page_title: Dantrolene
section_title: Synthesis
hierarchical_section_title: Dantrolene / Chemistry / Synthesis
caption_attribution_description: English: DOI: 10.1021/jm00317a011 US 3415821
context_page_description: Dantrolene sodium, sold under the brand name Dantrium among others, is a postsynaptic muscle relaxant that lessens excitation-contraction coupling in muscle cells. It achieves this by inhibiting Ca²⁺ ions release from sarcoplasmic reticulum stores by antagonizing ryanodine receptors. It is the primary drug used for the treatment and prevention of malignant hyperthermia, a rare, life-threatening disorder triggered by general anesthesia. It is also used in the management of neuroleptic malignant syndrome, muscle spasticity, and poisoning by 2,4-dinitrophenol or by the related compounds dinoseb and dinoterb.
  The most frequently occurring side effects include drowsiness, dizziness, weakness, general malaise, fatigue, and diarrhea.
  It is marketed by Par Pharmaceuticals LLC as Dantrium and by Norgine BV as Dantrium, Dantamacrin, or Dantrolen. A hospital is recommended to keep a minimum stock of 36 dantrolene vials totaling 720 mg, sufficient for a 70-kg person.
context_section_description: The original patent synthesis started with para-nitroaniline which undergoes diazotization followed by a copper(II) chloride catalyzed arylation with furfural (essentially a modified Meerwein arylation). This then reacts with 1-aminohydantoin to form the final product.
caption: Dantrolene synthesis:[13] Davis and Snyder; U.S. Patent 3,415,821 (1968 to Norwich Pharma Co).
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