analog'': 2C-T-6 (has never been synthesized) 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

''Dosage'': 4–7 mg ''Duration'': 15–30 hours '' 2C analog'':

2C-T-7 2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generall ...

CAS number: 207740-16-7 SMILES: C1(=C(C=C(C(=C1)SC4^4

Legal status

United States

In the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

, Aleph is a Schedule 1

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Sing ...

as a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

of 2C-T-4 and