2,5-Dimethoxy-4-acetylamphetamine

DOAc
Clinical data
Other names	2,5-Dimethoxy-4-acetylamphetamine; 4-Acetyl-2,5-dimethoxyamphetamine; DOAc; DOAC
Drug class	Serotonin 5-HT2 receptor modulator
ATC code	None;
Identifiers
	IUPAC name 1-[4-(2-aminopropyl)-2,5-dimethoxyphenyl]ethanone;
PubChem CID	23983771;
ChemSpider	34948069;
Chemical and physical data
Formula	C13H19NO3
Molar mass	237.299 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1OC)C(=O)C)OC)N;
	InChI InChI=1S/C13H19NO3/c1-8(14)5-10-6-13(17-4)11(9(2)15)7-12(10)16-3/h6-8H,5,14H2,1-4H3; Key:NWWLLPGDGZOZAT-UHFFFAOYSA-N;

2,5-Dimethoxy-4-acetylamphetamine (DOAc) is a serotonin 5-HT₂ receptor modulator of the amphetamine and DOx families.^[1] Its affinities (K_i) for the human serotonin 5-HT₂ receptors are 80.5 nM for the serotonin 5-HT_2A receptor, 313 nM for the serotonin 5-HT_2B receptor, and 91.3 nM for the serotonin 5-HT_2C receptor.^[1] These affinities are much lower than those of many other DOx derivatives, such as DOB, but are very similar to those of 3,4,5-trimethoxyamphetamine (TMA).^[1] DOAc is a controlled substance in Canada under phenethylamine blanket-ban language.^[2]

References

1 2 3 Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch Pharmacol. 359 (1): 1–6. doi:10.1007/pl00005315. PMID 9933142.
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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