Aleph-2

Aleph-2, or ALEPH-2, also known as 4-ethylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.^[1][2][3] It is one of the Aleph series of compounds.^[1]

Aleph-2

Clinical data
Other names	ALEPH-2; DOT-2; 4-Ethylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-ethylthioamphetamine; 4-EtS-DMA
Routes of administration	Oral[1][2]
Drug class	Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2 receptor agonist
ATC code	None
Pharmacokinetic data
Duration of action	8–16 hours[1][2]
Identifiers
IUPAC name 1-(4-ethylsulfanyl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number	185562-00-9
PubChem CID	10264356
DrugBank	DB13940
ChemSpider	8439835
UNII	Z1I419DRZZ
ChEMBL	ChEMBL339611
CompTox Dashboard (EPA)	DTXSID401043188
Chemical and physical data
Formula	C13H21NO2S
Molar mass	255.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCSC1=C(C=C(C(=C1)OC)CC(C)N)OC
InChI InChI=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 Key:MCYCODJKXUJSAT-UHFFFAOYSA-N

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph-2's dose as 4 to 8 mg orally and its duration as 8 to 16 hours.^[1][2] 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.^[1][2] There is an unpredictability with the dosing and effects of Aleph-2, such that one person who took 4 mg 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 8 mg experienced only a bare threshold including slight lightheadedness.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

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 (EC50Tooltip half-maximal effective concentration) 104–108% (EmaxTooltip maximal efficacy)
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
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	1,318 (Ki)
NETTooltip Norepinephrine transporter	>10,000 (Ki)
DATTooltip Dopamine transporter	>10,000 (Ki)
MAO-ATooltip Monoamine oxidase A	3,200–3,800 (IC50) (rat)
MAO-BTooltip Monoamine oxidase B	>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: [4][5][3][6][7][8]

Aleph-2 acts as a serotonin 5-HT₂ receptor agonist.^[3][9] The drug is also a weak monoamine oxidase inhibitor (MAOI), with IC₅₀Tooltip half-maximal inhibitory concentration values of 3,200 nM for monoamine oxidase A (MAO-A) and >100,000 nM for monoamine oxidase B (MAO-B).^[6][7] Aleph-2 produces anxiolytic effects in rodents.^[9][10][11]

Chemistry

Synthesis

The chemical synthesis of Aleph-2 has been described.^[1][2]

Analogues

Analogues of Aleph-2 include Aleph, Aleph-4, Aleph-6, Aleph-7, and 2C-T-2, among others.^[1][2]

History

Aleph-2 was first described in the scientific literature by Alexander Shulgin in 1978.^{[12][13][14][15]} Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Legal status

United States

Aleph-2 is not a controlled substance in the United States as of 2011.^[2]

See also

• DOx (psychedelics)
• Aleph (psychedelics)
• 2C-T-2