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

References

{{Reflist}}

{{Monoamine neurotoxins}}

{{Monoamine releasing agents}}

{{Phenethylamines}}

{{DEFAULTSORT:Bromoamphetamine, para-}}

Category:4-Bromophenyl compounds

Category:Monoaminergic neurotoxins

Category:Serotonin-norepinephrine-dopamine releasing agents

Category:Substituted amphetamines