Ephedra sinica

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Ephedra sinica
Chemical formula C22H29FO5
Molar Mass(g/mol) 392.461 
Melting Point(°C) 262
NFPA 704
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Uses

Primary

  • Pharm: WHO LEM component
  • Pharm: DHS AMF component

Natural occurrence

Hazards

Character

Production

Synthesis

To synthesize dexamethasone, 16β-methylprednisolone acetate is dehydrated to the 9,11-dehydro derivative.[1][2] This is then reacted with a source of hypobromite, such as basic N-Bromosuccinimide, to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring-opening reaction with hydrogen fluoride in tetrahydrofuran gives dexamethasone.

Testing

Purification

Storage

Disposal

See Also

References

  1. Arth, GE; Fried, J; Hoff, DR; et al (1958) "16-Methylated steroids. II. 16α-Methyl analogs of cortisone, a new group of anti-inflammatory steroids. 9α-Halo derivatives".
    Journal of the American Chemical Society 80(12); pp3161–3163. 
    DOI:10.1021/ja01545a063
  2. Taub, D; Hoffsommer, RD; Slates, HL; lWendler, NL (1958) "16β-Methyl cortical steroids".
    Journal of the American Chemical Society 80(16); pp4435. 
    DOI:10.1021/ja01549a095