China Manufacturer Wuhan Fortuna High Quality (+/-)-Narwedine CAS 1668-86-6 with Wholesale Price for sale
China Manufacturer Wuhan Fortuna High Quality (+/-)-Narwedine CAS 1668-86-6 with Wholesale Price for sale
China Manufacturer Wuhan Fortuna High Quality (+/-)-Narwedine CAS 1668-86-6 with Wholesale Price for sale
China Manufacturer Wuhan Fortuna High Quality (+/-)-Narwedine CAS 1668-86-6 with Wholesale Price for sale
China Manufacturer Wuhan Fortuna High Quality (+/-)-Narwedine CAS 1668-86-6 with Wholesale Price for sale

China Manufacturer Wuhan Fortuna High Quality (+/-)-Narwedine CAS 1668-86-6 with Wholesale Price Wholesale & Bulk

(+/-)-Narwedine is a 50/50 (racemic) mixture of two mirror-image forms of an organic compound. It is a crucial synthetic intermediate for producing galantamine, a medication for Alzheimer's disease.

Only one enantiomer, (-)-narwedine, leads to the active drug. The racemic mixture is used industrially because it can undergo dynamic kinetic resolution, a efficient process that favors the production of the desired, active enantiomer of galantamine during synthesis, making large-scale production feasible.


Items

Specifications

Results

Appearance

White or off-white powder

off-white powder

Heavy metals(Pb)

≤20ppm

20ppm

Loss on drying

≤1.0%

0.35%

Related substance(HPLC)

Single   impurities ≤1.0%

Total   impurities  ≤2.0%

0.58%

1.59%

Purity(HPLC)

≥98.0%

98.41%

Conclusion

The substance (+/-)-Narwedine   of batch No.JLXN20240401 complies   with the

Requirements of In House   Specifications.

 

(+/-)-Narwedine is a racemic mixture of a key organic compound that serves as a crucial intermediate in the chemical synthesis of galantamine, a medication used to treat Alzheimer's disease. The "(+/-)" symbol indicates that it is a 50/50 mix of two mirror-image forms (enantiomers) of the molecule.

Detailed Breakdown

1. The Name and Stereochemistry

  • (±) or (+/-): This prefix is chemical notation for a racemic mixture. It means the sample contains equal parts of the two enantiomers of the narwedine molecule.

    • Enantiomers are molecules that are non-superimposable mirror images of each other, much like your left and right hands. They are labeled as the (+)-enantiomer (which rotates plane-polarized light clockwise) and the (-)-enantiomer (which rotates it counterclockwise).

  • Narwedine: This is the name of the specific chemical compound. It has a defined molecular structure based on a fused ring system (a benzofuranone coupled with a cyclohexene ring).

So, (+/-)-Narwedine is a 1:1 mixture of (+)-Narwedine and (-)-Narwedine.

2. Chemical Structure and Relationship to Galantamine

Narwedine's primary importance lies in its relationship to the natural product galantamine (also known as galanthamine).

  • Galantamine is a biologically active compound originally isolated from certain daffodils and snowdrop bulbs. It is an acetylcholinesterase inhibitor, meaning it increases levels of the neurotransmitter acetylcholine in the brain, which is beneficial for treating the symptoms of mild to moderate Alzheimer's disease.

    Narwedine is structurally very similar to galantamine. It is essentially a precursor or synthetic intermediate. Through a specific chemical reaction (often a reduction), narwedine can be converted into galantamine.

The critical point is that only one of the two enantiomers in the racemic mixture is useful:

  • (-)-Narwedine is converted into (+)-galantamine, which is the naturally occurring, biologically active form of the drug.

    (+)-Narwedine is converted into (-)-galantamine, which is biologically inactive or much less active.

This relationship is why the synthesis and resolution of narwedine are so important.

3. Historical and Synthetic Significance: The "Narwedine Enone"

The synthesis of (+/-)-Narwedine and its subsequent conversion to galantamine was a landmark achievement in organic chemistry. The most famous synthesis was published by the Polish chemist Witold Jedrzejewski (also spelled Jędrzejewski) in 1972.

The key step in his synthesis produced an intermediate now famously known as the "Narwedine Enone" or "Jedrzejewski's Enone." This molecule is the immediate precursor to (+/-)-Narwedine.

The brilliance of this route is that the racemic Narwedine Enone can undergo a process called dynamic kinetic resolution during its conversion to galantamine. This is a sophisticated technique that, under the right conditions, can favor the production of the desired active enantiomer, (+)-galantamine, from the racemic starting material, making the synthesis much more efficient.

Why is (+/-)-Narwedine Important?

  1. Key to Industrial Synthesis: Because extracting galantamine from plants is inefficient and low-yielding, a reliable chemical synthesis is necessary to produce the drug on a commercial scale. The synthetic route through (+/-)-Narwedine provides a practical and scalable method.

  2. Illustrates Important Chemical Concepts: It is a classic example used to teach advanced organic chemistry concepts, including:

    • Racemic Mixtures and Enantiomers

      Asymmetric Synthesis

      Dynamic Kinetic Resolution - a powerful method for obtaining a single enantiomer from a racemic mixture.

  3. Historical Milestone: It represents a significant accomplishment in total synthesis, enabling the widespread availability of an important medicine.

Summary

FeatureDescription
IdentityA racemic mixture of the Narwedine molecule.
SignificanceA crucial synthetic intermediate for the production of the Alzheimer's drug, galantamine.
Key ConceptDemonstrates the importance of stereochemistry in drug development: only one enantiomer (from (-)-Narwedine) leads to the active drug.
ContextCentral to a famous industrial synthesis that relies on dynamic kinetic resolution to efficiently produce the desired single enantiomer of the final drug.


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