2,5-Dimethoxy-4-ethylamphetamine

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2,5-Dimethoxy-4-ethylamphetamine
2,5-Dimethoxy-4-ethylamphetamine.svg
Legal status
Legal status
Identifiers
CAS Number 22004-32-6 N
PubChem CID 27402
DrugBank DB01467 YesY
ChemSpider 25499 YesY
ChEMBL CHEMBL8224 YesY
Synonyms 2,5-dimethoxy-4-ethylamphetamine
Chemical and physical data
Systematic (IUPAC) name: 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine
3D model (Jmol) Interactive image
Formula C13H21NO2
Molar mass 223.31 g/mol
 NYesY (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]

Legal Status[edit]

Internationally, DOET is a Schedule I controlled drug under the Convention on Psychotropic Substances [1].

United States[edit]

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

Australia[edit]

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[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. 
  4. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

External links[edit]

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