Aleph (psychedelic)

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{{nbsp}}mg, with effects typically lasting for 6 to 8{{nbsp}}hours.{{CitePiHKAL}}

Like many other psychedelics, Aleph is a partial agonist at the 5-HT_2A receptor (EC₅₀ = 10 nM).{{cite journal | vauthors = Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME | title = Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines | journal = Psychopharmacology | volume = 240 | issue = 1 | pages = 115–126 | date = January 2023 | pmid = 36477925 | pmc = 9816194 | doi = 10.1007/s00213-022-06279-2 }}{{cite journal | vauthors = Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME | title = Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines | journal = Psychopharmacology (Berl) | volume = 240 | issue = 1 | pages = 115–126 | date = January 2023 | pmid = 36477925 | pmc = 9816194 | doi = 10.1007/s00213-022-06279-2 | url = https://core.ac.uk/download/pdf/543784099.pdf}} 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.{{cite journal | vauthors = Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE | title = Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 7 | pages = 2407–2419 | date = April 2005 | pmid = 15801832 | doi = 10.1021/jm0493109 }}

{{Main|Aleph-2}}

Image:2,5-dimethoxy-4-ethylthioamphetamine.svg {{Clear|left}}

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

Image:Aleph-4.svg {{Clear|left}}

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

Image:Aleph-6.svg {{Clear|left}}

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|date=August 2023}}

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

Image:2,5-dimethoxy-4-propylthioamphetamine.svg {{Clear|left}}

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

In the United States, Aleph is a Schedule 1 controlled substance as a positional isomer of 2C-T-4 and 2C-T-7.{{cite web | title = Lists of: Scheduling Actions Controlled Substances Regulated Chemicals | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf | date = January 2023 | work = Drug and Chemical Evaluation Section, Diversion Control Division | publisher = Drug Enforcement Administration, U.S. Department of Justice }}

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

{{Reflist}}

• [http://www.erowid.org/library/books_online/pihkal/pihkal003.shtml Aleph Entry in PiHKAL]
• [https://isomerdesign.com/pihkal/read/pk/3 ALEPH Entry at PiHKAL·info]
• [http://www.erowid.org/library/books_online/pihkal/pihkal004.shtml Aleph-2 Entry in PiHKAL]
• [https://isomerdesign.com/pihkal/read/pk/4 ALEPH-2 Entry at PiHKAL·info]
• [http://www.erowid.org/library/books_online/pihkal/pihkal005.shtml Aleph-4 Entry in PiHKAL]
• [https://isomerdesign.com/pihkal/read/pk/5 ALEPH-4 Entry at PiHKAL·info]
• [http://www.erowid.org/library/books_online/pihkal/pihkal006.shtml Aleph-6 Entry in PiHKAL]
• [https://isomerdesign.com/pihkal/read/pk/6 ALEPH-6 Entry at PiHKAL·info]
• [http://www.erowid.org/library/books_online/pihkal/pihkal007.shtml Aleph-7 Entry in PiHKAL]
• [https://isomerdesign.com/pihkal/read/pk/7 ALEPH-7 Entry at PiHKAL·info]
• [https://tripsitter.com/amphetamines/aleph-6/ Aleph-6: Pharmacology, Side Effects, & Characteristics - Tripsitter]

{{Psychedelics}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

{{Chemical classes of psychoactive drugs}}

Category:Designer drugs

Category:DOx (psychedelics)

Category:Psychedelic phenethylamines

Category:Thioethers