Α-Ethyltryptamine
Chemical compound
α-Ethyltryptamine (αET , AET ), also known as etryptamine (INN , BAN , USAN ), is a psychedelic , stimulant , and entactogenic drug of the tryptamine class.[2] [3] It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.[4]
History
Originally believed to exert its effects predominantly via monoamine oxidase inhibition , α-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during the 1960s as an antidepressant by Upjohn chemical company in the United States under the name Monase , but was withdrawn from potential commercial use due to incidence of idiosyncratic agranulocytosis .[5]
α-Ethyltryptamine 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
α-Ethyltryptamine is structurally and pharmacologically related to αMT, α-methyltryptamine , and it is believed[5] 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, α-ethyltryptamine is less stimulating and hallucinogenic , its effects resembling more those of entactogens like MDMA ("Ecstasy").
Similarly to αMT, α-ethyltryptamine is a releasing agent of serotonin , norepinephrine and dopamine , with serotonin being the primary neurotransmitter affected.[6] In addition, it acts as a non-selective serotonin receptor agonist .[citation needed ] A study performed in 1991[7] with rat subjects provided evidence that α-ethyltryptamine may induce serotonergic neurotoxicity similar to that of MDMA . As with many other serotonin releasing agents , injury can occur when excessive doses are taken or when combined with drugs such as other MAOIs .[8]
References
^ 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 .
^ " "Erowid AET (alpha-ethyltryptamine) Vault" " .
^ 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 .
^ US Patent 3296072 , Szmuszkovicz Jacob, "Method of Treating Mental Depression ", published 1967-01-03, assigned to Upjohn Co
^ 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, (1st. ed.). Berkeley, CA : Transform Press, ©1997. 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,
^ Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers" . Bioorganic & Medicinal Chemistry Letters . 24 (19): 4754–4758. doi :10.1016/j.bmcl.2014.07.062 . PMC 4211607 . PMID 25193229 .
^ 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 .
^ Gillman PK (October 2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity" . British Journal of Anaesthesia . 95 (4): 434–441. doi :10.1093/bja/aei210 . PMID 16051647 . "Drugs such as MDMA, ecstasy (3,4-methylenedioxymethamphetamine), if combined with MAOIs (including moclobemide) do also cause fatalities because they act as serotonin releasers, "
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4,5-MDO-DiPT
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4-AcO-DMT
4-AcO-DiPT
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4-Me-αMT
4-MeO-DiPT
4-MeO-DMT
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5,6-MDO-DMT
5,6-MDO-MiPT
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5-HTP
5-iPrO-AMT
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5-MeO-pyr-T
5-MeO-NBpBrT
5-Methyl-DMT
5-(Nonyloxy)tryptamine
6-Fluoro-αMT
6-Fluoro-DMT
6-Hydroxymelatonin
6-MeO-THH
7-Chloro-AMT
7-Methyl-α-ethyltryptamine
7-Methyl-DMT
Acetryptine
Aeruginascin
αET
Alpha,N-DMT
α,N,N-Trimethyltryptamine
Alpha,N,O-TMS
AL-37350A
αMT
Baeocystin
BNC-210
Bufotenidine
Bufotenin (5-HO-DMT)
BW-723C86
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DPT
E-6801
E-6837
Ethocybin
EiPT
EMDT
EPT
FGIN-127
FGIN-143
Harmaline
HIOC
Ibogaine
Idalopirdine
Indorenate
Iprocin
Lespedamine
Luzindole
MET
Methylbutyltryptamine
MiPT
MPT
Miprocin
Melatonin
MPMI
MS-245
NAS
N-Ethyltryptamine
N-Feruloylserotonin
NMT
DMT
Norbaeocystin
Normelatonin
N-t-Butyltryptamine
O-4310
Oxypertine
Plakohypaphorine
PiPT
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
Rizatriptan
RU-28306
Serotonin
ST-1936
Sumatriptan
Tryptamine
Tryptophan
Yohimbine
Yuremamine
Zolmitriptan