Aleph-7

Aleph-7, or ALEPH-7, also known as 4-propylthio-2,5-dimethoxyamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.^[1] It is one of the Aleph series of compounds.^[1]

Other namesALEPH-7; DOT-7; 4-Propylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-propylthioamphetamine; 4-PrS-DMA

Routes of
administrationOral^[1]

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Monoamine oxidase inhibitor; Reversible inhibitor of MAO-A

ATC code

• None

Quick facts Clinical data, Other names ...

Aleph-7

Clinical data
Other names	ALEPH-7; DOT-7; 4-Propylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-propylthioamphetamine; 4-PrS-DMA
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Monoamine oxidase inhibitor; Reversible inhibitor of MAO-A
ATC code	None
Pharmacokinetic data
Duration of action	15–30 hours[1]
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-propylsulfanylphenyl)propan-2-amine
CAS Number	207740-16-7
PubChem CID	11197521
ChemSpider	9372590
UNII	RB42O7HM6C
ChEMBL	ChEMBL341318
CompTox Dashboard (EPA)	DTXSID901043214
Chemical and physical data
Formula	C14H23NO2S
Molar mass	269.40 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCSC1=C(C=C(C(=C1)OC)CC(C)N)OC
InChI InChI=1S/C14H23NO2S/c1-5-6-18-14-9-12(16-3)11(7-10(2)15)8-13(14)17-4/h8-10H,5-7,15H2,1-4H3 Key:XHWDHFUBCVWXDZ-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Aleph-7's dose as 4 to 7 mg orally and its duration as 15 to 30 hours.^[1] The effects of Aleph-7 have been reported to include strangeness, slight visual changes, intense but difficult to describe altered states of consciousness, everything feeling "preprogrammed", emotional changes, negative reactions, unwillingness to take the drug again, relaxation, and paresthesia, among others.^[1] It was said to produce a "Beth state", defined as a state of uncaring, anhedonia, and emotionlesssness.^[1] Many other drugs are also said to have a touch of such a state, but Aleph-7 to have more of it than most.^[1]

It is a potent agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 2.2 to 7.6 nM and an E_maxTooltip maximal efficacy of 116 to 189%.^[2] The drug is also a weak monoamine oxidase inhibitor (MAOI), specifically a reversible inhibitor of MAO-A (RIMA), with an IC₅₀Tooltip half-maximal inhibitory concentration of 2.4 μM.^[3][4]

The chemical synthesis of Aleph-7 has been described.^[1]

Aleph-7 was first described in the scientific literature by Shulgin in 1981.^[5][6] Subsequently, it was described in greater detail by Shulgin PiHKAL in 1991.^[1] The drug was encountered as a novel designer drug in Europe in 2005.^[7] It is a controlled substance in Canada under phenethylamine blanket-ban language.^[8]