67460-68-8

Usage

Uses

Used in Research Applications:
1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane is utilized as a research chemical for studying the effects of psychedelic substances on the human brain and their potential therapeutic applications. Its action as a serotonin receptor agonist, specifically targeting the 5-HT2A receptor, makes it a valuable tool in understanding the mechanisms underlying hallucinogenic experiences and their impact on cognitive and emotional processes.
Used in Pharmaceutical Development:
Although its use is restricted due to its potent effects and potential for abuse, 1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane may be employed in the development of new pharmaceuticals that target the serotonin system. Its agonistic properties could potentially be harnessed to create medications for the treatment of various psychiatric and neurological disorders, provided that safety and efficacy can be ensured through rigorous research and development.

InChI:InChI=1/C11H16N2O4/c1-7(12)4-8-5-11(17-3)9(13(14)15)6-10(8)16-2/h5-7H,4,12H2,1-3H3

Upstream product

• 2801-68-5 2,5-dimethoxyphenylisopropylamine 
• 42203-72-5 N-Acetyl-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropan 
• 18790-57-3 (E)-1,4-dimethoxy-2-(2-nitroprop-1-en-1-yl) benzene 
• 42311-16-0 (+/-)-N-acetyl-1-(2,5-dimethoxyphenyl)-2-aminopropane 
• 134040-27-0 2,5-dimethoxy-β-methyl-β-nitrostyrene 
• 93-02-7 2,5-dimethoxybenzaldehyde 

Downstream Products

• 111381-03-4 N-{2-[2,5-Dimethoxy-4-(piperidin-1-ylazo)-phenyl]-1-methyl-ethyl}-2,2,2-trifluoro-acetamide 
• 111381-02-3 N-[2-(4-Amino-2,5-dimethoxy-phenyl)-1-methyl-ethyl]-2,2,2-trifluoro-acetamide 
• 111381-04-5 N-trifluoroacetyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane 
• 24973-25-9 (+/-)-1-(2,5-dimethoxyphenyl)-2-aminopropane hydrochloride 
• 111381-01-2 N-[2-(2,5-Dimethoxy-4-nitro-phenyl)-1-methyl-ethyl]-2,2,2-trifluoro-acetamide 

Relevant academic research and scientific papers

Immunoassay for Phenethylamines of the 2C and DO Sub-Families

Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.

Immunoassay for Phenethylamines of the 2C and DO Sub-Families

Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.

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.

Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane

The serotonin (5-HT) receptor affinities and behavioral (discriminative stimulus) properties of a series of 4-substituted derivatives of 1-(2,5-dimethoxyphenyl)-2-aminopropanes (2,5-DMA) were investigated. The substituents at the 4-position included H, OMe, OEt, Me, Et, F, Br, I, and NO2. Substituent lipophilicities (π values) of these functionalities appear to have a minimal effect on either 5-HT receptor affinity or behavioral activity. Those derivatives previously found to be most potent in human studies possess significant affinity for 5-HT receptors. Furthermore, when rats trained to discriminate (±)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline were used, generalization was found to occur upon administration of the 4-substituted 2,5-DMA derivatives. Because a direct relationship exists between the ED50 values obtained from these discrimination studies and human hallucinogenic potencies, the discriminative stimulus paradigm, with DOM as a training drug, appears to be a useful tool for comparing the quantitative and qualitative (DOM-like) effects produced by certain hallucinogenic agents.