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para-Bromoamphetamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
para-Bromoamphetamine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(4-bromophenyl)propan-2-amine
CAS Number
PubChemCID
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 as4-bromoamphetamine (4-BA), is anamphetamine derivative which acts as aserotonin-norepinephrine-dopaminereleasing agent (SNDRA) and producesstimulant effects.

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

Pharmacology

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PBA has been found to be amonoamine oxidase A (MAO-A)inhibitor, with anIC50Tooltip half-maximal inhibitory concentration of 1,500 nM.[2]

Neurotoxicity

[edit]

Like most otherpara-substitutedamphetamines, PBA can beneurotoxic and may deplete the brain of 5-hydroxyindoles for at least a week.[3]

6-BAT

[edit]

Given that6-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

[edit]
  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).
Dopaminergic
Noradrenergic
Serotonergic
Unsorted
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=Para-Bromoamphetamine&oldid=1306806115"
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