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 N;
PubChem CID	205668;
ChemSpider	178189 Y;
UNII	6IBU62D1N2;
ChEMBL	ChEMBL61355 Y;
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 Y; Key:SMNXUMMCCOZPPN-UHFFFAOYSA-N Y;
	NY (what is this?) (verify)

Chemical compound

Pharmaceutical compound

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.

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.
↑ 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.

[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).

[1]

[3]

[4]

[5]

[6]

v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine V-61 Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP⁺ HPTP Imidazole propionate (ImP) Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP⁺ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol TaClo (1-TCMTC) Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine V-61
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA pCPE 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP⁺ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI
Unsorted	2,5-DDM-DOM 5-HIAL RHPP⁺ RHPTP
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

Pharmacology

Neurotoxicity

6-BAT

See also

References