Salicylamide CAS No. 65-45-2

Product Description

Salicylamide is an aromatic amide compound known for its analgesic and antipyretic properties. Structurally, it is derived from salicylic acid, with the carboxylic acid group replaced by an amide group, resulting in the chemical formula C₇H₇NO₂ and an IUPAC name of 2-hydroxybenzamide. It appears as a white to slightly beige crystalline powder with a melting point of approximately 140–144°C and is slightly soluble in water but more soluble in alcohol and ether. Historically, salicylamide was used in combination with other compounds like caffeine and acetaminophen in over-the-counter pain relievers, though its use has diminished due to the popularity of more effective alternatives such as acetaminophen and ibuprofen. It acts by inhibiting prostaglandin synthesis, similar to aspirin, but is generally weaker in its effects. While considered safe at recommended doses, it may cause gastrointestinal irritation and allergic reactions in individuals sensitive to salicylates. Salicylamide is not classified as a strict NSAID due to the absence of a carboxylic acid group, but it shares similar mechanisms of action.

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Product Use & Characteristics

• Chemical Information:

  • IUPAC Name: 2-Hydroxybenzamide

  • Chemical Formula: C₇H₇NO₂

  • Molar Mass: 137.14 g/mol

  • Structure: Contains a benzene ring with a hydroxyl group (–OH) and an amide group (–CONH₂) in the ortho position.

  • Classification: Aromatic amide

• Physical Properties:

  • Appearance: White to slightly beige crystalline powder

  • Melting Point: ~140–144°C

  • Solubility: Slightly soluble in water; more soluble in alcohol and ether

  • pKa: ~9.5 (for the phenolic hydroxyl group)

• Chemical Properties:

  • Reactivity:

    • Amide groups can undergo hydrolysis to generate salicylic acid and ammonia.

    • Hydroxyl and benzene rings can participate in substitution reactions (e.g., nitration, sulfonation).

    • Under acidic or alkaline conditions, the molecular structure may change.

Uses of Salicylamide

• Medical Uses:

  • Analgesic and Antipyretic: Used to relieve mild to moderate pain such as headaches, muscle aches, dental pain, and menstrual cramps. Also reduces fever associated with illnesses like the common cold or flu.

  • Historical Use: Historically used in combination with other compounds (e.g., caffeine and acetaminophen) in over-the-counter pain relievers like PainAid and BC Powder.

  • Current Use: Less common today due to the popularity of other analgesics like acetaminophen and ibuprofen.

• Other Uses:

  • Organic Synthesis Intermediate: Used to synthesize other drugs or organic compounds, such as dyes and pesticides.

  • Cosmetics: Used as a preservative or antibacterial agent in some skin care products.

Safety and Side Effects

• Safety: Generally considered safe at recommended doses.

• Side Effects:

  • Potential gastrointestinal irritation.

  • Allergic reactions, especially in individuals sensitive to salicylates.

  • Long-term or high-dose use may cause liver damage.

  • Not recommended for individuals with salicylate allergies or certain kidney/liver conditions.

• Precautions:

  • Avoid combined use with anticoagulants (e.g., warfarin) to prevent increased risk of bleeding.

  • Pregnant and lactating women, as well as those with impaired liver and kidney function, should use with caution.

Other Information

• Metabolism: Rapidly absorbed from the gastrointestinal tract and metabolized in the liver, primarily by glucuronidation. Excreted mainly through the kidneys.

• Regulations: Listed as a drug or cosmetic raw material in many countries and must comply with relevant regulatory requirements. GMP (Good Manufacturing Practice) or relevant industry standards must be followed during use.

• Related Compounds:

  • Salicylic Acid: The precursor of salicylamide, with stronger anti-inflammatory and keratolytic effects.

  • Aspirin: An acetylated derivative of salicylic acid, widely used for antipyretic, analgesic, and anti-platelet aggregation effects.

• Research Progress: Salicylamide derivatives are being studied for the development of new anti-inflammatory drugs to reduce side effects and improve efficacy. They are also used in materials science to prepare functional polymer materials.

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