DES MOINES, Iowa (AP) _ A federal drug agent, his wife and a businesswoman pleaded innocent to conspiracy and money-laundering charges involving hundreds of thousands of dollars invested in real estate and rare coins.

Drug Enforcement Administration Agent Dennis Harker, his wife, Mary Ann, and businesswoman Susan K. Terry entered their pleas Monday before a federal magistrate and were scheduled for trial Dec. 4.

Harker is a DEA agent in Miami; Ms. Terry owns SKT Construction Co. in West Des Moines. Harker formerly lived in West Des Moines and the trio have described themselves as high-school friends.

U.S. Magistrate Celeste Bremer freed the three, subject to a $100,000 penalty if they fail to appear for trial.

In addition to tax offenses, they are charged with conspiracy and with structuring bank deposits to keep them below $10,000.

A federal law designed to catch drug-money launderers requires banks to report deposits larger than $10,000.

The indictment doesn't refer to drugs.

The indictment alleges the Harkers had more than $1 million in transactions during years they reported only a fraction of that income for income tax purposes. It says Ms. Terry and Harker set up a company which funneled cash to real estate investments and rare coin transactions.

Harker faces up to 40 years in jail if convicted on all counts, while Ms. Terry faces up to 30 years. In addition to jail terms, the Harkers face Internal Revenue Service penalties if convicted on the tax charges.