para-Bromoamphetamine

*para*-Bromoamphetamine
Clinical data
Drug class	Monoamine releasing agent
ATC code	none;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name 1-(4-bromophenyl)propan-2-amine;
CAS Number	18455-37-3 ;
PubChem CID	205668;
ChemSpider	178189 ;
UNII	6IBU62D1N2;
ChEMBL	ChEMBL61355 ;
CompTox Dashboard (EPA)	DTXSID90896914 ;
Chemical and physical data
Formula	C9H12BrN
Molar mass	214.106 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Brc1ccc(cc1)CC(N)C;
	InChI InChI=1S/C9H12BrN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 ; Key:SMNXUMMCCOZPPN-UHFFFAOYSA-N ;
	(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

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

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

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

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]

References

↑ 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.
↑ 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.
↑ 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.
↑ Armin Heckel, et al. U.S. patent 5,681,961 (1997 to Boehringer Ingelheim Pharma GmbH and Co KG).
↑ Margaretha, P., Science of Synthesis, (2009) 40, 137. DOI: 10.1055/sos-SD-040-00073.
↑ Werner Aschwanden,et al. U.S. patent 4,957,911 (1990 to Hoffmann La Roche Inc).

[pmid7304194-1] 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.

[Reyes-ParadaIturriaga-VasquezCassels2019-2] 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.

[haloampcomparison-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).

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[2]

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para-Bromoamphetamine

Contents

Pharmacology

Neurotoxicity

6-BAT

See also

References