66142-81-2

Basic information

• Product Name: (+/-) 1-(4-BROMO-2 5-DIMETHOXYPHENYL)-2&
• Synonyms: (+/-) 1-(4-BROMO-2 5-DIMETHOXYPHENYL)-2&;4-Bromo-2,5-Dimethoxyphenethyl;4-BROM-2,5-DIMETHOXYPHENYLETHYLAMIN;2-(4-bromo-2,5-dimethoxyphenyl)ethylamine;4-BROM-2,5-DIMETHOXYPHENYLETHYLAMIN, >99% (HPLC);4-bromo-2,5-methoxyphenethylamine;1-(4-bromo-2,5-dimethoxyphenyl)-2-ethanamine;Nexus, (±)-4-Bromo-2,5-dimethoxybenzeneethanamine hydrochloride
• CAS NO: 66142-81-2
• Molecular Formula: C₁₀H₁₄BrNO₂
• Molecular Weight: 296.59
• Mol File: 66142-81-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 332.9 °C at 760 mmHg
• Flash Point: 155.1 °C
• Appearance: /
• Density: 1.368 g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.548
• PKA: 9.37±0.10(Predicted)
• CAS DataBase Reference: (+/-) 1-(4-BROMO-2 5-DIMETHOXYPHENYL)-2&(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-) 1-(4-BROMO-2 5-DIMETHOXYPHENYL)-2&(66142-81-2)
• EPA Substance Registry System: (+/-) 1-(4-BROMO-2 5-DIMETHOXYPHENYL)-2&(66142-81-2)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• RIDADR: 2811
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 66142-81-2(Hazardous Substances Data)

Usage

Definition

ChEBI: A 2-arylethylamine compound where the aryl moiety is 4-bromo-2,5-dimethoxyphenyl.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 27, p. 513, 1984 DOI: 10.1021/jm00370a014

InChI:InChI=1/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3

Upstream product

• 108536-18-1 β-dimethoxy-2,5 phenyl nitro ethylene 
• 14438-63-2 1-(2,5-dimethoxyphenyl)-2-nitroethanol 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 3600-86-0 2,5-dimethoxyphenethylamine 
• 98537-45-2 4-bromo-2,5-dimethoxy-β-nitrostyrene 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 

Downstream Products

• 1026161-82-9 N-[2-(4-Bromo-2,5-dimethoxy-phenyl)-ethyl]-4-phenyl-butyramide 
• 1404305-52-7 [¹¹C]Cimbi-36 
• 88441-07-0 1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane 
• 88441-05-8 1-(2,5-dihydroxy-4-cyanophenyl)-2-aminoethane 
• 88441-14-9 1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane 
• 88441-09-2 1-(2,5-dihydroxy-4-carboxyphenyl)-2-aminoethane 
• 88441-12-7 1-(2,5-dihydroxy-4-chlorophenyl)-2-aminoethane 
• 88453-16-1 1-(2,5-dimethoxy-4-cyanophenyl)-2-(phthalimidoamino)ethane 
• 88441-16-1 1-(2,5-dimethoxy-4-chlorophenyl)-2-(phthalimidoamino)ethane 
• 88441-11-6 4-(2-Amino-ethyl)-2,5-dimethoxy-benzoic acid 

Relevant articles and documents

Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes

An expeditious method is reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes.

5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism

The toxic hallucinogen 25B-NBOMe is very rapidly degraded by human liver microsomes and has low oral bioavailability. Herein we report on the synthesis, microsomal stability, and 5-HT2A/5-HT2C receptor profile of novel analogues of 25B-NBOMe modified at the primary site of metabolism. Although microsomal stability could be increased while maintaining potent 5-HT2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.

Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors.

The pharmacological profile of a series of (+/-)-2,5-dimethoxy-4-(X)-phenylisopropylamines (X=I, Br, NO(2), CH(3), or H) and corresponding phenylethylamines, was determined in Xenopus laevis oocytes injected with cRNA coding for rat 5-HT(2A) or 5-HT(2C) receptors. The efficacy and relative potency of these drugs were determined and compared to classical 5-HT(2) receptor agonists and antagonists. The rank order of agonist potency at the 5-HT(2A) receptor was: alpha-methyl-5-HT=5-HT>m-CPP>MK-212; at the 5-HT(2C) receptor the order was: 5-HT>alpha-methyl-5-HT>MK-212>m-CPP. All these compounds were full agonists at the 5-HT(2C) receptor, but alpha-methyl-5-HT and m-CPP showed lower efficacy at the 5-HT(2A) receptor. 4-(4-Fluorobenzoyl)-1-(4-phenylbutyl)piperidine (4F 4PP) was 200 times more potent as a 5-HT(2A) antagonist than at 5-HT(2C) receptors. Conversely, RS 102221 was 100 times more potent as a 5-HT(2C) antagonist, confirming their relative receptor selectivities. The phenylisopropylamines were partial agonists at the 5-HT(2A) receptor, with I(max) relative to 5-HT in the 22+/-7 to 58+/-15% range; the corresponding phenylethylamines had lower or undetectable efficacies. All these drugs had higher efficacies at 5-HT(2C) receptors; DOI was a full 5-HT(2C) agonist. 2C-I and the other phenylethylamines examined showed relative efficacies at the 5-HT(2C) receptor ranging from 44+/-10% to 76+/-16%. 2C-N was a 5-HT(2) receptor antagonist; the mechanism was competitive at the 5-HT(2A), but non-competitive at the 5-HT(2C) receptor. The antagonism was time-dependent at the 5-HT(2C) receptor but independent of pre-incubation time at the 5-HT(2A) receptor subtype. The alpha-methyl group determines the efficacy of these phenylalkylamines at the 5-HT(2A) and 5-HT(2C) receptors.