2-Bromomescaline
Clinical data
ATC code
  • none
Identifiers
  • 2-(2-Bromo-3,4,5-trimethoxyphenyl)ethanamine
CAS Number
  • 37015-19-3 ☒N
PubChem CID
ChemSpider
Chemical and physical data
FormulaC11H16BrNO3
Molar mass290.157 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C(C(=C1)CCN)Br)OC)OC
  • InChI=1S/C11H16BrNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3
  • Key:UXQBKANLBLUVMK-UHFFFAOYSA-N

2-Bromomescaline (2-Br-M) is a derivative of the phenethylamine hallucinogen mescaline which has an unusual 2-bromo substitution.[1][2] It is an agonist for serotonin receptors, with a binding affinity of 215 nM at 5-HT1A, 513 nM at 5-HT2A and 379 nM at 5-HT2C, so while it is around ten times more tightly binding than mescaline at 5-HT1A and 5-HT2A receptors, it is over twenty times more potent at 5-HT2C.[3]

See also

References

  1. ^ Shulgin A, Manning T, Daley PF (2011). The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press. p. 280–281, 355. ISBN 978-0-9630096-3-0.
  2. ^ Pecherer B, Sunbury RC, Brossi A (June 1972). "A novel synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5-tetrahydro-1H3-benzazepines". Journal of Heterocyclic Chemistry. 9 (3): 609–616. doi:10.1002/jhet.5570090322.
  3. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 908–910. ISBN 978-3-03788-700-4.