XOB

XOB, also known as ASR-6001 or as N-[(4-phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine, is a serotonin 5-HT_2A 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]

Other namesASR-6001; ASR6001; N-[(4-Phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine

Drug classSerotonin 5-HT_2A receptor antagonist; Voltage-gated sodium channel blocker

ATC code

• None

PubChem CID

• 170703346

Quick facts Clinical data, Other names ...

XOB

Clinical data
Other names	ASR-6001; ASR6001; N-[(4-Phenylbutoxy)hexyl]-4-bromo-2,5-dimethoxyphenethylamine
Drug class	Serotonin 5-HT2A receptor antagonist; Voltage-gated sodium channel blocker
ATC code	None
Identifiers
IUPAC name N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-6-(4-phenylbutoxy)hexan-1-amine
PubChem CID	170703346
Chemical and physical data
Formula	C26H38BrNO3
Molar mass	492.498 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1CCNCCCCCCOCCCCC2=CC=CC=C2)OC)Br
InChI 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

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The drug is of relatively low potency as a serotonin 5-HT_2A receptor antagonist.^[1] It shows modest selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2B and 5-HT_2C 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]