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Aleph-2

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{{Infobox drug

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| image = 2,5-dimethoxy-4-ethylthioamphetamine.svg

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| routes_of_administration = Oral

| class = Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist

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| duration_of_action = 8–16{{nbsp}}hours

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| CAS_number = 185562-00-9

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| PubChem = 10264356

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| DrugBank = DB13940

| ChemSpiderID = 8439835

| UNII = Z1I419DRZZ

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| ChEMBL = 339611

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| synonyms = ALEPH-2; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-Ethylthio-2,5-dimethoxyamphetamine; DOT-2

| 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

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Aleph-2, or ALEPH-2, also known as 2,5-dimethoxy-4-ethylthioamphetamine, is a serotonergic psychedelic of the phenethylamine, amphetamine, and DOx families.{{cite book | vauthors = Shulgin T, Shulgin A | chapter = #4 ALEPH-2 2,5-DIMETHOXY-4-ETHYLTHIOAMPHETAMINE | pages = 464–467 | chapter-url = https://www.erowid.org/library/books_online/pihkal/pihkal004.shtml | title = PiHKAL: A Chemical Love Story | date = 1991 | publisher = Transform Press | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-0-9 | oclc = 25627628 | url = https://books.google.com/books?id=O8AdHBGybpcC }}{{cite book | vauthors = Shulgin A, Manning T, Daley PF | chapter = #4. ALEPH-2 | pages = 5 | chapter-url = https://archive.org/details/shulgin-index-vol-1/page/5/mode/1up | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher = Transform Press | location = Berkeley, CA | volume = 1 | year = 2011 | isbn = 978-0-9630096-3-0 | oclc = 709667010 }}

Use and effects

According to Alexander Shulgin, its dosage is 4 to 8{{nbsp}}mg orally and its duration is 8 to 16{{nbsp}}hours. The drug is said to produce strong visuals.

Pharmacology

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|+ {{Nowrap|Aleph-2 activities}}

TargetAffinity (Ki, nM)
5-HT1A1,674
5-HT1B2,037
5-HT1D1,532
5-HT1E3,088
5-HT1F{{Abbr|ND|No data}}
5-HT2A60.4 (Ki)
0.489–0.898 ({{Abbrlink|EC50|half-maximal effective concentration}})
104–108% ({{Abbrlink|Emax|maximal efficacy}})
5-HT2B1.6
5-HT2C50.3 (Ki)
0.0912–0.401 ({{Abbr|EC50|half-maximal effective concentration}})
105–114% ({{Abbr|Emax|maximal efficacy}})
5-HT3>10,000
5-HT4{{Abbr|ND|No data}}
5-HT5A>10,000
5-HT63,020
5-HT71,322
α1A>10,000
α1B>10,000
α1D{{Abbr|ND|No data}}
α2A5,803
α2B2,934
α2C1,388
β16,792
β226.1
β3{{Abbr|ND|No data}}
D1, D2>10,000
D3618.3
D4, D5>10,000
H1–H4>10,000
M1, M2>10,000
M31,907
M4>10,000
M58,018
I1319.8
σ1238.9
σ2>10,000
{{Abbrlink|TAAR1|Trace amine-associated receptor 1}}{{Abbr|ND|No data}}
{{Abbrlink|SERT|Serotonin transporter}}1,318 (Ki)
{{Abbrlink|NET|Norepinephrine transporter}}>10,000 (Ki)
{{Abbrlink|DAT|Dopamine transporter}}>10,000 (Ki)
{{Abbrlink|MAO-A|Monoamine oxidase A}}3,200–3,800 ({{Abbr|IC50|half-maximal inhibitory concentration}}) (rat)
{{Abbrlink|MAO-B|Monoamine oxidase B}}>100,000 ({{Abbr|IC50|half-maximal inhibitory concentration}}) (rat)
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| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: {{cite web | title=Kᵢ Database | website=PDSP | date=1 April 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12945&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=1 April 2025}}{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM50164337 2-(4-Ethylsulfanyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::CHEMBL339611 | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50164337 | access-date=1 April 2025}}{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | pages = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free }}{{cite journal | vauthors = Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M | title = Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships | journal = Biochem Pharmacol | volume = 54 | issue = 12 | pages = 1361–1369 | date = December 1997 | pmid = 9393679 | doi = 10.1016/s0006-2952(97)00405-x | url = https://mrtoasted.com/~vaaguh/maoi-properties-of-methoxylated-and-alkylthioamp-derivates.pdf}}{{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 = J Med Chem | volume = 48 | issue = 7 | pages = 2407–2419 | date = April 2005 | pmid = 15801832 | doi = 10.1021/jm0493109 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=61e1af109f88d1c41da1f218f9403dff12b5d98d| url-access = subscription }}

Aleph-2 acts as a serotonin 5-HT2 receptor agonist.{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R }} The drug is also a weak monoamine oxidase inhibitor (MAOI), with {{Abbrlink|IC50|half-maximal inhibitory concentration}} values of 3,200{{nbsp}}nM for monoamine oxidase A (MAO-A) and >100,000{{nbsp}}nM for monoamine oxidase B (MAO-B). Aleph-2 produces anxiolytic effects in rodents.{{cite journal | vauthors = Acuña-Castillo C, Scorza C, Reyes-Parada M, Cassels BK, Huidobro-Toro JP | title = ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2a and 5-HT2c receptor agonist | journal = Life Sciences | volume = 67 | issue = 26 | pages = 3241–3247 | date = November 2000 | pmid = 11191631 | doi = 10.1016/s0024-3205(00)00906-1 }}{{cite journal | vauthors = Scorza MC, Reyes-Parada M, Silveira R, Viola H, Medina JH, Viana MB, Zangrossi H, Graeff FG | title = Behavioral effects of the putative anxiolytic (+/-)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice | journal = Pharmacology, Biochemistry, and Behavior | volume = 54 | issue = 2 | pages = 355–361 | date = June 1996 | pmid = 8743595 | doi = 10.1016/0091-3057(95)02149-3 }}{{cite journal | vauthors = Reyes-Parada M, Scorza C, Romero V, Silveira R, Medina JH, Andrus D, Nichols DE, Cassels BK | title = (+/-)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 354 | issue = 5 | pages = 579–585 | date = November 1996 | pmid = 8938655 | doi = 10.1007/BF00170831 }}

See also

References

{{Reflist}}

External links

  • [https://isomerdesign.com/pihkal/explore/4 ALEPH-2 - Isomer Design]
  • [https://www.erowid.org/library/books_online/pihkal/pihkal004.shtml ALEPH-2 - PiHKAL - Erowid]
  • [https://isomerdesign.com/pihkal/read/pk/4 ALEPH-2 - PiHKAL - Isomer Design]

{{Psychedelics}}

{{Serotonin receptor modulators}}

{{Monoamine metabolism modulators}}

{{Phenethylamines}}

Category:5-HT2A agonists

Category:5-HT2C agonists

Category:Anxiolytics

Category:Designer drugs

Category:DOx (psychedelics)

Category:Monoamine oxidase inhibitors

Category:Psychedelic phenethylamines

Category:Thioethers