Page last updated: 2024-12-07

1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane

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Description

You're asking about **1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane**, also known as **2C-B**.

**What is 2C-B?**

2C-B is a **psychedelic drug** that belongs to the **phenethylamine** class. It's known for its **hallucinogenic** and **empathogenic** effects, similar to other psychedelics like LSD and MDMA (ecstasy).

**Why is 2C-B important for research?**

2C-B has been the subject of significant research for several reasons:

* **Understanding the brain:** 2C-B's effects on the brain are complex. Research on 2C-B can help scientists understand the mechanisms of:
* **Serotonin receptors:** 2C-B is a potent agonist of serotonin receptors, particularly 5-HT2A and 5-HT2C. Understanding how it interacts with these receptors could provide insights into the brain's processing of sensory information, mood, and cognition.
* **Hallucinations and altered perception:** 2C-B's hallucinogenic properties offer a unique opportunity to study the neurological processes involved in altered states of consciousness.
* **Empathy and social behavior:** 2C-B's empathogenic effects, similar to MDMA, could be investigated to understand the neural basis of empathy and social bonding.
* **Therapeutic potential:** While still under investigation, 2C-B has shown potential for use in treating:
* **Depression and anxiety:** Some studies suggest it could have antidepressant and anxiolytic properties.
* **Addiction:** Research into 2C-B's effects on addictive behaviors is ongoing.
* **Terminal illness:** Its potential to alleviate anxiety and existential distress in patients with terminal illnesses is also being studied.
* **Safety and harm reduction:** Research is vital to understand the potential risks and adverse effects of 2C-B use, especially given its popularity as a recreational drug. This can inform harm reduction strategies and public health initiatives.

**Important Notes:**

* **2C-B is a Schedule I controlled substance in the US and many other countries.** This means its possession and use are illegal and subject to strict regulations.
* **Research on 2C-B is conducted under strict ethical and legal guidelines.** It's important to note that research should prioritize the safety and well-being of participants and adhere to all necessary regulations.

It's important to remember that research on 2C-B is complex and ongoing. While it holds potential for understanding the brain and developing new therapies, it's crucial to approach this research with caution and respect the legal regulations surrounding this substance.

1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane: structure given in first source; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID105432
CHEMBL ID8301
SCHEMBL ID1044696
MeSH IDM0162871

Synonyms (22)

Synonym
L000870
CHEMBL8301 ,
67460-68-8
(+/-)2-(2,5-dimethoxy-4-nitro-phenyl)-1-methyl-ethylamine
2-(2,5-dimethoxy-4-nitro-phenyl)-1-methyl-ethylamine(don)
2-(2,5-dimethoxy-4-nitro-phenyl)-1-methyl-ethylamine((r)-(-)-don)
(-)2-(2,5-dimethoxy-4-nitro-phenyl)-1-methyl-ethylamine
2-(2,5-dimethoxy-4-nitro-phenyl)-1-methyl-ethylamine
bdbm50014996
benzeneethanamine, 2,5-dimethoxy-alpha-methyl-4-nitro-
3fiv60666j ,
1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane
unii-3fiv60666j
2,5-dimethoxy-4-nitroamphetamine
SCHEMBL1044696
don (psychedelic)
(+/-)-1-(4-nitro-2,5-dimethoxyphenyl)-2-aminopropane
(+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane
benzeneethanamine, 2,5-dimethoxy-.alpha.-methyl-4-nitro-
J275.080E ,
DTXSID00874243
Q4596794
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (14)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.30000.00020.667710.0000AID5270
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.30000.00010.601710.0000AID5270
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki14.10000.00010.739610.0000AID3695
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki14.10000.00031.29679.2440AID3695
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Ki14.10000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Ki14.10000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.30000.00020.590910.0000AID5270
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Kd0.08510.00042.58328.5114AID6405
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.08510.00012.62198.5114AID6405
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.08510.00012.29338.5114AID6405
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.08510.00042.47358.5114AID6405
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.08510.00012.70068.5114AID6405
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.08510.00082.62148.5114AID6405
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.08510.02342.74218.5114AID6405
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.08510.00082.62148.5114AID6405
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID188584Number of rats responding out of 5 treated rats at a dose of 0.5 mg/Kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID3695Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytryptamine 1 receptor binding site by using [3H]-5-HT as a radioligand.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Central serotonin receptors as targets for drug research.
AID188586Number of rats responding out of 5 treated rats at a dose of 1 mg/Kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID188587Number of rats responding out of 5 treated rats at a dose of 1.5 mg/Kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID175416Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 0.5 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID6405Binding affinity at rat 5-hydroxytryptamine receptor.1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID5270Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) receptor using [3H]KET as a radioligand1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Central serotonin receptors as targets for drug research.
AID241440Inhibitory concentration against monoamine oxidase A in rat brain mitochondrial suspension2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling.
AID176716Dose at which the rats perform 50% appropriate drug -lever responding was determined1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID175419Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 1 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID175420Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 1.5 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID91217Compound tested for hallucinogenic activity in humans was reported; Value reported in (A)= Mescaline units1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.
AID5226Binding affinity against 5-hydroxytryptamine 2 receptor of rat frontal cortex using [3H]ketanserin radioligand1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (50.00)18.7374
1990's2 (33.33)18.2507
2000's1 (16.67)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.23

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.23 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.23)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]