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).^[2]

^ 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.
^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. United States: Transform Press. p. 978. ISBN 0-9630096-0-5. Archived from the original on 3 January 2010. Retrieved 30 November 2009.

[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. Archived from the original on 3 January 2010. Retrieved 30 November 2009.

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