64638-07-9

Basic information

• Product Name: Brolamfetamine
• Synonyms: Brolamfetamine;4-bromo-2,5-dimethoxyamphetamine;dl-2,5-Dimethoxy-4-bromoamphetamine;(+-)-1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane;4-Bromo-2,5-dimethoxyphenylisopropylamine;4-Bromo-dma;Benzeneethanamine, 4-bromo-2,5-dimethoxy-alpha-methyl-;Benzeneethanamine, 4-bromo-2,5-dimethoxy-alpha-methyl-, (+-)-
• CAS NO: 64638-07-9
• Molecular Formula: C₁₁H₁₆BrNO₂
• Molecular Weight: 274.15754
• Product Categories: Amines;Aromatics
• Mol File: 64638-07-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 67-70°C
• Boiling Point: 340.8 °C at 760 mmHg
• Flash Point: 159.9 °C
• Appearance: /
• Density: 1.324 g/cm³
• Vapor Pressure: 8.37E-05mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Store at RT
• PKA: 9.41±0.10(Predicted)
• CAS DataBase Reference: Brolamfetamine(CAS DataBase Reference)
• NIST Chemistry Reference: Brolamfetamine(64638-07-9)
• EPA Substance Registry System: Brolamfetamine(64638-07-9)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 64638-07-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

2,5-Dimethoxy-4-bromoamphetamine (DOB) is one of the potent hallucinogenic phenylalkylamines with neurotoxic properties.

Biological Activity

Selective 5-HT 2 receptor agonist (K i values are 0.44, 59, 69, 831 and 3700 nM for 5-HT 2H , 5-HT 2L , 5-HT 2C , 5-HT 1B and 5-HT 1A receptors respectively). Hallucinogenic.

InChI:InChI=1/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3

Upstream product

• 2801-68-5 2,5-dimethoxyphenylisopropylamine 
• 42311-16-0 (+/-)-N-acetyl-1-(2,5-dimethoxyphenyl)-2-aminopropane 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 
• 42203-75-8 N-acetyl-2,5-dimethoxy-4-bromo-amphetamine 
• 82040-77-5 1-(2,5-dimethoxy-4-bromophenyl)-2-nitropropene 

Downstream Products

• 952016-31-8 1-[2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethyl]-2,2,5,5-tetramethyl-[1,2,5]azadisilolidine 
• 125903-52-8 4-(2-Amino-propyl)-2,5-dimethoxy-benzoic acid butyl ester 
• 125903-50-6 4-(2-Amino-propyl)-2,5-dimethoxy-benzoic acid propyl ester 
• 125903-55-1 N-n-propyl-2,5-dimethoxy-4-(2-aminopropyl)benzamide 
• 121649-10-3 (+/-)-1-<2,5-Dimethoxy-4-(2-tosyloxyethyl)phenyl>-2-trifluoroacetamidopropane 
• 121649-07-8 (+/-)-1-<2,5-Dimethoxy-4-(2-fluoroethyl)phenyl>-2-trifluoroacetamidopropane 
• 121649-06-7 (+/-)-1-<2,5-Dimethoxy-4-(2-hydroxyethyl)phenyl>-2-trifluoroacetamidopropane 
• 121649-08-9 (+/-)-1-<2,5-Dimethoxy-4-(ethen)phenyl>-2-trifluoroacetamidopropane 
• 121649-04-5 2-[4-(2-Amino-propyl)-2,5-dimethoxy-phenyl]-ethanol 
• 121649-01-2 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine 
• 155639-42-2 N-[2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethyl]-4-phenyl-butyramide 
• 29907-75-3 1-(4-carboxy-2,5-dimethoxyphenyl)-2-aminopropane 
• 107271-31-8 N,N-dimethyl-1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane 

Relevant articles and documents

Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists

The 2,5-dimethoxyphenethylamine (2,5-PEA) scaffold is recognized as a motif conferring potent agonist activity at the serotonin 2A receptor (5-HT2AR). The 2,5-dimethoxy motif is present in several classical phenethylamine psychedelics such as 2

5-HT1 and 5-HT2 Binding Characteristics of 1-(2,5-Dimethoxy-4-bromophenyl)-2-aminopropane Analogues

1-(2,5-Dimethoxy-4-bromophenyl)-2-aminopropane (DOB; 1a) is a purported serotonin (5-HT) agonist that binds selectively to central 5-HT2 binding sites.Systematic removal of any or all of the aromatic substituents had relatively little effect on 5-HT1 binding but reduced 5-HT2 binding by approximately 2 or more orders of magnitude.Demethylation of the 2-methoxy group of 1a, or introduction of N-n-propyl group, doubled 5-HT1-site affinity but decreased 5-HT2-site affinity by 3- and 30-fold, respectively.In tests of stimulus generalization, using rats trained to discriminate DOM from saline, the 2-demethyl and N-propyl derivatives were found to produce stimulus effects similar to those of DOB.In addition, the S-(+) isomer of the iodo analogue of 1a was found to possess one-third the affinity of its R-(-) enantiomer at 5-HT2 sites and also resulted in DOM-stimulus generalization.Of the DOB analogues examined, DOB (1a) possesses optimal selectivity for 5-HT2 binding.

Potential psychotomimetics. Bromomethoxyamphetamines.

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