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; 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;
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 was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved).

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; 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
Identifiers
IUPAC name 1-(4-Chloro-2,5-dimethoxyphenyl)propan-2-amine
CAS Number	123431-31-2^Y
PubChem CID	542036
ChemSpider	472008^Y
UNII	8Y1C6K0PCA
KEGG	C22719^Y
ChEMBL	ChEMBL8100^Y
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^Y Key:ACRITBNCBMTINK-UHFFFAOYSA-N^Y
(verify)