2,5-Dimethoxy-4-ethylamphetamine

2,5-Dimethoxy-4-ethylamphetamine
Clinical data
Other names	2,5-dimethoxy-4-ethylamphetamine
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine;
CAS Number	22004-32-6 ;
PubChem CID	27402;
DrugBank	DB01467 ;
ChemSpider	25499 ;
UNII	9SK6K682UL;
KEGG	C22714 ;
ChEMBL	ChEMBL8224 ;
CompTox Dashboard (EPA)	DTXSID00860585 ;
Chemical and physical data
Formula	C13H21NO2
Molar mass	223.316 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:HXJKWPGVENNMCC-UHFFFAOYSA-N ;
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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).^[2]

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-HT_2A, 5-HT_2B, and 5-HT_2C receptor partial agonist.^{[citation needed]} It is an agonist of human TAAR1.^[3]^[4]

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.^[2]

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).^[5] 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.^[5]

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.
^ ^a ^b Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5.
^ Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorganic & Medicinal Chemistry. 19 (23): 7044–7048. doi:10.1016/j.bmc.2011.10.007. PMC 3236098. PMID 22037049.
^ "Compound ID: CHEMBL2360469". ChEMBL. Retrieved 29 April 2014.
^ ^a ^b "Poisons Standard". Therapeutics Goods Administration. Australian Government. October 2015.

External links

[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.

[PiHKAL-2] Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5.

[3] Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorganic & Medicinal Chemistry. 19 (23): 7044–7048. doi:10.1016/j.bmc.2011.10.007. PMC 3236098. PMID 22037049.

[4] "Compound ID: CHEMBL2360469". ChEMBL. Retrieved 29 April 2014.

[Poisons_Standard-5] "Poisons Standard". Therapeutics Goods Administration. Australian Government. October 2015.

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