Structure and stereochemistry of steroidal amine teratogens.

Studies of teratogenic steroidal alkaloids from Veratrum and Solanum have shown that those bearing a basic nitrogen atom in ring F, shared or unshared with ring E, with bonding capabilities alpha to the steroid plane may be suspect as teratogens. Examples of steroidal alkaloids which produce terata but, until recently, have been of uncertain structure include muldamine and the isomeric 3, N-diformylsolasodines. The correlation of their structures with the structure-terata relationship developed by Keeler and Brown is discussed. A brief introduction to teratogenicity is presented.