Aleph-2

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title: "Aleph-2" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["5-ht2a-agonists", "5-ht2c-agonists", "anxiolytics", "designer-drugs", "dox-(psychedelics)", "ethylthio-compounds", "monoamine-oxidase-inhibitors", "pihkal", "psychedelic-phenethylamines"] topic_path: "general/5-ht2a-agonists" source: "https://en.wikipedia.org/wiki/Aleph-2" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::data[format=table title="Infobox drug"]

Field	Value
image	Aleph-2.svg
image_class	skin-invert-image
width	250px
routes_of_administration	Oral
class	Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist
ATC_prefix	None
duration_of_action	8–16hours
CAS_number	185562-00-9
PubChem	10264356
DrugBank	DB13940
ChemSpiderID	8439835
UNII	Z1I419DRZZ
ChEMBL	339611
synonyms	ALEPH-2; DOT-2; 4-Ethylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-EtS-DMA
IUPAC_name	1-(4-ethylsulfanyl-2,5-dimethoxyphenyl)propan-2-amine
C	13
SMILES	CCSC1=C(C=C(C(=C1)OC)CC(C)N)OC
StdInChI	1S/C13H21NO2S/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3
StdInChIKey	MCYCODJKXUJSAT-UHFFFAOYSA-N
::

| drug_name = | image = Aleph-2.svg | image_class = skin-invert-image | width = 250px | caption =

| pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral | class = Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist | ATC_prefix = None | ATC_suffix =

| legal_status =

| bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = 8–16hours | excretion =

| CAS_number = 185562-00-9 | CAS_supplemental = | PubChem = 10264356 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = DB13940 | ChemSpiderID = 8439835 | UNII = Z1I419DRZZ | KEGG = | ChEBI = | ChEMBL = 339611 | NIAID_ChemDB = | PDB_ligand = | synonyms = ALEPH-2; DOT-2; 4-Ethylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-EtS-DMA

| IUPAC_name = 1-(4-ethylsulfanyl-2,5-dimethoxyphenyl)propan-2-amine | C=13 | H=21 | N=1 | O=2 | S=1 | SMILES = CCSC1=C(C=C(C(=C1)OC)CC(C)N)OC | StdInChI = 1S/C13H21NO2S/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 | StdInChIKey = MCYCODJKXUJSAT-UHFFFAOYSA-N

Aleph-2, or ALEPH-2, also known as 4-ethylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is one of the Aleph series of compounds. The drug was encountered as a novel designer drug in Europe in 2023.

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph-2's dose as 4 to 8mg orally and its duration as 8 to 16hours. The effects of Aleph-2 have been reported to include "almost no visual phenomena" to "extraordinary visuals and interpretations", visual distortion and movement, enhanced auditory and tactile perception, and a sensation of physical warmth, and residual shakiness and muscle tremors, among others. There is an unpredictability with the dosing and effects of Aleph-2, such that one person who took 4mg had strong effects including ending up in a fetal position, in relative hibernation for several hours, and with substantial amnesia, whereas another person who took 8mg experienced only a bare threshold including slight lightheadedness.

Interactions

Pharmacology

Pharmacodynamics

::data[format=table title="{{Nowrap|Aleph-2 activities}}"]

Target	Affinity (Ki, nM)
5-HT1A	1,674
5-HT1B	2,037
5-HT1D	1,532
5-HT1E	3,088
5-HT1F	ND
5-HT2A	60.4 (Ki)
0.489–0.898 ()
104–108% ()
5-HT2B	1.6
5-HT2C	50.3 (Ki)
0.0912–0.401 (EC50)
105–114% (Emax)
5-HT3	10,000
5-HT4	ND
5-HT5A	10,000
5-HT6	3,020
5-HT7	1,322
α1A	10,000
α1B	10,000
α1D	ND
α2A	5,803
α2B	2,934
α2C	1,388
β1	6,792
β2	26.1
β3	ND
D1, D2	10,000
D3	618.3
D4, D5	10,000
H1–H4	10,000
M1, M2	10,000
M3	1,907
M4	10,000
M5	8,018
I1	319.8
σ1	238.9
σ2	10,000
	ND
	1,318 (Ki)
	10,000 (Ki)
	10,000 (Ki)
	3,200–3,800 (IC50) (rat)
	100,000 (IC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:
::

Aleph-2 acts as a serotonin 5-HT2 receptor agonist. The drug is also a weak monoamine oxidase inhibitor (MAOI), with values of 3,200nM for monoamine oxidase A (MAO-A) and 100,000nM for monoamine oxidase B (MAO-B). Aleph-2 produces anxiolytic effects in rodents.

Chemistry

Synthesis

The chemical synthesis of Aleph-2 has been described.

Analogues

Analogues of Aleph-2 include Aleph, Aleph-4, Aleph-6, Aleph-7, and 2C-T-2, among others.

History

Aleph-2 was first described in the scientific literature by Alexander Shulgin in 1978. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Aleph-2 was encountered as a novel designer drug in Europe in 2023.

Society and culture

Legal status

Canada

Aleph-2 is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

Aleph-2 is not an explicitly controlled substance in the United States. However, it is a Schedule I controlled substance in this country as an isomer of 2C-T-4.

References

References

1. (1991). "PiHKAL: A Chemical Love Story". Transform Press.
2. (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". Transform Press.
3. (1 May 1996). "ALEPH-2".
4. (1 April 2025). "Kᵢ Database".
5. "BDBM50164337 2-(4-Ethylsulfanyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL339611". BindingDB.
6. (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol.
7. (December 1997). "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships". Biochem Pharmacol.
8. (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". J Med Chem.
9. (February 2010). "Psychedelics and the human receptorome". PLOS ONE.
10. (November 2000). "ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2a and 5-HT2c receptor agonist". Life Sciences.
11. (June 1996). "Behavioral effects of the putative anxiolytic (+/-)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice". Pharmacology, Biochemistry, and Behavior.
12. (November 1996). "(+/-)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology.
13. (1978). "Stimulants". Springer US.
14. (1978). "QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens". National Institute on Drug Abuse.
15. (1980). "Burger's Medicinal Chemistry". Wiley.
16. (1982). "Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs". Springer Berlin Heidelberg.
17. "Controlled Drugs and Substances Act".
18. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
19. [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".

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