Chemistry:Para-Bromoamphetamine

*para*-Bromoamphetamine
Clinical data
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 ;
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 ;
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Short description: Chemical 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 known by the codename V-111.^[1]

Neurotoxicity

Like most other para-substituted amphetamines, PBA can be neurotoxic and may deplete the brain of 5-hydroxyindoles for at least a week.^[2]

References

↑ "The fate of p-bromo-methylamphetamine (V-111) in the body". Acta Physiologica Academiae Scientiarum Hungaricae 57 (3): 285–307. 1981. PMID 7304194.
↑ "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. October 1975. doi:10.1016/0028-3908(75)90099-4. PMID 1196472.

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[pmid7304194-1] "The fate of p-bromo-methylamphetamine (V-111) in the body". Acta Physiologica Academiae Scientiarum Hungaricae 57 (3): 285–307. 1981. PMID 7304194.

[haloampcomparison-2] "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. October 1975. doi:10.1016/0028-3908(75)90099-4. PMID 1196472.

[1]

[2]

v t e Monoamine neurotoxins
Adrenergic	DSP-4 Oxidopamine (6-OHDA)
Dopaminergic	Fenpropathrin Methamphetamine MPP⁺ MPTP Norsalsolinol Oxidopamine (6-OHDA) Rotenone
Serotonergic	3-CA 4-CAB 5,7-DHT α-Me-DA (3,4-DHA) αET αMT DCA MDA (tenamfetamine) MDMA (midomafetamine) PBA PCA PIA
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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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
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)

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