Para-Bromoamphetamine

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para-Bromoamphetamine
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • 1-(4-bromophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H12BrN
Molar mass214.106 g·mol−1
3D model (JSmol)
  • Brc1ccc(cc1)CC(N)C
  • InChI=1S/C9H12BrN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 checkY
  • Key:SMNXUMMCCOZPPN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

para-Bromoamphetamine (PBA), also known as 4-bromoamphetamine (4-BA), is an amphetamine derivative which acts as a serotonin-norepinephrine-dopamine releasing agent (SNDRA) and produces stimulant effects.

Another related compound is para-bromomethamphetamine (PBMA) known by the codename V-111.[1]

Pharmacology

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PBA has been found to be a monoamine oxidase A (MAO-A) inhibitor, with an IC50Tooltip half-maximal inhibitory concentration of 1,500 nM.[2]

Neurotoxicity

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Like most other para-substituted amphetamines, PBA can be neurotoxic and may deplete the brain of 5-hydroxyindoles for at least a week.[3]

6-BAT

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Given that 6-CAT is a non-neurotoxic version of para-chloroamphetamine, it is worth considering 6-BAT as well.

6-BAT
6-BAT

The chemical name for this is 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine or 6-bromo-2-aminotetralin [167355-41-1] [867-970-2]. The synthesis method is disclosed (Ex 32).[4][5] The precursor is called 6-Bromo-2-tetralone [4133-35-1] [640-168-8] (Ex 16).[6]

See also

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References

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  1. ^ Magyar K, Tekes K, Zólyomi G, Szüts T, Knoll J (1981). "The fate of p-bromo-methylamphetamine (V-111) in the body". Acta Physiologica Academiae Scientiarum Hungaricae. 57 (3): 285–307. PMID 7304194.
  2. ^ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
  3. ^ Fuller RW, Baker JC, Perry KW, Molloy BB (October 1975). "Comparison of 4-chloro-, 4-bromo- and 4-fluoroamphetamine in rats: drug levels in brain and effects on brain serotonin metabolism". Neuropharmacology. 14 (10): 739–46. doi:10.1016/0028-3908(75)90099-4. PMID 1196472. S2CID 9620299.
  4. ^ Armin Heckel, et al. U.S. patent 5,681,961 (1997 to Boehringer Ingelheim Pharma GmbH and Co KG).
  5. ^ Margaretha, P., Science of Synthesis, (2009) 40, 137. DOI: 10.1055/sos-SD-040-00073.
  6. ^ Werner Aschwanden,et al. U.S. patent 4,957,911 (1990 to Hoffmann La Roche Inc).