α-Ethyltryptamine

α-Ethyltryptamine
INN: Etryptamine
Clinical data
Trade namesMonase[1]
Other namesalpha-Ethyltryptamine; αET; AET; α-ET; Etryptamine; PAL-125;[2] 3-(2-Aminobutyl)indole; 3-Indolylbutylamine; U-17312E; U17312E; Ro 3-1932; NSC-63963; NSC-88061, Etryptamine (USAN US)
Routes of
administration		Oral[1]
Drug classEntactogen; Stimulant; Monoamine releasing agent; Serotonin receptor agonist; Monoamine oxidase inhibitor[1]
ATC code
  • None
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)[3]
  • CA: Schedule III
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
  • UN: Psychotropic Schedule I
Pharmacokinetic data
MetabolismHydroxylation[4]
Metabolites• 6-Hydroxy-αET (inactive)[1][4]
Onset of action0.5–1.5 hours[4]
Elimination half-life~8 hours[4]
Duration of action6–8 hours (100–150 mg)[5][4]
ExcretionUrine (majority)[4]
Identifiers
IUPAC name
  • 1-(1H-indol-3-yl)butan-2-amine
CAS Number
PubChem CID
PubChem SID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
Melting point222 to 223 °C (432 to 433 °F)
SMILES
  • CCC(N)CC1=CNC2=CC=CC=C12
InChI
  • InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3 Y
  • Key:ZXUMUPVQYAFTLF-UHFFFAOYSA-N Y
  (verify)

α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family.[1][5][6] It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.[1][5][7]

Side effects of αET include facial flushing, headache, gastrointestinal distress, insomnia, irritability, appetite loss, and sedation, among others.[4] A rare side effect of αET is agranulocytosis.[1][6][8] αET acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a weak serotonin receptor agonist, and as a weak monoamine oxidase inhibitor.[1][5][2] It may also produce serotonergic neurotoxicity.[1][5][9] αET is a substituted tryptamine and is closely related to α-methyltryptamine (αMT) and other α-alkylated tryptamines.[1][5]

αET was first described in 1947.[1][10] It was used as an antidepressant for about a year around 1961.[1] The drug started being used recreationally in the 1980s and several deaths have been reported.[1][5][11][4] αET is a controlled substance in various countries, including the United States and United Kingdom.[1][11] There has been renewed interest in αET, for instance as an alternative to MDMA, with the development of psychedelics and entactogens as medicines in the 2020s.[1][5]

  1. ^ a b c d e f g h i j k l m n o Glennon RA, Dukat MG (December 2023). "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacology & Translational Science. 6 (12): 1780–1789. doi:10.1021/acsptsci.3c00139. PMC 10714429. PMID 38093842.
  2. ^ a b Cite error: The named reference BloughLandavazo2014 was invoked but never defined (see the help page).
  3. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  4. ^ a b c d e f g h Cite error: The named reference Barceloux2012 was invoked but never defined (see the help page).
  5. ^ a b c d e f g h Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". Journal of Psychopharmacology. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  6. ^ a b Shulgin A, Shulgin A (1997). ""Part 2, The Chemistry Continues: #11, a-ET: Alpha-Ethyltryptamine; Indole,3-(2-Aminobutyl); Tryptamine,Alpha-Ethyl; 3-(2-Aminobutyl)Indole; Monase," part v, "EXTENSIONS AND COMMENTARY."" (Book). Tryptamines i Have Known and Loved: The Continuation, (First ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. Retrieved 15 November 2013. This base, a-ET or etryptamine, was a promising anti-depressant, explored clinically as the acetate salt by Upjohn under the name of Monase. Its central stimulant activity is probably not due to its monoamineoxidase inhibition activity, but appears to stem from its structural relationship to the indolic psychedelics. It was withdrawn from potential commercial use with the appearance of an unacceptable incidence of a medical condition known as agranulocytosis, but the extra mural research into its action, among the lay population, goes on, [...]
  7. ^ US Patent 3296072, Szmuszkovicz J, "Method of Treating Mental Depression", published 1967-01-03, issued 1967-01-03, assigned to Upjohn Company. 
  8. ^ Burtin JW (August 1962). "Agranulocytosis following Monase therapy". J Kans Med Soc. 63: 338–340. PMID 13875179.
  9. ^ Cite error: The named reference HuangJohnsonNichols1991 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference SnyderKatz1947 was invoked but never defined (see the help page).
  11. ^ a b Cite error: The named reference VarìPichiniGiorgetti2019 was invoked but never defined (see the help page).
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