Aleph (also known as DOT or 2,5-dimethoxy-4-methylthioamphetamine) is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science ...

hallucinogenic drug Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized ...

and a

substituted amphetamine Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with s ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace am ...

class of compounds, which can be used as an

entheogen Entheogens are psychoactive substances that induce alterations in perception, mood, consciousness, cognition, or behavior for the purposes of engendering spiritual development or otherwiseRätsch, Christian, ''The Encyclopedia of Psychoact ...

. It was first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamp ...

, who named it after the first letter of the

Hebrew alphabet The Hebrew alphabet ( he, אָלֶף־בֵּית עִבְרִי, ), known variously by scholars as the Ktav Ashuri, Jewish script, square script and block script, is an abjad script used in the writing of the Hebrew language and other Jewis ...

. In his book '' PiHKAL'', Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours. Like many other psychedelics, aleph is a

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonist ...

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,

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

has an IC₅₀ of 11 μM and

4-methylthioamphetamine 4-Methylthioamphetamine (4-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, at Purdue University. It acts as a non-neurotoxic h ...

has a value of 0.2 μM. A lower number indicates stronger inhibition.

Homologues

Aleph-2

''Dosage'': 7–12 mg ''Duration'': 8–16 hours ''Effects'': Strong visuals '' 2C analog'':

2C-T-2 2C-T-2 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 important psychedelic phenethylamine compounds. The drug ...

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 2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug. Chemistry 2C-T-4 is the 2-carbon homolog of al ...

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 (2,5-dimethoxy-4-methylphenethylamine or 2C-M) 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, and its activity wa ...

'' 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

Aleph-7

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

2C-T-7 2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic eff ...

CAS number: 207740-16-7 SMILES: C1(=C(C=C(C(=C1)SCCC)OC)CC(C)N)OC

Legality

In the United States Aleph is a Schedule 1 controlled substance as a positional isomer of

and

References

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
{{Phenethylamines Thioethers Substituted amphetamines Designer drugs 2,5-Dimethoxyphenethylamines