66142-81-2

Usage

Uses

Used in Pharmaceutical Industry:
(+/-) 1-(4-Bromo-2,5-dimethoxyphenyl)-2& is used as a pharmaceutical compound for its potential therapeutic effects. The presence of the 4-bromo-2,5-dimethoxyphenyl group may contribute to its biological activity, making it a candidate for the development of new drugs.
Used in Chemical Research:
(+/-) 1-(4-Bromo-2,5-dimethoxyphenyl)-2& is used as a research compound in the field of chemistry. Its unique structure allows scientists to study its properties and interactions with other molecules, which can lead to a better understanding of its potential applications and mechanisms of action.
Used in Material Science:
(+/-) 1-(4-Bromo-2,5-dimethoxyphenyl)-2& may also find applications in material science, where its unique structure and properties can be utilized to develop new materials with specific characteristics. This can include applications in areas such as sensors, catalysts, or advanced materials for various industries.

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

• 98537-45-2 4-bromo-2,5-dimethoxy-β-nitrostyrene 
• 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 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 
• 3600-86-0 2,5-dimethoxyphenethylamine 

Downstream Products

• 81255-55-2 2-(2-aminoethyl)-5-bromohydroquinone 
• 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 academic research and scientific papers

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.

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-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.

Synthesis of deuterium labeled phenethylamine derivatives

The synthesis of a series of five deuterium labeled phenethylamine derivatives, 4-bromo-2,5-[2H6]-dimethoxyphenethylamine (2C-B), 4-chloro-2,5-[2H6]-dimethoxyphenethylamine (2C-C), 2,5-[2H6]-dimethoxy-4-iodophenethylamine (2C-I), 2,5-[2H6]-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and 2,5-[2H6]-dimethoxy-4-n-propylthiophenethylamine (2C-T-7) from 1,4-[2H6]-dimethoxybenzene is described. The isotopically labeled compounds are used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays. Copyright

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.

Binding of Phenylalkylamine Derivatives at 5-HT1C and 5-HT2 Serotonin Receptors: Evidence for a Lack of Selectivity

Certain phenyalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors.It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors.The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other.An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = >0.9, n = 25) between 5-HT1C and 5-HT2 affinity.None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.