67460-68-8

Basic information

• Product Name: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane
• Synonyms: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane;1-(2,5-Dimethoxy-4-nitrophenyl)-2-propanamine;1-Methyl-2-[4-nitro-2,5-dimethoxyphenyl]ethanamine;2,5-Dimethoxy-4-nitroamphetamine;2,5-Dimethoxy-α-methyl-4-nitrobenzeneethanamine;α-Methyl-2,5-dimethoxy-4-nitrobenzeneethanamine
• CAS NO: 67460-68-8
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 240.26
• Mol File: 67460-68-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 397.6°C at 760 mmHg
• Flash Point: 194.3°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 1.56E-06mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane(67460-68-8)
• EPA Substance Registry System: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane(67460-68-8)

Safety Data

• Hazardous Substances Data: 67460-68-8(Hazardous Substances Data)

Usage

General Description

1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane, also known as 2C-N, is a chemical compound belonging to the phenethylamine class. It is a potent psychedelic, and its effects on humans include visual and auditory distortions, as well as altered perception of time and space. 1-(2,5-Dimethoxy-4-nitrophenyl)-2-aminopropane is considered to be a hallucinogen and is illegal in many countries. It acts as a serotonin receptor agonist, specifically targeting the 5-HT2A receptor, and is thought to produce its psychoactive effects through this mechanism. Due to its potent effects and potential for abuse, it is classified as a controlled substance in many jurisdictions.

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

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

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 articles and documents

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.

The synthesis of some analogs of the hallucinogen 1 (2,5 dimethoxy 4 methylphenyl) 2 aminopropane (DOM)

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