Brolamfetamine

Base Information

• Chemical Name: Brolamfetamine
• CAS No.: 64638-07-9
• Deprecated CAS: 32156-26-6
• Molecular Formula: C11H16BrNO2
• Molecular Weight: 274.158
• UNII: 67WJC4Y2QY
• DSSTox Substance ID: DTXSID5050428
• Nikkaji Number: J275.083J
• Wikipedia: 2,5-Dimethoxy-4-bromoamphetamine
• Wikidata: Q209241
• NCI Thesaurus Code: C80757
• Pharos Ligand ID: C9GATFCCWGPA
• Metabolomics Workbench ID: 146139
• ChEMBL ID: CHEMBL6607
• Mol file: 64638-07-9.mol

Synonyms:1-(2,5-dimethoxyphenyl-4-bromo)-2-aminopropane;1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane;2,5-dimethoxy-(4-bromo)phenylisopropylamine;2,5-dimethoxy-4-bromoamphetamine;2,5-dimethoxy-4-bromoamphetamine monohydrochloride;2,5-dimethoxy-4-bromoamphetamine, (+-)-isomer;2,5-dimethoxy-4-bromoamphetamine, (beta)-(+-)-isomer;2,5-dimethoxy-4-bromoamphetamine, (beta)-isomer;2,5-dimethoxy-4-bromoamphetamine, (R)-isomer;2,5-dimethoxy-4-bromoamphetamine, (S)-isomer;2,5-dimethoxy-4-bromoamphetamine, 77Br-labeled;2,5-dimethoxy-4-bromoamphetamine, 82Br-labeled;2,5-dimethoxy-4-bromoamphetamine, monohydrobromide, (+-)-isomer;2,5-dimethoxy-4-bromoamphetamine, monohydrobromide, (R)-isomer;2,5-dimethoxy-4-bromoamphetamine, monohydrobromide, (S)-isomer;2,5-dimethoxy-4-bromoamphetamine, monohydrochloride, (+-)-isomer;2,5-dimethoxy-4-bromoamphetamine, monohydrochloride, (R)-isomer;2,5-dimethoxy-4-bromoamphetamine, monohydrochloride, (S)-isomer;4-bromo-2,5-dimethoxyamphetamine;4-bromo-2,5-dimethoxyphenylisopropylamine;4-DOB;DOB-4

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Chemical Property of Brolamfetamine

Chemical Property:

• Vapor Pressure: 8.37E-05mmHg at 25°C
• Melting Point: 67-70°C
• Refractive Index: 1.54
• Boiling Point: 340.8 °C at 760 mmHg
• PKA: 9.41±0.10(Predicted)
• Flash Point: 159.9 °C
• PSA: 44.48000
• Density: 1.324 g/cm³
• LogP: 3.05630
• Storage Temp.: Store at RT
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 273.03644
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C=C1OC)Br)OC)N
• Uses: 2,5-Dimethoxy-4-bromoamphetamine (DOB) is one of the potent hallucinogenic phenylalkylamines with neurotoxic properties.

Technology Process of Brolamfetamine

There total 6 articles about Brolamfetamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

1-(2,5-dimethoxy-4-bromophenyl)-2-nitropropene (82040-77-5) → 4-bromo-2,5-dimethoxyphenylisopropylamine (64638-07-9)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1021/jm00152a005

Reference yield:

4-bromo-2,5-dimethoxybenzaldehyde (31558-41-5) → 4-bromo-2,5-dimethoxyphenylisopropylamine (64638-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium acetate / 1.) reflux, 8 h, 2.) RT, 60 h

2: LiAlH₄, H₂SO₄ / tetrahydrofuran / Ambient temperature

With ammonium acetate; lithium aluminium tetrahydride; sulfuric acid; In tetrahydrofuran;

DOI:10.1021/jm00082a014

Reference yield:

2,5-dimethoxyphenylisopropylamine (2801-68-5) → 4-bromo-2,5-dimethoxyphenylisopropylamine (64638-07-9)

Guidance literature:

With hydrogen bromide; bromine; In acetic acid;

DOI:10.1021/jm00256a016

upstream raw materials:

2,5-dimethoxyphenylisopropylamine

1-(2,5-dimethoxy-4-bromophenyl)-2-nitropropene

N-acetyl-2,5-dimethoxy-4-bromo-amphetamine

4-bromo-2,5-dimethoxybenzaldehyde

Downstream raw materials:

1-(4-carboxy-2,5-dimethoxyphenyl)-2-aminopropane

N,N-dimethyl-1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane

4-(2-Amino-propyl)-2,5-dimethoxy-benzoic acid butyl ester

4-(2-Amino-propyl)-2,5-dimethoxy-benzoic acid propyl ester

Refernces

• 1、 Glennon, Richard A.,Raghupathi, Reva,Bartyzel, Piotr,Teitler, Milt,Leonhardt, Sigrun. "Binding of Phenylalkylamine Derivatives at 5-HT1C and 5-HT2 Serotonin Receptors: Evidence for a Lack of Selectivity". . p. 734 - 740. Retrieved 2007/10/02.
• 2、 Coutts,Malicky. "The synthesis of some analogs of the hallucinogen 1 (2,5 dimethoxy 4 methylphenyl) 2 aminopropane (DOM)". . p. 1402 - 1409. Retrieved 2007/10/05.