3-Methoxydextrallorphan

3-Methoxydextrallorphan

3-Methoxydextrallorphan is a chemical compound that belongs to the class of morphinan derivatives. It is structurally related to dextrallorphan, which is an active metabolite of the antitussive drug dextromethorphan.

Chemical Structure and Properties

3-Methoxydextrallorphan is characterized by the presence of a methoxy group at the 3-position of the dextrallorphan molecule. The chemical formula for 3-Methoxydextrallorphan is C18H25NO2, and it has a molecular weight of 287.40 g/mol.

The compound is a white crystalline powder that is soluble in organic solvents such as ethanol and chloroform but has limited solubility in water. The presence of the methoxy group influences its pharmacological activity and receptor binding affinity.

Pharmacology

3-Methoxydextrallorphan acts primarily as an NMDA receptor antagonist, similar to its parent compound dextrallorphan. NMDA receptors are a subtype of glutamate receptors that play a crucial role in synaptic plasticity and memory function. By inhibiting these receptors, 3-Methoxydextrallorphan can modulate excitatory neurotransmission in the central nervous system.

In addition to its NMDA receptor antagonism, 3-Methoxydextrallorphan may also interact with other receptor systems, including sigma receptors and opioid receptors, although its affinity for these receptors is generally lower compared to its action on NMDA receptors.

Potential Applications

Due to its NMDA receptor antagonistic properties, 3-Methoxydextrallorphan has been studied for its potential use in treating conditions associated with excessive excitatory neurotransmission, such as neuropathic pain, epilepsy, and neurodegenerative diseases. However, its clinical use is limited by potential side effects and the availability of more selective NMDA receptor antagonists.

Safety and Toxicology

The safety profile of 3-Methoxydextrallorphan has not been extensively studied in humans. However, as with other NMDA receptor antagonists, there is a potential risk of neurotoxicity and cognitive impairment with prolonged use or high doses. Animal studies have shown that NMDA receptor antagonists can cause neuronal damage in certain brain regions, particularly when administered at high doses.

Research and Development

Research on 3-Methoxydextrallorphan is primarily focused on understanding its pharmacological properties and potential therapeutic applications. Studies are ongoing to determine its efficacy and safety in various preclinical models of disease.

Also see

• Dextrallorphan
• Dextromethorphan
• NMDA receptor antagonist
• Morphinan
• Sigma receptor