2,5-Dimethoxy-3-bromoamphetamine

3-DOB
Clinical data
Other names3-Br-2,5-DMA; 3-DOB; iso-DOB; SL-7161; 2,5-Dimethoxy-3-bromoamphetamine; 3-Bromo-2,5-dimethoxyamphetamine
Drug classPsychoactive drug; Serotonin receptor modulator
ATC code
  • None
Legal status
Legal status
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC11H16BrNO2
Molar mass274.158 g·mol−1
3D model (JSmol)
  • COc1cc(CC(N)C)c(c(c1)Br)OC
  • InChI=InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(14-2)6-10(12)11(8)15-3/h5-7H,4,13H2,1-3H3
  • Key:HCZXNFSMGJKVHO-UHFFFAOYSA-N

2,5-Dimethoxy-3-bromoamphetamine, also known as 3-Br-2,5-DMA, 3-DOB, or iso-DOB, is a psychoactive compound belonging to the family of substituted phenеthylamines and amphetamine derivatives. It is a positional isomer of 4-bromo-2,5-dimethoxyamphetamine (DOB; 4-Br-2,5-DMA) and a derivative of 2,5-dimethoxyamphetamine (2,5-DMA; DOH) where the hydrogen atom in the 3 position of the benzene ring is replaced by bromine. 3-Br-2,5-DMA exhibits agonistic activity against serotonin 5-HT2 and 5-HT3 receptors.[1][2] In The Shulgin Index, 3-Br-2,5-DMA was referred to as "3-DOB"[3]

Pharmacology

Pharmacodynamics

3-Br-2,5-DMA demonstrated weak or even low psychoactivity, unlike its isomers, and did not have a significant effect on the activity of neurons in the locus coeruleus. Despite the structural difference, it is precisely because of the positional difference from other isomers that this substance exhibits a low psychoactive effect, 3-Br-2,5-DMA It did not cause any behavioral changes or hallucinogenic effects, it is noted that this substance is of "inactive".[4] 3-Br-2,5-DMA binds to serotonin receptors approximately 50 to 60 times weaker than DOB.[5]

Chemistry

Synthesis

3-Br-2,5-DMA can be successfully obtained from nitropropene. Synthesis of the 3-Br-2,5-DMA requires the use of aluminum hydride (AlH3) instead of the standard lithium aluminum hydride, since the latter causes a dehalogenation side reaction leading to the elimination of a bromine atom.[5]

History

3-DOB was first described in the scientific literature by Richard Glennon and colleagues by 1980.[5]

See also

References

  1. ^ Merahi N, Laguzzi R (January 1995). "Cardiovascular effects of 5HT2 and 5HT3 receptor stimulation in the nucleus tractus solitarius of spontaneously hypertensive rats". Brain Research. 669 (1): 130–134. doi:10.1016/0006-8993(94)01202-s. PMID 7712156.
  2. ^ Merahi N, Orer HS, Laguzzi R (March 1992). "5-HT2 receptors in the nucleus tractus solitarius: characterisation and role in cardiovascular regulation in the rat". Brain Research. 575 (1): 74–78. doi:10.1016/0006-8993(92)90425-9. PMID 1504784.
  3. ^ "3-DOB | explore | PiHKAL·info". isomerdesign.com. Retrieved 2026-02-22.
  4. ^ Rasmussen K, Glennon RA, Aghajanian GK (December 1986). "Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity". European Journal of Pharmacology. 132 (1): 79–82. doi:10.1016/0014-2999(86)90014-2. PMID 3816969.
  5. ^ a b c Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
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