XOB

XOB
Clinical data
Other namesASR-6001; ASR6001; N-[(4-Phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine
Drug classSerotonin 5-HT2A receptor antagonist; Voltage-gated sodium channel blocker
ATC code
  • None
Identifiers
  • N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-6-(4-phenylbutoxy)hexan-1-amine
PubChem CID
Chemical and physical data
FormulaC26H38BrNO3
Molar mass492.498 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1CCNCCCCCCOCCCCC2=CC=CC=C2)OC)Br
  • InChI=1S/C26H38BrNO3/c1-29-25-21-24(27)26(30-2)20-23(25)15-17-28-16-9-3-4-10-18-31-19-11-8-14-22-12-6-5-7-13-22/h5-7,12-13,20-21,28H,3-4,8-11,14-19H2,1-2H3
  • Key:GOUKDEUQBCARRO-UHFFFAOYSA-N

XOB, also known as ASR-6001 or as N-[(4-phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine, is a serotonin 5-HT2A receptor antagonist and voltage-gated sodium channel (VGSC) blocker of the phenethylamine and 2C families.[1] It is a derivative of 2C-B in which the amine-containing side chain has been extended with the same long group found in salmeterol.[1]

The drug is of relatively low potency as a serotonin 5-HT2A receptor antagonist.[1] It shows modest selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2B and 5-HT2C receptors.[1] XOB was accidentally found to have local anesthetic properties upon contact with human skin, which led to the elucidation of its sodium channel-blocking activity.[1]

XOB was developed in part by researchers at the Alexander Shulgin Research Institute (ASRI).[1]

See also

References

  1. ^ a b c d e f Denomme N, Hernandez CC, Bock HA, Ohana RF, Bakshi S, Sherwood AM, McCorvy JD, Daley PF, Callaway WB, Hull JM, Alt A, Isom LL, Cozzi NV (July 2024). "N-(4-Bromo-2,5-Dimethoxyphenethyl)-6-(4-Phenylbutoxy)Hexan-1-Amine (XOB): A Novel Phenylalkylamine Antagonist of Serotonin 2A Receptors and Voltage-Gated Sodium Channels" (PDF). Mol Pharmacol. 106 (2): 92–106. doi:10.1124/molpharm.123.000837. PMID 38821630.



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