2C-B-OH

2C-B-OH
Clinical data
Other names	4-Bromo-2,5-dimethoxy-N-hydroxyphenethylamine; 2,5-Dimethoxy-4-bromo-N-hydroxyphenethylamine; N-Hydroxy-4-bromo-2,5-dimethoxyphenethylamine; N-Hydroxy-2C-B
ATC code	None;
Identifiers
	IUPAC name N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]hydroxylamine;
PubChem CID	129849638;
Chemical and physical data
Formula	C10H14BrNO3
Molar mass	276.130 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C=C1CCNO)OC)Br;
	InChI InChI=1S/C10H14BrNO3/c1-14-9-6-8(11)10(15-2)5-7(9)3-4-12-13/h5-6,12-13H,3-4H2,1-2H3; Key:BXSZGYIMATXPNW-UHFFFAOYSA-N;

2C-B-OH, also known as 4-bromo-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-B, is a chemical compound of the phenethylamine and 2C families related to the psychedelic drug 2C-B.^[1] It is the N-hydroxy derivative of 2C-B and is structurally related to the HOT-x psychedelics like HOT-2 (N-hydroxy-2C-T-2), HOT-7 (N-hydroxy-2C-T-7), and HOT-17 (N-hydroxy-2C-T-17).^[2] Unlike the HOT-x drugs however, 2C-B-OH was not included nor mentioned by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[2] The HOT-x psychedelics, as well as the MDxx entactogens MDOH (N-hydroxy-MDA) and FLEA (MDMOH; N-hydroxy-MDMA), may act as prodrugs of their N-unsubstituted analogues, for instance HOT-2 into 2C-T-2.^[2] The chemical synthesis of 2C-B-OH has been described.^[1] The drug was first described in the scientific literature by Leth-Petersen and colleagues in 2016.^[1]

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See also