Sodium cyanate
Overview
Description
Sodium cyanate is an inorganic compound with the chemical formula NaOCN. It appears as a white crystalline solid and is the sodium salt of the cyanate anion. This compound is known for its use in various industrial and chemical applications due to its unique properties and reactivity .
Scientific Research Applications
Sodium cyanate has a wide range of applications in scientific research:
Biology: this compound has been studied for its potential therapeutic effects in treating sickle cell disease.
Medicine: It has been explored for its ability to counteract carcinogenic effects in the body.
Mechanism of Action
Target of Action
Sodium cyanate, an inorganic compound with the formula NaOCN, primarily targets hemoglobin in the body . It is known to carbamylate the terminal valine residues of hemoglobin . This carbamylation process is crucial for the compound’s therapeutic effects, particularly in the treatment of sickle cell disease .
Mode of Action
This compound interacts with its target, hemoglobin, through a process called carbamylation . This involves the addition of a carbamyl group (NHCO) to the terminal valine residues of hemoglobin . The carbamylation process alters the properties of hemoglobin, increasing its oxygen affinity . This change in oxygen affinity is believed to play a key role in the compound’s therapeutic effects .
Biochemical Pathways
The primary biochemical pathway affected by this compound involves the conversion of cyanate to ammonia and carbon dioxide . This reaction is facilitated by an enzyme known as cyanase . Cyanase converts cyanate to CO2 and NH3 in a bicarbonate-dependent reaction . This detoxification pathway helps to mitigate the toxicity of cyanate, which is harmful to all organisms .
Pharmacokinetics
It is known that this compound is soluble in water , which suggests that it could be readily absorbed and distributed in the body. More research is needed to fully understand the ADME properties of this compound and their impact on its bioavailability.
Result of Action
The carbamylation of hemoglobin by this compound results in increased oxygen affinity of the hemoglobin . This can have a significant therapeutic effect in conditions like sickle cell disease, where it helps to prevent the sickling of red blood cells . By increasing the oxygen affinity of hemoglobin, this compound helps to maintain the normal morphology of red blood cells, thereby mitigating the symptoms of sickle cell disease .
Action Environment
The action of this compound can be influenced by various environmental factors. For instance, the rate of cyanate reaction with water increases with temperature, concentration, and decreasing pH . Furthermore, this compound is stable to aqueous solution under the conditions of time, temperature, and concentration to which erythrocytes are most likely to be exposed in clinical application, except for its reaction with proteins and other biological materials .
Safety and Hazards
Future Directions
Sodium cyanate has been used in the treatment of sickle cell disease . It is also used as a raw material for organic synthesis, for pharmaceuticals, herbicides, and heat treatment of steel . Future research may focus on the production of isocyanate compounds directly from biomass . This could lead to the development of green polyurethanes with properties and performance comparable to fossil-based ones .
Biochemical Analysis
Biochemical Properties
Sodium cyanate is used to produce cyanic acid, often in situ . This approach is exploited for condensation with amines to give unsymmetrical ureas . Such urea derivatives have a range of biological activity . This compound is also an ideal nucleophile, and these nucleophilic properties make it a major contributor to the stereospecificity in certain reactions such as in the production of chiral oxazolidone .
Cellular Effects
This compound has been found to have effects on various types of cells and cellular processes. For instance, it has been found to have a role in sickle cell disease therapy . In aqueous solution, this compound decomposes to ammonia and sodium bicarbonate . The rate of cyanate reaction with water increases with temperature, concentration, and decreasing pH . Under the conditions of time, temperature, and concentration to which erythrocytes are most likely to be exposed in clinical application, this compound can be considered stable to aqueous solution, except for its reaction with proteins and other biological materials .
Molecular Mechanism
This compound exerts its effects at the molecular level through various mechanisms. One of the important physiological functions of cyanate is protein carbonylation, a non-enzymatic post-translational protein modification . Carbamylation reactions on proteins are capable of irreversibly changing protein structure and function, resulting in pathologic molecular and cellular responses .
Temporal Effects in Laboratory Settings
In laboratory settings, this compound has been observed to have changes in its effects over time. For instance, in a study on sickle cell disease, this compound was found to be stable to aqueous solution under the conditions of time, temperature, and concentration to which erythrocytes are most likely to be exposed .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. For instance, a study found that the i.p. injection of this compound (32 mg/kg) to mice once daily (five times a week) for a five-month period had no adverse effects .
