Aleph-7

Aleph-7
Clinical data
Other namesALEPH-7; DOT-7; 4-Propylthio-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-propylthioamphetamine; 4-PrS-DMA
Routes of
administration		Oral[1]
Drug classSerotonin 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 action15–30 hours[1]
Identifiers
  • 1-(2,5-dimethoxy-4-propylsulfanylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO2S
Molar mass269.40 g·mol−1
3D model (JSmol)
  • CCCSC1=C(C=C(C(=C1)OC)CC(C)N)OC
  • 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

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]

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-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 2.2 to 7.6 nM and an EmaxTooltip 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]

See also

References

  1. ^ a b c d e f g h i j Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal007.shtml
  2. ^ Pottie E, Poulie CB, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, Gloriam DE, Jensen AA, Kristensen JL, Stove CP (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci. 14 (15): 2727–2742. doi:10.1021/acschemneuro.3c00267. PMID 37474114.
  3. ^ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
  4. ^ Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE (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. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID 15801832.
  5. ^ Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
  6. ^ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
  7. ^ King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
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