Five men pleaded not guilty Monday to charges in a potentially precedent-setting case involving pornographic videos filmed in Santa Rosa and Escambia counties for a multimillion-dollar Web site.

Assistant State Attorney Russ Edgar said he expects one more arrest in the case.

Clinton Raymond McCowen of Navarre, Andrew Kevin Craft of Pace, Kevin Patrick Stevens of Pensacola, William Lee Beach of Milton and Thomas W. Dwyer of Pensacola face two charges each of racketeering.

Jane Marie Dreka of Lillian, Ala., faces the same charges, but on Monday was in jail in Baldwin County, Ala., charged with possession of crystal methamphetamine. She is scheduled to appear Aug. 14 before Circuit Judge Ron Swanson.

If convicted, the defendants each could face up to 60 years in prison.

McCowen � the site owner known as "Ray Guhn" � is also charged with money laundering. He could be looking at an additional 30 years in prison.

McCowen and Stevens were arrested last summer after a months-long investigation into Global Technology Productions, which did business as Ray Guhn Productions. The others were arrested later.

The business revolved around a Web site with some 5,000 subscribers who could view videos featuring group sex for $30 a month, the investigation showed. Prosecutors believe the site generated more than $1 million a year and had been in operation for about five years.

In addition to illegally producing and distributing pornography, prosecutors assert that paying the actors in the videos amounts to prostitution. They also say some of the participants were given illegal drugs before their performances.

The films were made at several homes in Pensacola and Pace, at hotels in Escambia County, along Interstate 10 and Interstate 110, in wooded areas and in other public places, investigators said.

About 100 local men and women are believed to have participated in the films.

Edgar agreed with defense attorneys who referred to this as a "case of first impression," meaning there have been no similar state cases to create a legal precedent.

"This combination of charges has not been presented before," Edgar said. "It has long been against the law to make and sell obscene material. It has long been against the law to engage in prostitution, and certainly, it has long been against the law to deliver controlled substances. But have we ever seen a case with all of these in combination? No."

Edgar successfully prosecuted a "case of first impression" in 2002 against Dr. James Graves of Milton. In that case, Graves was the first doctor to be convicted of racketeering in the sale of OxyContin prescriptions that resulted in the deaths of four patients.

Swanson accepted the five defendants' pleas at the Santa Rosa County Courthouse in Milton and set a hearing for Sept. 17 on the defendants' motion to have the trial moved to Pensacola. That's where the case was originally set, but the State Attorney's Office filed its charges in Milton.

Edgar said he chose Santa Rosa for the trial because, otherwise, he might have faced simultaneous trials with the same participants in different venues. That's because filming took place in Santa Rosa and Escambia counties, while the money laundering occurred in Navarre and at a bank in Fort Walton Beach, he said.

"We had three options in this case," Edgar said. "We could bring part of the case in Escambia, we could bring part of the case in Okaloosa County, or we could bring all of the case in Santa Rosa. The common denominator of the criminal acts alleged was Santa Rosa County."

Swanson set a Jan. 7 trial date. Some of the defense attorneys, however, said they're not sure that gives them enough time.

"We still have several depositions to take in this case," said Derek Brett, McCowen's lawyer. "We've had to reschedule the investigating officer. There have been other ones. We've had new state's witnesses added."

Swanson, however, thinks he is giving the defendants ample time.

"It is not even August, and I'm scheduling this for January," the judge said. "That's very reasonable. We're talking almost six months."