alpha-Ethyltryptamine

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α-Ethyltryptamine
AET.svg
Alpha-Ethyltryptamine-3d-sticks.png
Systematic (IUPAC) name
1-(1H-indol-3-yl)butan-2-amine
Clinical data
Legal status
Identifiers
CAS number 2235-90-7 YesY 118-68-3
ATC code None
PubChem CID 8367
DrugBank DB01546
ChemSpider 8064 YesY
Synonyms 3-(2-aminobutyl)indole
Chemical data
Formula C12H16N2 
Mol. mass 188.27 g/mol
Physical data
Melt. point 222–223 °C (432–433 °F)
 YesY (what is this?)  (verify)

α-Ethyltryptamine (α-ET, AET, Monase, or etryptamine) is a psychedelic, stimulant, and entactogenic drug of the tryptamine class.[1] [2] It was originally developed as an antidepressant by workers at Upjohn in the 1960s. [3]

History[edit]

Originally believed to exert its effects predominantly via monoamine oxidase inhibition, alpha-ethyltryptamine was developed during the 1960s as an antidepressant by Upjohn chemical company in the United States under the name Monase, but was withdrawn from potential commercial use due to an unacceptable incidence of idiosyncratic agranulocytosis.[4]

α-ET gained limited recreational popularity as a designer drug in the 1980s. Subsequently, in the USA it was added to the Schedule I list of illegal substances in 1993.

Pharmacology[edit]

αET is structurally and pharmacologically related to αMT, α-methyltryptamine, and it is believed[4] its central stimulant activity is probably not due to its activity as an MAOI, but appears to stem from its structural relationship to the indolic psychedelics. In contrast to αMT, αET is less stimulating and hallucinogenic, its effects resembling more those of entactogens like MDMA ("Ecstasy").

Similarly to α-MT, α-ET is a releasing agent of serotonin, norepinephrine and dopamine (with serotonin being the primary neurotransmitter affected); in addition, it acts as a non-selective serotonin receptor agonist.[citation needed] A study performed in 1991[5] with rat subjects provided evidence that a-ET may induce serotonin neurotoxicity similar to that of Ecstasy. As with many other serotonin releasing agents, injury can occur when excessive doses are taken or when combined with drugs such as other MAOIs.[6]

See also[edit]

References[edit]

  1. ^ ""Erowid AET (alpha-ethyltryptamine) Vault".". 
  2. ^ Alexander Shulgin; Ann Shulgin. ""#11, a-ET: Alpha-Ethyltryptamine; Indole,3-(2-Aminobutyl); Tryptamine,Alpha-Ethyl; 3-(2-Aminobutyl)Indole; Monase,"". "Tryptamines i Have Known And Loved: The Continuation", Part 2, "The Chemistry Continues". Erowid Online Library. p. 11. Retrieved 15 November 2013. 
  3. ^ US Patent 3296072, Szmuszkovicz Jacob, "Method of Treating Mental Depression", published 1967-01-03, assigned to Upjohn Co 
  4. ^ a b Alexander Shulgin; Ann Shulgin (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, (in English) (1st. ed.). Berkeley, CA : Transform Press, ©1997. ISBN 0-9630096-9-9. 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,"" 
  5. ^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology 200 (1): 187–190. doi:10.1016/0014-2999(91)90686-K. PMID 1722753. 
  6. ^ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia 95 (4): 434–441. doi:10.1093/bja/aei210. PMID 16051647.  edit "Drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers,"

External links[edit]