2,5-Dimethoxy-4-ethylamphetamine

2,5-Dimethoxy-4-ethylamphetamine
Clinical data
Other namesDOET; DOEt; DOE; HECATE; Hecate; DMEA; 2,5-Dimethoxy-4-ethylamphetamine; 4-Ethyl-2,5-dimethoxyamphetamine; Dimethoxyethylamphetamine; Ethyldimethoxyamphetamine
Drug classSerotonergic psychedelic; Serotonin 5-HT2 receptor agonist; Antidepressant; Psychic energizer; Cognitive enhancer
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)[1]
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
  • UN: Psychotropic Schedule I
Pharmacokinetic data
MetabolismOxidation of the 4-position ethyl group[2][7]
Onset of action1–3 hours[2][3][4][5]
Duration of action5–20 hours[4][6]
ExcretionUrine (10–40% unchanged within 24 hours)[2][3][4]
Identifiers
IUPAC name
  • 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO2
Molar mass223.316 g·mol−1
3D model (JSmol)
SMILES
  • O(c1cc(c(OC)cc1CC(N)C)CC)C
InChI
  • InChI=1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3 Y
  • Key:HXJKWPGVENNMCC-UHFFFAOYSA-N Y
  (verify)

2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.[8][6][3][2] It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline.[2][9] The drug acts as a selective agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[10][11]

DOET was first discovered by Alexander Shulgin in the 1960s.[12] It was clinically studied at low and sub-hallucinogenic doses for potential use as a pharmaceutical drug acting as a "psychic energizer" by Dow Chemical Company in the 1960s.[12] However, its development was terminated after DOM emerged as a street drug and caused a public health crisis in San Francisco in 1967.[12][13] Nonetheless, DOET's effects at low doses were extensively characterized in small clinical trials.[2][4][14][15][5] The psychedelic effects of DOET at higher doses were subsequently described by Shulgin in his book PiHKAL in 1991.[6]

DOET is taken by mouth.[6][3][4] It has a slow onset of 1 to 3 hours, a delayed peak of 3 to 5 hours, and a dose-dependent and potentially very long duration of 5 to 20 hours.[6][16][2][3] Effects at low doses include mild euphoria, enhanced self-awareness, and talkativeness, among others.[2][3][4] Mild closed-eye visuals can also occur.[15][5] At higher doses, DOET produces psychedelic effects including heightened emotions, sensory enhancement, rich closed-eye visuals, and open-eye visuals, among others.[6][5] Physical effects include pupil dilation, increased heart rate, and increased blood pressure.[4][14][17]

  1. ^ 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.
  2. ^ a b c d e f g h Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
  3. ^ a b c d e f Wills B, Erickson T (9 March 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". In Barceloux DG (ed.). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 156–192. doi:10.1002/9781118105955.ch10. ISBN 978-0-471-72760-6.
  4. ^ a b c d e f g Cite error: The named reference SnyderFaillaceWeingartner1968 was invoked but never defined (see the help page).
  5. ^ a b c d Cite error: The named reference SnyderUngerBlatchley1974 was invoked but never defined (see the help page).
  6. ^ a b c d e f Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5.
  7. ^ Cite error: The named reference TanseyEstevezHo1975 was invoked but never defined (see the help page).
  8. ^ Shulgin A, Manning T, Daley PF (2011). "#56. DOET (2,5-Dimethoxy-4-ethylamphetamine)". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. pp. 106–110. ISBN 978-0-9630096-3-0.
  9. ^ Cite error: The named reference HassanBoschSingh2017 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference LuethiRudinHoener2022 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Ray2010 was invoked but never defined (see the help page).
  12. ^ a b c Baggott MJ (1 October 2023). "Learning about STP: A Forgotten Psychedelic from the Summer of Love" (PDF). History of Pharmacy and Pharmaceuticals. 65 (1): 93–116. doi:10.3368/hopp.65.1.93. ISSN 2694-3034. Retrieved 26 January 2025.
  13. ^ Cite error: The named reference TroutDaley2024 was invoked but never defined (see the help page).
  14. ^ a b Cite error: The named reference SnyderFaillace1969 was invoked but never defined (see the help page).
  15. ^ a b Cite error: The named reference SnyderWeingartnerFaillace1971 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Bonson2005 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference WeingartnerSnyderFaillace1970 was invoked but never defined (see the help page).
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.