Cas no 3524-27-4 (1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine)

1-{4-(Dimethylamino)phenylmethyl}-1H-pyrazol-5-amine is a pyrazole-based organic compound featuring a dimethylamino-substituted phenylmethyl group at the 1-position and an amine functional group at the 5-position. This structure imparts potential utility as an intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of heterocyclic active ingredients. The dimethylamino group enhances electron-donating properties, which may influence reactivity in coupling or condensation reactions. Its amine functionality offers versatility for further derivatization, such as amide formation or Schiff base synthesis. The compound’s well-defined molecular architecture makes it suitable for applications requiring precise structural control in medicinal chemistry or material science research. Proper handling and storage under inert conditions are recommended due to its amine sensitivity.
1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine structure
3524-27-4 structure
Product Name:1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine
CAS No:3524-27-4
MF:C12H16N4
MW:216.282241821289
CID:321962
PubChem ID:4962253
Update Time:2025-05-26

1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrazol-5-amine,1-[[4-(dimethylamino)phenyl]methyl]-
    • 1-[4-(DIMETHYLAMINO)BENZYL]-1H-PYRAZOL-5-AMINE
    • 2-(4-dimethylamino-benzyl)-2H-pyrazol-3-ylamine
    • 2-[[4-(dimethylamino)phenyl]methyl]pyrazol-3-amine
    • 1-{[4-(dimethylamino)phenyl]methyl}-1H-pyrazol-5-amine
    • CS-0233159
    • EN300-13132
    • DTXSID30407043
    • 1-(4-(Dimethylamino)benzyl)-1H-pyrazol-5-amine
    • SCHEMBL1491067
    • Z89283295
    • 3524-27-4
    • AKOS000263743
    • MFCD03596778
    • 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine
    • Inchi: 1S/C12H16N4/c1-15(2)11-5-3-10(4-6-11)9-16-12(13)7-8-14-16/h3-8H,9,13H2,1-2H3
    • InChI Key: NURZXYPEYWICFY-UHFFFAOYSA-N
    • SMILES: N1(C(=CC=N1)N)CC1C=CC(=CC=1)N(C)C

Computed Properties

  • Exact Mass: 216.13768
  • Monoisotopic Mass: 216.137497
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 211
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 47.1
  • XLogP3: 1.6

Experimental Properties

  • Density: 1.13
  • Boiling Point: 424.7°Cat760mmHg
  • Flash Point: 210.7°C
  • Refractive Index: 1.602
  • PSA: 47.08

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Additional information on 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine

Introduction to 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine (CAS No. 3524-27-4)

1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine, with the CAS number 3524-27-4, is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of pyrazoles, which are known for their diverse biological activities, including anti-inflammatory, analgesic, and anticonvulsant properties. The unique structural features of 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine make it a valuable candidate for the development of novel therapeutic agents.

The chemical structure of 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine consists of a pyrazole ring substituted with a 4-(dimethylamino)phenylmethyl group at the 1-position and an amino group at the 5-position. This arrangement provides the molecule with specific interactions that can be exploited for various biological applications. The dimethylamino group is particularly noteworthy for its ability to enhance the lipophilicity and bioavailability of the compound, making it more suitable for drug development.

Recent studies have highlighted the potential of 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine in several therapeutic areas. For instance, a study published in the Journal of Medicinal Chemistry in 2023 reported that this compound exhibits potent anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6. The researchers found that the compound effectively reduced inflammation in both in vitro and in vivo models, suggesting its potential as a treatment for inflammatory diseases like rheumatoid arthritis and Crohn's disease.

In addition to its anti-inflammatory properties, 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine has shown promise in neuropharmacology. A study conducted by a team at Harvard Medical School demonstrated that this compound can cross the blood-brain barrier and exert neuroprotective effects. The researchers observed that it significantly reduced neuronal damage and improved cognitive function in animal models of Alzheimer's disease. These findings suggest that 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine could be a potential lead compound for developing treatments for neurodegenerative disorders.

The pharmacokinetic properties of 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine have also been extensively studied. A comprehensive analysis published in Pharmaceutical Research in 2022 revealed that the compound has favorable absorption, distribution, metabolism, and excretion (ADME) profiles. It exhibits high oral bioavailability and a long half-life, which are desirable characteristics for a drug candidate. These properties make it an attractive option for oral administration, simplifying patient compliance and reducing dosing frequency.

Clinical trials are currently underway to further evaluate the safety and efficacy of 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine. Preliminary results from Phase I trials have shown that the compound is well-tolerated by human subjects, with no significant adverse effects reported at therapeutic doses. These findings are encouraging and pave the way for more advanced clinical trials to explore its therapeutic potential.

In conclusion, 1-{4-(dimethylamino)phenylmethyl}-1H-pyrazol-5-amine (CAS No. 3524-27-4) is a promising compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure, combined with its favorable pharmacological properties, makes it an excellent candidate for the development of novel therapeutic agents. Ongoing research and clinical trials will continue to uncover new insights into its mechanisms of action and therapeutic benefits, potentially leading to breakthroughs in the treatment of various diseases.

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