Chemistry:2,5-Dimethoxy-4-ethylamphetamine

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Short description: Psychedelic drug
2,5-Dimethoxy-4-ethylamphetamine
2,5-Dimethoxy-4-ethylamphetamine.svg
Clinical data
Other names2,5-dimethoxy-4-ethylamphetamine
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC13H21NO2
Molar mass223.316 g·mol−1
3D model (JSmol)
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2,5-Dimethoxy-4-ethylamphetamine (DOET, DOE, Hecate) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved).[1]

Chemistry

DOET is in a class of compounds commonly known as substituted amphetamines; its full chemical name is 4-ethyl-2,5-dimethoxy-alpha-methylbenzeneethanamine, or 1-(2,5-dimethoxy-4-ethylphenyl)propan-2-amine. It has an active stereocenter and (R)-DOET is the more active enantiomer. DOET is an extremely rare compound and reports of its effects and toxicology in humans are sparse. However, like the more common 2,5-dimethoxy-amphetamine analogues DOB, DOI and DOM, it is a potent and long-acting psychedelic. Removal of the alpha-methyl moiety yields the 2-carbon analogue, commonly known as 2C-E, another psychedelic compound first synthesized by Dr. Alexander Shulgin.

Pharmacology

Similarly to related drugs like DOM, DOET likely acts as a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist.[citation needed] It is an agonist of human TAAR1.[2][3]

Effects

DOET produces psychedelic effects that last up 14–20 hours. In PiHKAL, Shulgin lists the dosage of DOET as being 2–7 mg orally, with 6–7 mg being the dosage for full, desired effects.[1]

Legal status

Internationally, DOET is a Schedule I controlled drug; under the Convention on Psychotropic Substances, it's legal only for medical uses or scientific research:[1].

United States

DOET is classified as a Schedule I substance in the United States and is similarly controlled in other parts of the world.

Australia

DOET is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[4] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[4]

See also

  • 2,5-Dimethoxy-4-Substituted Amphetamines

References

  1. ↑ 1.0 1.1 PiHKAL: A Chemical Love Story. United States: Transform Press. September 1991. pp. 978. ISBN 0-9630096-0-5. https://erowid.org/library/books_online/pihkal/pihkal066.shtml. 
  2. ↑ "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorganic & Medicinal Chemistry 19 (23): 7044–7048. December 2011. doi:10.1016/j.bmc.2011.10.007. PMID 22037049. 
  3. ↑ "Compound ID: CHEMBL2360469". ChEMBL. https://www.ebi.ac.uk/chembl/compound/inspect/CHEMBL2360469. 
  4. ↑ 4.0 4.1 "Poisons Standard". Therapeutics Goods Administration. Australian Government. October 2015. https://www.comlaw.gov.au/Details/F2015L01534. 

External links



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