Article · Wikipedia archive · Last revised Jun 18, 2026

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. It is the DOx derivative with a benzyl ring at the 4 position.

Last revised
Jun 18, 2026
Read time
≈ 3 min
Length
640 w
Citations
14
Source
Wikipedia ↗
DOBz
Clinical data
Other namesDOBz; DOBZ; DOBN; DOBn; 4-Benzyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-benzylamphetamine
Drug classSerotonin 5-HT2 receptor modulator
ATC code
  • None
Identifiers
  • 1-(4-benzyl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC18H23NO2
Molar mass285.387 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=C(C(=C1)OC)CC2=CC=CC=C2)OC)N
  • 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

2,5-Dimethoxy-4-benzylamphetamine (DOBz or DOBN) is a serotonin 5-HT2 receptor modulator of the amphetamine and DOx families.123 It is the DOx derivative with a benzyl ring at the 4 position.1

The drug's affinities (Ki) for the human serotonin 5-HT2 receptors have been found to be 0.40 nM for the serotonin 5-HT2A receptor, 24.5 to 35.0 nM for the serotonin 5-HT2B receptor, and 1.0 nM for the serotonin 5-HT2C receptor.14 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-HT2B receptor (EmaxTooltip maximal efficacy = 0%).4 In rodent drug discrimination tests, DOBz neither antagonized nor generalized to the stimulus of DOM.56 Higher doses produced behavioral disruption however.5

DOBz was first described in the scientific literature by Richard Glennon and colleagues in 1989.57 It is a controlled substance in Canada under phenethylamine blanket-ban language.8

See also

See also

References

References

  1. Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (January 1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch Pharmacol. 359 (1): 1–6. doi:10.1007/pl00005315. PMID 9933142.
  2. Blaazer AR, Smid P, Kruse CG (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors". ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. PMID 18666267. Studies on the homologation of phenylisopropylamines at the 4-position found a decrease of in vivo hallucinogenic potency beyond n-propyl.[163] Yet later work using [3 H]ketanserin as a radioligand for 5-HT2 receptors in rat brain homogenate revealed significantly increased binding affinities with the more lipophilic derivatives; n-hexyl and n-octyl derivatives showed the highest binding affinity. After in vitro testing, these derivatives were found to act as 5-HT2 receptor antagonists.[67] Using [125I]DOI labeled human receptor data, the highest binding affinity at 5-HT2A receptors was found for the 4-nhexyl analogue DOHx (21, Ki=0.1 nm), followed by the 4- benzyl analogue DOBz (22, Ki=0.4 nm), DOB (16, Ki=0.6 nm), DOI (17, Ki=0.7 nm), and the 4-n-propyl analogue DOPR (23, Ki=0.9 nm).[63]
  3. Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. Replacing the halogen on the 4-position with a methyl group led to significantly reduced activity (91, DOM, Ki = 100 nM), but the activity could be restored with longer linear alkyl chains and the benzyl group, such as compounds DOPR (92, Ki = 0.9 nM), DOHx (93, Ki = 0.1 nM), and DOBz (94, Ki = 0.4 nM).172 Interestingly, these DOXs compounds also exhibited some selectivity against the 5- HT2BR and 5-HT2CR.172
  4. Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M (2023). "Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors". Front Pharmacol. 14 1101290. doi:10.3389/fphar.2023.1101290. PMC 9902381. PMID 36762110.
  5. Glennon RA, Seggel MR (14 November 1989). "Interaction of Phenylisopropylamines with Central 5-HT2 Receptors: Analysis by Quantitative Structure—Activity Relationships". Probing Bioactive Mechanisms. Vol. 413. Washington, DC: American Chemical Society. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7.
  6. Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Res Monogr. 94: 43–67. PMID 2575229. Archived from the original (PDF) on May 11, 2023.
  7. Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors" (PDF). J Med Chem. 33 (3): 1032–1036. doi:10.1021/jm00165a023. PMID 2308135.
  8. "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
External links