California executed Clarence Ray Allen, its oldest condemned prisoner, by lethal injection early yesterday at San Quentin State Prison after last-ditch court appeals for a stay of execution failed.

Allen, who turned 76 on Monday and was legally blind, used a wheelchair and suffered from diabetes and chronic heart disease, had been sentenced to death for ordering the murders of three people in 1980 while serving a life sentence for murder in California's Folsom Prison.

The time of death was 12.38 a.m. (3.38 a.m. EST/0838 GMT) Two guards assisted a frail Allen, wearing an Indian headband, from a wheelchair shortly after midnight into San Quentin's cramped death chamber and he was gently scooted onto the gurney where he would die.

Allen breathed heavily as a team of guards restrained his arms and legs to the table and set about methodically preparing him for a lethal combination of drugs. He turned his head to witnesses he had requested attend his execution and appeared to say "I love you."

Five minutes passed from the time the first of two needles were inserted in Allen until a guard read his death sentence order at 12.19 a.m. Within minutes the lethal drugs were administered and Allen breathed heavily for a moment and then was motionless until he was pronounced dead.

Fifty witnesses, including members of Allen's family and members of the families of his victims, had squeezed into the small room housing California's death chamber, a small cell painted mint green. Few showed emotion, but a woman invited by Allen crouched three times and slumped against a wall, seemingly distraught.

Allen left behind a last statement in which he said goodbye to his death row neighbour of 20 years and his family. "My last words will be 'Hoka Hey it's a good day to die,'" Allen, of Native American ancestry, said in the statement.

Ahead of Allen's execution a prison spokesman described him as resigned to his fate but in good spirits after celebrating his birthday with his family.

Allen was served a last meal after 7 p.m. that included buffalo steak, an all-white-meat serving of Kentucky Fried Chicken, pan-fried bread, pecan pie and black walnut ice cream, and met with a Native American spiritual adviser at about 8 p.m., prison spokesman Eric Messick said.

Messick said Allen had never shown remorse for his crimes and Allen's final statement did not mention them.

California Assistant Attorney General Ward Campbell said Allen's execution was long overdue. "Allen received the justice he deserved," Campbell said.