2,5-Dimethoxy-4-chloroamphetamine

DOC
Clinical data
Other names	DOC; 2,5-Dimethoxy-4-chloroamphetamine; 4-Chloro-2,5-dimethoxyamphetamine
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	AU: Unscheduled; BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Unscheduled; UN: Psychotropic Schedule I;
Pharmacokinetic data
Duration of action	12–24 hours
Identifiers
	IUPAC name 1-(4-Chloro-2,5-dimethoxyphenyl)propan-2-amine;
CAS Number	123431-31-2 ;
PubChem CID	542036;
ChemSpider	472008 ;
UNII	8Y1C6K0PCA;
KEGG	C22719 ;
ChEMBL	ChEMBL8100 ;
CompTox Dashboard (EPA)	DTXSID60894189 ;
ECHA InfoCard	100.215.939
Chemical and physical data
Formula	C11H16ClNO2
Molar mass	229.70 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=C(OC)C=C(CC(C)N)C(OC)=C1;
	InChI InChI=1S/C11H16ClNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 ; Key:ACRITBNCBMTINK-UHFFFAOYSA-N ;
	(verify)

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is taken orally.

The drug acts as a serotonin 5-HT₂ receptor agonist, including of the serotonin 5-HT_2A receptor. Analogues of DOC include 2C-C, DOB, DOI, DOM, among others.

DOC was first described in the scientific literature by Ronald Coutts and Jerry Malicky in 1973. Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Recreational availability and use of DOC are rare. The drug is expected to become a controlled substance in the United States in the near future as of 2025.