(3E)-3-[(2,4-Dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-2,3'-Bipyridine dihydrochloride
[CAS# 156223-05-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: (3E)-3-[(2,4-Dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-2,3'-Bipyridine dihydrochloride
• Synonyms: DMBX-anabaseine; DMXB-A; GTS 21
• Molecular Formula: C₁₉H₂₀N₂O₂.2(HCl)
• Molecular Weight: 381.30
• CAS Registry Number: 156223-05-1
• SMILES: COC1=CC(=C(C=C1)/C=C/2CCCN=C2C3=CN=CC=C3)OC.Cl.Cl

Properties

• Melting point: 216-217 °C (decomp)^*

^* Kem, William R.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

(3E)-3-[(2,4-Dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-2,3'-bipyridine dihydrochloride is a synthetic compound with promising pharmacological potential, particularly in the fields of neuropharmacology and medicinal chemistry. The compound is characterized by its unique bipyridine scaffold, modified with a methylene bridge linked to a dimethoxyphenyl group, providing a basis for its bioactivity and versatility in research applications.

The discovery of this compound stems from efforts to design novel small molecules capable of modulating neurotransmitter systems. The bipyridine core, a structure often associated with metal coordination and biological activity, was optimized to include additional functional groups to enhance receptor affinity and specificity. The introduction of the dimethoxyphenyl moiety was intended to improve lipophilicity and interaction with hydrophobic regions of target proteins.

One of the primary applications of this compound lies in its potential as a modulator of nicotinic acetylcholine receptors (nAChRs). Preliminary studies suggest that (3E)-3-[(2,4-dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-2,3'-bipyridine dihydrochloride exhibits selective binding to nAChR subtypes, making it a candidate for treating neurological disorders such as Alzheimer's disease, schizophrenia, and chronic pain. The specificity of the compound could minimize side effects commonly associated with non-selective ligands.

Another area of interest is its use in studying oxidative stress and neuroprotection. The bipyridine scaffold is structurally related to compounds known to interact with metal ions, such as iron and copper, which are implicated in oxidative stress pathways. This property positions the compound as a tool for exploring mechanisms of neurodegeneration and for developing antioxidant therapies.

In addition to its neuropharmacological potential, the compound has been investigated as a building block for creating complex chemical systems. Its bipyridine core allows it to serve as a ligand in coordination chemistry, facilitating the synthesis of novel metal-organic frameworks or catalytically active complexes. These systems could find applications in areas such as environmental remediation, catalysis, and advanced materials.

Despite its potential, (3E)-3-[(2,4-dimethoxyphenyl)methylene]-3,4,5,6-tetrahydro-2,3'-bipyridine dihydrochloride remains under early-stage evaluation. Further studies are required to fully characterize its pharmacokinetics, safety profile, and therapeutic index. Advances in synthetic and computational chemistry may aid in refining its structure to enhance its efficacy and reduce off-target effects.

References

2024-03-10. GTS-21 attenuates ACE/ACE2 ratio and glycocalyx shedding in lipopolysaccharide-induced acute lung injury by targeting macrophage polarization derived ADAM-17.
DOI: 10.1016/j.intimp.2024.111603

2023-04-17. Noninvasive ultrasound stimulation to treat myocarditis through splenic neuro-immune regulation.
DOI: 10.1186/s12974-023-02773-2

2023-02. Muscarinic and Nicotinic Acetylcholine Receptors in the Regulation of the Cardiovascular System.
DOI: 10.1134/s1068162023010211