Metabolic Pathways
This compound is involved in various metabolic pathways. Cyanate metabolism relies on the well-characterised enzyme cyanase, which catalyses the reaction of cyanate with bicarbonate to produce ammonium and carbon dioxide .
Transport and Distribution
It is known that this compound is used to produce cyanic acid, often in situ , suggesting that it may be transported into cells where it is needed.
Preparation Methods
Synthetic Routes and Reaction Conditions: Sodium cyanate can be synthesized through the reaction of urea with sodium carbonate at elevated temperatures. The reaction proceeds as follows: [ 2 \text{OC(NH}_2\text{)}_2 + \text{Na}_2\text{CO}_3 \rightarrow 2 \text{Na(NCO)} + \text{CO}_2 + 2 \text{NH}_3 + \text{H}_2\text{O} ] An intermediate, sodium allophanate, is observed during this process: [ \text{H}_2\text{NC(O)NHCO}_2\text{Na} \rightarrow \text{NaOCN} + \text{NH}_3 + \text{CO}_2 ]
Industrial Production Methods: Industrially, this compound is produced by heating a mixture of urea and sodium carbonate. This method is preferred due to its efficiency and the availability of raw materials .
Chemical Reactions Analysis
Types of Reactions: Sodium cyanate undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to form cyanic acid.
Substitution: It reacts with hydrochloric acid to produce cyanic acid and sodium chloride: [ \text{NaOCN} + \text{HCl} \rightarrow \text{HOCN} + \text{NaCl} ]
Condensation: Cyanic acid formed in situ can condense with amines to produce unsymmetrical ureas: [ \text{HOCN} + \text{RNH}_2 \rightarrow \text{RNHC(O)NH}_2 ]
Common Reagents and Conditions:
Oxidizing Agents: Mild oxidizing agents such as lead oxide can be used to prepare this compound from cyanides.
Acids: Hydrochloric acid is commonly used in substitution reactions.
Major Products:
Cyanic Acid: Formed during substitution reactions.
Unsymmetrical Ureas: Produced through condensation reactions with amines.
Comparison with Similar Compounds
Potassium Cyanate (KOCN): Similar in structure and reactivity to sodium cyanate, but with potassium as the cation.
Ammonium Cyanate (NH4OCN): Known for its role in the synthesis of urea through the Wöhler synthesis.
Sodium Cyanide (NaCN): Highly toxic and used in gold mining and electroplating.
Uniqueness of this compound: this compound is unique due to its relatively lower toxicity compared to sodium cyanide and its ability to form cyanic acid in situ, which is useful in various synthetic applications. Its role in biological systems, particularly in the treatment of sickle cell disease, also sets it apart from other cyanate compounds .
Properties
| { "Design of the Synthesis Pathway": "The synthesis pathway of Sodium cyanate involves the reaction of Sodium hydroxide and Potassium cyanate.", "Starting Materials": ["Sodium hydroxide", "Potassium cyanate"], "Reaction": [ "Mix Sodium hydroxide and Potassium cyanate in a 1:1 molar ratio", "Heat the mixture to a temperature of 150-200°C", "Maintain the temperature for 1-2 hours", "Cool the mixture and dissolve in water", "Filter the solution to obtain Sodium cyanate" ] } | |
CAS No. |
917-61-3 |
Molecular Formula |
CHNNaO |
Molecular Weight |
66.015 g/mol |
IUPAC Name |
sodium;cyanate |
InChI |
InChI=1S/CHNO.Na/c2-1-3;/h3H; |
InChI Key |
VXCSPBPIGBJXJR-UHFFFAOYSA-N |
Isomeric SMILES |
C(#N)[O-].[Na+] |
SMILES |
C(#N)[O-].[Na+] |
Canonical SMILES |
C(#N)O.[Na] |
| 917-61-3 | |
Pictograms |
Irritant |
Synonyms |
CyanicAcid, Sodium Salt ; Sodium Cyanate; Sodium Cyanate (NaOCN); Sodium Isocyanate; Zassol |
Origin of Product |
United States |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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