2C-B-OH

Last updated

2C-B-OH
2C-B-OH.svg
Clinical data
Other names4-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
  • N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]hydroxylamine
PubChem CID
Chemical and physical data
Formula C10H14BrNO3
Molar mass 276.130 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1CCNO)OC)Br
  • 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 or 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]

Contents

See also

References

  1. 1 2 3 Leth-Petersen S, Gabel-Jensen C, Gillings N, Lehel S, Hansen HD, Knudsen GM, et al. (January 2016). "Metabolic Fate of Hallucinogenic NBOMes". Chemical Research in Toxicology. 29 (1): 96–100. doi:10.1021/acs.chemrestox.5b00450. PMID   26669514. [Supporting Information] [...] Entry 35: N-(4-bromo-2,5-dimethoxyphenethyl)hydroxylamine [...]
  2. 1 2 3 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.