Journal of Chemical Crystallography

, Volume 25, Issue 7, pp 393–400 | Cite as

Crystal and molecular structures of three modifications of the androgen dehydroepiandrosterone (DHEA)

  • Mino R. Caira
  • J. Keith Guillory
  • Luh-Chian Chang


The crystal and molecular structures of three forms of the androgen DHEA (dehydroepiandrosterone) have been determined by single crystal X-ray diffraction. They are: Form I, a polymorph crystallizing in space group P21 withZ=4; Form S1, a hydrate with composition DHEA. (1/4)H2O, space group C2,Z=8; and Form S4, a methanol half-solvate, DHEA. (1/2)CH3OH, space group C2221,Z=8. The A, B, and C steroid ring conformations adopted in the five crystallographically independent DHEA molecules are invariably: chair, 8β, 9α-half-chair, and chair, respectively, while the D ring conformation ranges from a 14α-envelope to a 13β, 14α-half-chair. In Forms I and S1, intermolecular hydrogen bonding is of the head-to-tail type with water molecules participating as donors in Form S1. In Form S4, DHEA molecules pack in head-to-head fashion, their hydroxyl groups being linked by hydrogen bonding to the solvent hydroxyl group. The hydroxyl H atoms of both DHEA and the included methanol are disordered, giving rise to an unusual linearly-propagating ‘flip-flop’ hydrogen bonding scheme.

Key Words

DHEA drug polymorphism 


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Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • Mino R. Caira
    • 1
  • J. Keith Guillory
    • 2
  • Luh-Chian Chang
    • 2
  1. 1.Department of ChemistryUniversity of Cape TownRondeboschSouth Africa
  2. 2.College of PharmacyThe University of IowaIowa City

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