Dexter Drake Coffin III, 37-year-old Virginia heir to $19 million, had it all: yachts, fast cars, plenty of girlfriends and a jet-set lifestyle. He also used drugs extensively and has a lengthy criminal record.

Tuesday night, Coffin was returning to the Charlottesville jail where he is serving an 11-year sentence on prescription fraud convictions when he slipped away from two armed guards who were waiting for him outside a Harrisonburg, Va., hotel restroom.

In the few minutes before one of the officers became suspicious and entered the restroom to check on Coffin, he had walked out the back door and sped away in his wife's gold-colored Lincoln Continental.

Coffin, heir to part of the fortune from his family's invention of the flow-through tea bag, had persuaded the officers to stop at the Harrisonburg Sheraton Hotel for dinner after a court-allowed counseling session with his psychiatrist in the Shenandoah Valley town, according to police. His wife JoAnne, who had accompanied him to the doctor's office, was left behind with the officers.

"He is a very shrewd operator," Albemarle-Charlottesville jail administrator Michael McMahan said. "There is no doubt this was planned by him."

Police said yesterday they are continuing a multistate search for Coffin, but Albemarle County police Cmdr. Sylvia Bailey said, "He's more of a threat to himself than anybody else."

"It's an unusual situation, but he's an unusual guy," said James W. Updike Jr., the Bedford County commonwealth's attorney who prosecuted the prescription fraud cases against Coffin in December.

Coffin was convicted in a Bedford County court on 20 counts of illegally obtaining the prescription cough syrup Tussionex, Updike said.

"He pretended to be a doctor and called in prescriptions to himself," said Updike. "He was so addicted to this high-powered cough syrup that he couldn't get enough" of it.

Law enforcement officials said Coffin's criminal record spans more than a decade.

His first brush with the law came at age 24 when he sold a yacht that didn't belong to him, took the $115,000 and left for France, according to Charlottesville Assistant Commonwealth's Attorney Stephen B. Deaton.

Police said Coffin was arrested in Texas and Florida during the 1970s on numerous drug charges. They said he once worked on a road gang in prison pants and Gucci loafers.

Coffin, who ran a Charlottesville computer company, had been behind bars since October 1985 when he was arrested in Houston on charges of writing bad checks. He has not yet been tried on those charges, but in the intervening months was sentenced to a total of 11 years in prison for convictions of prescription fraud.

When he was arrested on those charges, police said Coffin told him that he was sick and had tried to get the drugs fraudulently from stores in several counties and cities. He also had used cocaine and other drugs, police said.

Sterling C. Proffitt, the chief of inmate services at the Albermarle-Charlottesville jail, said he has never met a prisoner quite like Coffin.

"There was always something: medical problems, dental problems, inmate rights," Proffitt said. "It was a request here, a request there, a request everywhere."

Proffitt said Coffin, who read law books voraciously and counseled other inmates on their legal rights, persuaded a judge to issue an order allowing him to make unlimited phone calls.

Proffitt said the jail officers who brought Coffin to his Harrisonburg psychiatrist, Dr. Robert Showalter, apparently didn't follow normal procedures when they stopped for dinner at the Harrisonburg hotel, about 50 miles from the jail.

"I can't say it's normal by any stretch of the imagination," said Proffitt. "There is an internal investigation going on now."

Other police officials said it was very likely that Coffin, who is so glib and friendly that they said it was easy to forget he is a prisoner, persuaded the officers to stop at the hotel.

Charlottesville police said they do not believe Coffin's wife was involved in the escape.

Court records in Charlottesville and Bedford County estimate Coffin's personal wealth to be $19 million, prosecutors said, but they believed that the trustees of his estate have blocked him from receiving a large portion of that money until criminal charges are cleared against him.

During an 1981 interview with The Washington Post, Coffin said, "I had the impression that the people who waited on us at the various clubs, at the lawn parties and in my house were put on earth to serve me. I figured there had to be a reason why I was receiving all these things [a motorboat at age 6, a horse at 13]. My conclusion was that I was special."