Racepinephrine / Racemic adrenaline CAS No. 329-65-7

Product Description

Racepinephrine, also known as Racemic adrenaline, is a 1:1 mixture of the d- and l- enantiomers of epinephrine (adrenaline). It contains a catechol group and a secondary amine group, with the IUPAC name (±)-4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol. This synthetic sympathomimetic agent acts as a non-selective adrenergic agonist, stimulating both alpha- and beta-adrenergic receptors to cause vasoconstriction and bronchodilation. It is commonly used in aerosolized form to treat respiratory conditions like croup or bronchiolitis due to its local effects, though pure l-epinephrine is preferred for systemic use. The l-enantiomer is the biologically active form, while the d-enantiomer has weaker effects. Racepinephrine has a rapid onset when inhaled and a short duration of action (typically less than 2 hours). Possible side effects include increased heart rate, nervousness, tremors, and hypertension, so it should be used cautiously in patients with cardiovascular disease, hypertension, or hyperthyroidism.

Product Use & Characteristics

Properties and Characteristics

• Molecular Formula: C9H13NO3

• Molecular Weight: 183.2 g/mol

• IUPAC Name: 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

• Synonyms: Racepinephrine, (+-)-Adrenaline, Epinephrine, dl-, Racemic Epinephrine

• Physical Appearance: Odorless light brown or nearly white crystals

• Chemical Structure: Contains a catechol group (benzene ring with two hydroxyl groups at the 3 and 4 positions) and a secondary amine group (–NH–) on a side chain with a hydroxyl group.

Uses

• Medical Applications:

  • Respiratory Conditions: Used in aerosolized form for treating croup, bronchiolitis, and other upper respiratory conditions due to its local effects.

  • Adjunct Therapy: Sometimes used as an adjunct therapy for pulmonary hemorrhage.

  • Bronchodilation: Provides temporary relief of mild symptoms of intermittent asthma, including wheezing, tightness of chest, and shortness of breath.

• Inhalation Strategies:

  • On-Demand vs. Fixed Schedule: Studies have shown that on-demand inhalation is more effective than fixed-schedule inhalation in reducing hospital stay duration and the need for supportive treatments like oxygen supplementation and ventilatory support.

Pharmacology

• Mechanism of Action: Acts as a non-selective adrenergic agonist, stimulating both α- and β-adrenergic receptors.

  • α-Effects: Vasoconstriction, reducing mucosal edema.

  • β-Effects: Bronchodilation, increased heart rate.

• Onset and Duration: Rapid onset when inhaled, with a short duration of action (typically less than 2 hours).

Safety and Side Effects

• Possible Side Effects:

  • Increased heart rate (tachycardia)

  • Nervousness

  • Tremors

  • Hypertension

• Precautions: Should be used cautiously in patients with cardiovascular disease, hypertension, or hyperthyroidism.

Synthesis Methods

• Racemic Mixture: Comprises equimolar amounts of (R)-adrenaline and (S)-adrenaline.

• Production: Typically synthesized to include both d- and l-enantiomers, with the l-enantiomer being the biologically active form.