2,5-Dimethoxy-4-benzylamphetamine

2,5-Dimethoxy-4-benzylamphetamine (DOBz or DOBN) is a serotonin 5-HT₂ receptor modulator of the amphetamine and DOx families.^[1][2][3] It is the DOx derivative with a benzyl ring at the 4 position.^[1]

2,5-Dimethoxy-4-benzylamphetamine

Clinical data
Other names	DOBz; DOBZ; DOBN; DOBn; 4-Benzyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-benzylamphetamine
Drug class	Serotonin 5-HT2 receptor modulator
Identifiers
IUPAC name 1-(4-benzyl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number	125903-73-3
PubChem CID	24039384
ChemSpider	23108642
ChEMBL	ChEMBL274589
Chemical and physical data
Formula	C18H23NO2
Molar mass	285.387 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=C(C=C(C(=C1)OC)CC2=CC=CC=C2)OC)N
InChI InChI=1S/C18H23NO2/c1-13(19)9-15-11-18(21-3)16(12-17(15)20-2)10-14-7-5-4-6-8-14/h4-8,11-13H,9-10,19H2,1-3H3 Key:FQARCNZVKSYIGI-UHFFFAOYSA-N

The drug's affinities (K_i) for the human serotonin 5-HT₂ receptors have been found to be 0.40 nM for the serotonin 5-HT_2A receptor, 24.5 to 35.0 nM for the serotonin 5-HT_2B receptor, and 1.0 nM for the serotonin 5-HT_2C receptor.^[1][4] Its affinities for the serotonin 5-HT₂ receptors are very similar to those of DOB.^[1] The drug has been assessed and found to act as a silent antagonist of the serotonin 5-HT_2B receptor (E_maxTooltip maximal efficacy = 0%).^[4] In rodent drug discrimination tests, DOBz neither antagonized nor generalized to the stimulus of DOM.^[5][6] Higher doses produced behavioral disruption however.^[5]

DOBz was first described in the scientific literature by Richard Glennon and colleagues in 1989.^[5][7]

See also

• 2C-Ph
• 4-PhPr-2,5-DMA
• 2C-T-27
• Benzscaline (BZ)
• 3C-BZ