Cotarnine chloride

Catalog Number	ACM10018196
CAS Number	10018-19-6
Structure
Description	Cotarnine chloride is a covalent, active agent that is particulate in form. It has been shown to have hemostatic properties by forming a covalent bond with the fibers of blood vessels, as well as hydrogen bonds and hydrogen bonding. Cotarnine chloride also inhibits the formation of clots and thrombi by inhibiting platelet aggregation, which is mediated by adenosine diphosphate (ADP) and collagen. This drug also has anti-inflammatory properties due to its ability to inhibit an enzyme that catalyzes the conversion of arachidonic acid into prostaglandins.
Synonyms	7,8-Dihydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolinium chlorideCotarninium chlorideStypticin
Molecular Weight	255.7 g/mol
Molecular Formula	C12H14ClNO3
Canonical SMILES	C[N+]1=CC2=C(C3=C(C=C2CC1)OCO3)OC.[Cl-]
Harmonized Tariff Code	Switzerland: 29420090 - USA: 2942005000 - Slovakia: 2942000000 - UK: 2942000000 - China: 2942000000

Case Study

Multi-Component Synthesis and Transformation Method of Cotarnine Chloride

Voskressensky L G, et al. Chemistry of Heterocyclic Compounds, 2016, 52, 316-321.

Using cotarnine chloride as the starting material, a multi-component synthesis method of 1-ethynyl-substituted benzoxine was developed. When cotarnine chloride (1) was treated with silver phenylacetylide, 4-Methoxy-6-methyl-5-phenylethynyl[1,3]dioxolo[4,5-g]- isoquinoline (2) was synthesized. Additionally, the same reaction with methyl propiolate in acetonitrile resulted in a mixture of tetrahydro[1,3]dioxolo[4,5-i][3]benzazocine (3) and 5-methoxy-6-methylcarbonylvinyl-5-phenylethynyltetrahydro[1,3]dioxolo[4,5-g]isoquinoline (4).
Reaction of cotarnine chloride with silver phenylacetylide and alkynes
· A mixture of methyl propiolate (0.26 g, 3.10 mmol) or ethynyl methyl ketone (0.11 g, 1.60 mmol) and silver phenylacetylide (0.20 g, 0.96 mmol) was added to a suspension of cotarnine chloride (1) (0.20 g, 0.78 mmol) in MeCN (12 ml) with stirring. The reaction mixture was heated under reflux for 6 days, monitoring the progress by TLC using EtOH as the eluent.
· The solvent was evaporated under vacuum, and the resulting residue was purified by column chromatography on silica gel. Compounds 3 and 6 were isolated by eluting with an EtOAc-hexane mixture in ratios of 1:5 and 1:2, respectively, while compounds 5 and 7 were obtained using an EtOAc-hexane mixture in ratios of 1:3 and 1:1, respectively.

Cotarnine Chloride Used for the Synthesis of Tetrazolyl-Substituted Benzocines

Borisov R S, et al. Synlett, 2014, 25(07), 955-958.

Cotarnine chloride can be used to prepare pharmacologically relevant tetrazolyl-substituted benzocines via sequential azido-Ugi and alkyne-induced ring expansion reactions, such as a isoquinoline-tetrazoles and benzazocine-tetrazoles.
General synthesis procedures of isoquinoline-tetrazoles and azocines
· Isoquinoline-Tetrazoles: Cotarnine chloride (2) (1 mmol), isonitrile 3 (1.2 mmol), and NaN3 (1.2 mmol) were dissolved in a mixture of H2O and MeOH (1:5, 5 mL), and the solution was stirred at room temperature for 18 to 24 hours with TLC monitoring. Products 4a and 4b were separated using flash chromatography with EtOAc-hexanes varying from 1:50 to 1:10. Products 4c to 4i were obtained as precipitates from the reaction mixtures, filtered out, washed with cold MeOH (15 mL), and air-dried.
· Azocines: A solution of DMAD, methyl propiolate, or acetyl acetylene (1.2 mmol) was added to derivative 4a or 4c (1 mmol) in TFE (10 mL). The mixture was then stirred at 35 °C for 4 to 8 hours with TLC monitoring. The solvent was removed under reduced pressure, and the remaining residue was purified by crystallization from EtOAc-hexane to yield benzazocinetetrazole products 5a to 5d.

Custom Q&A

What is the chemical formula of Cotarnine chloride?

The chemical formula of Cotarnine chloride is C12H14ClNO3.

What is the molecular weight of Cotarnine chloride?

The molecular weight of Cotarnine chloride is 255.7.

At what temperature does Cotarnine chloride melt?

Cotarnine chloride melts at a temperature of 188-190°C.

In what form is Cotarnine chloride typically found?

Cotarnine chloride is usually found in solid form.

What color is Cotarnine chloride?

Cotarnine chloride is pale yellow to light yellow in color.

What is the stability of Cotarnine chloride?

Cotarnine chloride is hygroscopic, meaning it absorbs moisture from the air.

What are the storage conditions recommended for Cotarnine chloride?

Cotarnine chloride should be stored at -20°C in a freezer under an inert atmosphere.

What are the solubility properties of Cotarnine chloride?

Cotarnine chloride is slightly soluble in chloroform, methanol, and water.

What are the common uses of Cotarnine chloride?

Cotarnine chloride is an oxidative degradation product of the drug Noscapine.

What is another name for Cotarnine chloride?

Another name for Cotarnine chloride is Cotarninium Cation.

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