para-Bromoamphetamine
{{Short description|Chemical compound}}
{{DISPLAYTITLE:para-Bromoamphetamine}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462272913
| IUPAC_name = 1-(4-bromophenyl)propan-2-amine
| image = 4-bromoamphetamine.svg
| image_class = skin-invert-image
| image2 = 4-BA44.jpg
| width = 200px
| drug_name = para-Bromoamphetamine
| tradename =
| legal_DE = NpSG
| legal_UK = Class A
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 18455-37-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6IBU62D1N2
| ATC_prefix = none
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 61355
| PubChem = 205668
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 178189
| C=9 | H=12 | Br=1 | N=1
| smiles = Brc1ccc(cc1)CC(N)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H12BrN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SMNXUMMCCOZPPN-UHFFFAOYSA-N
}}
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.{{cite journal | vauthors = Magyar K, Tekes K, Zólyomi G, Szüts T, Knoll J | title = The fate of p-bromo-methylamphetamine (V-111) in the body | journal = Acta Physiologica Academiae Scientiarum Hungaricae | volume = 57 | issue = 3 | pages = 285–307 | date = 1981 | pmid = 7304194 | doi = | url = }}
Pharmacology
PBA has been found to be a monoamine oxidase A (MAO-A) inhibitor, with an {{Abbrlink|IC50|half-maximal inhibitory concentration}} of 1,500{{nbsp}}nM.{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | pages = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}
Neurotoxicity
Like most other para-substituted amphetamines, PBA can be neurotoxic and may deplete the brain of 5-hydroxyindoles for at least a week.{{cite journal | vauthors = Fuller RW, Baker JC, Perry KW, Molloy BB | title = Comparison of 4-chloro-, 4-bromo- and 4-fluoroamphetamine in rats: drug levels in brain and effects on brain serotonin metabolism | journal = Neuropharmacology | volume = 14 | issue = 10 | pages = 739–46 | date = October 1975 | pmid = 1196472 | doi = 10.1016/0028-3908(75)90099-4 | s2cid = 9620299 }}
See also
- Substituted amphetamines
- 4-Bromomethcathinone (4-BMC)
- 4-Fluoroamphetamine (4-FA)
- para-Chloroamphetamine (PCA)
- para-Iodoamphetamine (PIA)
- para-Bromomethamphetamine (PBMA)
References
{{Reflist}}
{{Monoamine neurotoxins}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
{{DEFAULTSORT:Bromoamphetamine, para-}}
Category:4-Bromophenyl compounds
Category:Monoaminergic neurotoxins