2,5-Dimethoxy-4-ethylamphetamine

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2,5-Dimethoxy-4-ethylamphetamine
2,5-Dimethoxy-4-ethylamphetamine.svg
Systematic (IUPAC) name
1-(4-ethyl-2,5-dimethoxy-phenyl)propan-2-amine
Clinical data
Legal status Schedule I
Identifiers
CAS number 22004-32-6 N
ATC code ?
PubChem CID 27402
DrugBank DB01467
ChemSpider 25499 YesY
ChEMBL CHEMBL8224 YesY
Synonyms 2,5-dimethoxy-4-ethylamphetamine
Chemical data
Formula C13H21NO2 
Mol. mass 223.31 g/mol
 N (what is this?)  (verify)

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[edit]

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[edit]

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[edit]

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]

Legality[edit]

DOET is classified as a Schedule 1 substance in the United States, and is similarly controlled in other parts of the world. Internationally, DOET is a Schedule I drug under the Convention on Psychotropic Substances [1].

See also[edit]

References[edit]

  1. ^ a b Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5. 
  2. ^ "Articleid 50034244". Binding Database. Retrieved 29 April 2014. 
  3. ^ "Compound ID: CHEMBL2360469". ChEMBL. Retrieved 29 April 2014. 

External links[edit]