Updated

Faced with grim testimony of poorly trained executioners operating in cramped, dimly lit quarters, a federal judge declared California's execution procedure unconstitutional.

The state's "implementation of lethal injection is broken, but it can be fixed," U.S. District Judge Jeremy Fogel ruled Friday in San Jose, extending a moratorium on executions in the nation's most populous state.

The decision is the latest in a nationwide challenge to lethal injection — the preferred execution method in 37 states — and came as Florida Gov. Jeb Bush suspended all executions there after a bungled execution this week. Missouri's injection method, which is similar to California's, was declared unconstitutional last month by a federal judge.

Fogel said the California case raised the question of whether the three execution drugs administered by the San Quentin State Prison are so painful that they "offend" the ban on cruel and unusual punishment. He said he was compelled "to answer that question in the affirmative."

The U.S. Supreme Court has upheld executions — by lethal injection, hanging, firing squad, electric chair and gas chamber — despite the pain they might cause, but has left unsettled the issue of whether the pain is unconstitutionally excessive.

California has been under a capital punishment moratorium since February, when Fogel called off the execution of rapist and murderer Michael Morales amid concerns that condemned inmates might suffer excruciating deaths.

Fogel found evidence that the last six men executed at San Quentin might have been conscious and still breathing when lethal drugs were administered.

A four-day hearing in September revealed that prison guards were inadequately trained to participate in executions. One prison official who was part of the execution team had been sanctioned for smuggling drugs into San Quentin.

Drugs were not properly accounted for, at times they weren't properly mixed and unused drugs were not returned to the prison's pharmacy. Executioners worked in the crowded chamber under dim lights.

Fogel ordered anesthesiologists to be on hand, or demanded that a licensed medical professional inject a large, fatal dose of a sedative instead of the additional paralyzing agent and heart-stopping drugs that are normally used. But no medical professional was willing to participate.

Morales, 47, of Stockton, raped and brutally beat a 17-year-old Lodi girl 25 years ago.

In Florida, Angel Nieves Diaz, 55, was put to death Wednesday for murdering the manager of a Miami topless bar during a holdup in 1979.

Medical examiner Dr. William Hamilton said Diaz's execution took 34 minutes — twice as long as usual — and required a rare second dose of lethal chemicals because the needles were inserted clear through his veins and into the flesh in his arms. The chemicals are supposed to go into the veins.

Hamilton, who performed the autopsy, refused to say whether he thought Diaz died a painful death.

"I am going to defer answers about pain and suffering until the autopsy is complete," he said. He said the results were preliminary and other tests may take several weeks.

Missing a vein when administering the injections would cause "both psychological and physical discomfort — probably pretty severe," said Dr. J. Kent Garman, an emeritus professor of anesthesia at the Stanford School of Medicine in California.

An inmate would remain conscious for a longer period of time and would likely be aware of increased difficulty breathing and pain caused by angina, the interruption of blood flow to the heart, Garman said.

Bush created a commission to examine the state's lethal injection process in light of Diaz's case, and he halted the signing of any more death warrants until the panel completes its final report by March 1.

The medical examiner's findings contradicted the explanation given by prison officials, who said Diaz needed the second dose because liver disease caused him to metabolize the drugs more slowly. Hamilton said that although there were records that Diaz had hepatitis, his liver appeared normal.

Executions in Florida normally take no more than about 15 minutes, with the inmate rendered unconscious and motionless within three to five minutes. But Diaz appeared to be moving 24 minutes after the first injection, grimacing, blinking, licking his lips, blowing and appearing to mouth words.

As a result of the chemicals going into Diaz's arms around the elbow, he had an 12-inch chemical burn on his right arm and an 11-inch chemical burn on his left arm, Hamilton said.

Florida Corrections Secretary James McDonough said the execution team did not see any swelling of the arms, which would have been an indication that the chemicals were going into tissues and not veins.

Florida got rid of the electric chair after two inmates' heads caught fire during executions in the 1990s and another suffered a severe nosebleed in 2000. Twenty people have been executed by lethal injection in Florida since the state switched from the electric chair in 2000.

Florida's death row has 374 inmates, while California's is the largest, with more than 650 inmates.