STARKE, Fla. (AP) – A man convicted of murdering the manager of a topless bar nearly three decades ago was executed by injection Wednesday, appearing to grimace before dying 34 minutes after receiving the first of two doses of chemicals.

The manner of his death will likely rekindle the argument that Florida’s method of execution constitutes cruel and unusual punishment.

Angel Nieves Diaz, 55, was pronounced dead at 6:36 p.m., despite his protests of innocence and requests for clemency made by the governor of his native Puerto Rico. He appeared to move for 24 minutes after the first injection. His eyes were open, his mouth opened and closed and his chest rose and fell. He was pronounced dead 10 minutes after his last movement.

In most Florida executions, the prisoner loses consciousness almost immediately and stops moving within five minutes. The entire process usually takes about 15 minutes.

His final appeals to the U.S. Supreme Court challenged the chemicals used in the state’s procedure, but were rejected about an hour before his execution began. Defense attorneys have been unsuccessfully challenging Florida’s three-chemical method as unconstitutional cruel and unusual punishment, saying it results in extreme pain that an inmate cannot express because one of the drugs is a paralyzing agent.

Department of Corrections spokeswoman Gretl Plessinger said she doesn’t believe Diaz felt any pain, and his liver disease prompted the second dose of lethal chemicals.

“It was not unanticipated. The metabolism of the drugs to the liver is slowed,” Plessinger said.

But a spokesman for Floridians for Alternatives to the Death Penalty, called it a botched execution.

“They had to execute him twice,” Mark Elliot said. “If Floridians could witness the pain and the agony of the executed man’s family, they would end the death penalty.”

Diaz’s cousin, Maria Otero, said the family had no knowledge of any liver disease.

Gov. Jeb Bush, who rejected pleas for clemency from Puerto Rican officials including Gov. Acevedo Vilo and Senate President Kenneth D. McClintock, said in a written statement that the Department of Corrections followed all protocols.

“As announced earlier this evening by the Department, a preexisting medical condition of the inmate was the reason tonight’s procedure took longer than recent procedures carried out this year,” the statement said.

Diaz was executed for the Dec. 29, 1979, murder of Joseph Nagy, manager of the Velvet Swing Lounge in Miami. He was arrested in 1983 after his girlfriend told police he was involved in the killing. Diaz, who had a previous conviction for second-degree murder in Puerto Rico, and Angel “Sammy” Toro were charged with the slaying. Toro cut a deal with prosecutors and was sentenced to life in prison.

Moments before his execution, Diaz again denied killing Nagy.

“The state of Florida is committing a crime, because I am innocent,” Diaz said as he was strapped to a gurney. “The death penalty is not only a form of vengeance, but also a cowardly act by humans.”

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Associated Press reporter Lilliam Irizarry in San Juan, Puerto Rico, contributed to this report.

AP-ES-12-13-06 2205EST