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This section provides an overview for isoquinoline as well as their applications and principles. Also, please take a look at the list of 4 isoquinoline manufacturers and their company rankings. Here are the top-ranked isoquinoline companies as of December, 2024: 1.J&W Pharmlab.
Table of Contents
Isoquinoline (chemical formula: C9H7N) is a heterocyclic aromatic compound consisting of a benzene ring fused to a pyridine ring.
It is an isomer of the chemical compound quinoline, which is also called 2-azanaphthalene or 2-benzazine because of its structure. Many naturally occurring organic compounds containing nitrogen atoms, and alkanides, have the structural skeleton of isoquinoline. In a broad sense, isoquinoline refers to a variety of substances with this skeleton.
In Japan, isoquinoline is not designated as a substance under the Fire Service Law or the Poisonous and Deleterious Substances Control Law.
| Chemical Formula | C9H7N |
| English Name | Isoquinoline |
| Molecular Weight | 129.16 |
| CAS No. | 119-65-3 |
Isoquinoline and its derivatives are mainly used in the pharmaceutical field. Examples of specific uses include use in anesthetics, antihypertensives, and vasodilators.
Anesthetics
Chemicals such as quinisocaine are in practical use and exert local anesthetic effects by blocking nerve sodium channels.
Antihypertensives
Drugs such as quinapril are in practical use. This drug lowers blood pressure by disabling the enzyme that synthesizes angiotensin, a substance that induces high blood pressure.
Vasodilators
A drug called papaverine is used. This drug dilates blood vessels by acting on receptors such as acetylcholine receptors that exist in the smooth muscles controlling blood vessel and intestinal movements. Its main mechanism of action is by blocking the influx of calcium ions into vascular smooth muscle.
Other pharmaceutical uses include antimalarial, antifungal, and antiseptic.
Isoquinolines are also used as raw materials in the synthesis of dyes, and many substances such as isoquinoline dyes have an isoquinoline skeleton. Isoquinolines absorb the appropriate wavelength of light and are easily synthesized into a wide variety of derivatives, resulting in the synthesis of a wide variety of dyes.
In addition, isoquinolines are used as synthetic raw materials in the manufacture of pesticides for insecticidal applications. Isoquinoline has a tertiary amine moiety, which acts by inhibiting cholinesterase in insects and significantly increasing their acetylcholine levels.
Other uses of isoquinoline are in the manufacturing industry, where it is useful as a catalyst in the manufacture of polyimide film and as a corrosion inhibitor.
Isoquinoline has a melting point of about 26°C. When melted, isoquinoline is in a colorless oily state, but less pure samples may have a brown color. Like many nitrogen-containing compounds, it has a strong odor. Because of its pyridine ring, it is weakly basic, with a pKb of approximately 8.6.
Isoquinoline is insoluble in water but has high solubility in ordinary organic solvents such as ethanol, diethyl ether, and carbon disulfide. However, it can dissolve well in dilute acids because the nitrogen atoms in the molecule are protonated.
Isoquinolines have a structure that contains a nitrogen atom in the aromatic ring. Therefore, like pyridine, which also has a nitrogen atom in the aromatic ring, the carbon at position 2 is more susceptible to electrophilic substitution reactions.
It also has a higher electron density than the benzene and naphthalene rings, making it more reactive to electrophilic substitution reactions than these molecules.
Isoquinolines are obtained industrially by extraction from coal tar, but in the laboratory, there are various synthetic methods.
The first is synthesized by reacting benzylamine with glyoxal acetal using the Pomeranz-Fritsch reaction. This method is a very good way to obtain unsubstituted isoquinolines.
The second is the Pictet-Spengler reaction to synthesize tetrahydroisoquinoline derivatives from various benzylamine derivatives and aldehydes, followed by dehydrogenation.
*Including some distributors, etc.
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Kanto Chemical Co. Inc., founded in 1944 and headquartered in Tokyo, Japan, is a reagent manufacturer with overseas affiliates in other countries, including China, France, USA, Taiwan, and Malaysia. Its product portfolio includes analytical reagents, ionic liquids, Iodine compounds, ultra-pure chemicals, and water analysis kits. The company is also developing regenerative medicine and genetics reagents and has over 50,000 products. It has several certifications, including ISO 9001, acquired in 1994, making it the first Japanese company in the reagent industry. Other certifications are ISO 14001, ISO 13485, and ISO/IEC 17025.
TCI America (TCI) was founded in 1946 and is a worldwide manufacturer of specialty organic chemicals. The company produces organic laboratory chemicals as well as pharmaceutical, cosmetic, and functional materials. TCI’s product segments include Chemistry, Life Science, Materials Science, Analytical Chemistry, and Custom & Bulk. For materials science, the company manufactures battery materials, nanocarbon materials, and magnetic materials. For life sciences, the company produces antibodies, reagents, and chemicals for cancer research. The company produces HLC, NMR, various chemicals, and resins and media for analytical chemistry.
Merck, started in 1668 and based in Darmstadt, Germany, is a supplier of solutions and services for research, development, and manufacture of pharmaceutical and biotechnological drug therapies. The company serves the life science industry and has a broad portfolio of 300,000 products, including biopharmaceutical manufacturing, industrial microbiology, reagent, life science research, and water purification products. It is available in 66 countries, brings together six brands, and has several ISO certifications, including ISO 13485, ISO 14001, ISO 13485, and ISO 50001.
J&W Pharmlab was founded in 2002 and is headquartered in Pennsylvania, United States, as a custom synthesis, contract manufacturer, and outsourced contract R&D services. The company provides pharmaceutical services encompassing contract research and development (R&D), organic custom synthesis, process development, and the establishment of ground-breaking research chemicals. Regardless of the scale of the clients' bespoke synthesis project, whether it pertains to a small or large undertaking or whether it involves a research and development medicinal chemistry project or bulk manufacturing production, the company possesses the necessary resources to accommodate these requirements.
Ranking as of December 2024
Derivation Method| Rank | Company | Click Share |
|---|---|---|
| 1 | J&W Pharmlab |
100.0%
|
Derivation Method
The ranking is calculated based on the click share within the isoquinoline page as of December 2024. Click share is defined as the total number of clicks for all companies during the period divided by the number of clicks for each company.Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
Japan
|
2 | 100.0% |
