69807-81-4

Usage

Uses

Used in Pharmaceutical Industry:
(1-METHYL-1H-PYRROL-2-YL)METHYLAMINE is used as an intermediate for the synthesis of various pharmaceuticals due to its ability to form derivatives with significant biological activity. Its incorporation into drug molecules can enhance their therapeutic effects and target specific biological pathways.
Used in Agrochemical Industry:
In the agrochemical sector, (1-METHYL-1H-PYRROL-2-YL)METHYLAMINE is utilized as a precursor in the development of agrochemicals, contributing to the creation of compounds that can improve crop protection and yield.
Used in Organic Synthesis:
(1-METHYL-1H-PYRROL-2-YL)METHYLAMINE is used as a reagent in organic synthesis, particularly for the production of complex molecules required in pharmaceutical research and development. Its role in this process is crucial for the advancement of new drug candidates and the exploration of novel chemical entities.

InChI:InChI=1/C6H10N2/c1-8-4-2-3-6(8)5-7/h2-4H,5,7H2,1H3

Upstream product

• 1192-58-1 N-methylpyrrole aldehyde 
• 55970-42-8 1-methyl-1H-pyrrole-2-carbaldehyde oxime 
• 1003-29-8 2-pyrrole aldehyde 
• 96-54-8 N-Methylpyrrole 
• 4513-94-4 1H-pyrrole-2-carbonitrile 
• 52160-51-7 (1-methyl-1H-pyrrole-2-yl)-methanol 
• 34884-10-1 1-methyl-1H-pyrrole-2-carbonitrile 
• 64230-41-7 1-methyl-1H-pyrrole-2-carboxamide 
• 37110-15-9 1-methylpyrrol-2-carboxaldoxime 

Downstream Products

• 26171-06-2 1-methyl-2-aminomethyl-pyrrolidine 
• 1018480-48-2 C₁₈H₁₇F₃N₄O₂S 
• 401908-38-1 1-(1-methyl-1H-pyrrol-2-ylmethyl)-3-phenethylthiourea 
• 769955-35-3 JAC₀₁₁₇₉-6 

Relevant academic research and scientific papers

Discovery of novel heteroarylmethylcarbamodithioates as potent anticancer agents: Synthesis, structure-activity relationship analysis and biological evaluation

A series of new analogs based on the structure of lead compound 10 were designed, synthesized and evaluated for their in vitro anti-cancer activities against four selected human cancer cell lines (HL-60, Bel-7402, SK-BR-3 and MDA-MB-468). Several synthesized compounds exhibited improved anti-cancer activities comparing with lead compound 10. Among them, 1,3,4-oxadiazole analogs 17o showed highest bioactivity with IC50 values of 1.23, 0.58 and 4.29 μM against Bel-7402, SK-BR-3 and MDA-MB-468 cells, respectively. It is noteworthy that 17o has potent anti-proliferation activity toward a panel of cancer cells with relatively less cytotoxicity to nonmalignant cells. The further mechanistic study showed that it induced apoptosis and cell cycle arrest through disrupting spindle assembly in mitotic progression, indicating these synthesized dithiocarbamates represented a novel series of anti-cancer compounds targeting mitosis.

Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: Comparison with effects on fatty acid amidohydrolase

A new series of arachidonic acid derivatives were synthesized and evaluated as inhibitors of the endocannabinoid uptake. Most of them are able to inhibit anandamide uptake with IC50 values in the low micromolar range (IC50 = 0.8-24 μM). ln general, the compounds had only weak effects upon CB1, CB2, and VR1 receptors (Ki > 1000-10000 nM). In addition, there was no obvious relationship between the abilities of the compounds to affect anandamide uptake and to inhibit anandamide metabolism by fatty acid amidohydrolase (FAAH; IC50 = 30-113 μM). This indicates that the compounds do not exert their effects secondarily to FAAH inhibition. It is hoped that these compounds, particularly the most potent in this series (compound 5, UCM707, with IC50 values for anandamide uptake and FAAH of 0.8 and 30 μM, respectively), will provide useful tools for the elucidation of the role of the anandamide transporter system in vivo.

Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors

In the present work, we have designed and synthesized a series of arachidonic acid derivatives of general structure I which have been characterized as highly potent and selective inhibitors of anandamide transporter (IC50 = 24-0.8 μM, Ki > 1000-5000 nM for CB1 and CB2 cannabinoid receptors and vanilloid VR1 receptor). Among them, N-(3-furylmethyl)eicosa-5,8,11,14-tetraenamide deserves special attention as being the most potent endocannabinoid transporter inhibitor (IC50 = 0.8 μM) described to date.

The reductive coupling of 2-cyanopyrroles: A study pertaining to the mechanism of formation of porphocyanines

2-Cyanopyrrole was found to form (2-pyrrolylmethene)-(2-pyrrolylmethyl)imine when treated with lithium aluminum hydride (LAH), followed by a mild work-up. A plausible mechanism of this reductive coupling was inferred from a series of experiments, including 27Al-NMR, deuteration experiments, and the reduction of variously substituted cyanopyrroles. The mechanism, a metal chelate mediated dimerization, may be the key to understanding porphocyanine synthesis via the LAH reduction of 1,9-dicyanodipyrromethanes.

Piperazinylalkyl Heterocycles as Potential Antipsychotic Agents

We recently reported on a series of pyrrole Mannich bases orally active in inhibiting the conditioned avoidance response (CAR) in rats.These compounds exhibit affinity for both D2 and 5-HT1A receptors, and some are noncataleptogenic.Such a profile suggest that they may be potential antipsychotic agents which lack the propensity for causing extrapyramidal side effects and tardive dyskinesias in humans.One of these compounds, 1--1-piperazinyl>methyl>-1H-pyrrol-2-yl>methyl>-2-piperidinone (RWJ 25730, 1), was chosen for further development but found to be unstable in dilute acid.In order to improve stability, we replaced the pyrrole methylene linkage to the piperazine ring with ethylene, employed ethylene and dicarbonyl as linkers between the lactam and the pyrrole ring, placed electron-withdrawing groups on the pyrrole ring, and substituted acyclic amide for lactam.In addition, we replaced the pyrrole segment with other heterocycles including thiophene, furan, isoxazole, isoxazoline, and pyridine.Generally, replacemcent of the N-methylpyrrole segment with thiophene, furan, isoxazoline, or pyridine afforded compounds equipotent with 1 in CAR, which were more stable in dilute acid.In the case of side chain or lactam modifications, CAR activity was significantly decreased or abolished, with the exception of 6.For the most part, the modifications to 1 resulted in the decrease or loss of D2 receptor binding.However, within this series, 5-HT1A receptor binding was greatly increased, with thiophene 40 exhibiting an IC50 of 0.07 nM.The CAR activities of pyrroles 6 and 12, thiophene 40, furans 44-47, isoxazolines 49 and 50, pyridine 54 coupled with their weak or nonexistent D2 binding and strong 5-HT1A binding suggest that they may be acting via a nondopaminergic mechanism or that dopaminergic active metabolites are responsible.Pyrrole 6 and furans 44 and 47 show promise as antipsychotic agents based on their CAR activity, receptor-binding profile, and solution stability.