The worst "botched" execution in Death Row history left a dying killer "gulping for air for hours".
Joseph Wood was sentenced to death in Arizona for the murders of his estranged girlfriend and her dad.
But by the time he finally died, the murderer had been injected with 750mg each of midazolam, a sedative and hydromorphone, a narcotic, 15 times the amount called for in the state's execution protocol.
While he understandably received little sympathy from the family of his victims, his excruciating and prolonged death led to suggestions he may have endured a level of distress prohibited by the US constitution's ban on "cruel and unusual punishment".
Prison officials kept pumping drugs into Wood's system as his body refused to shut down.
The killer's filed an emergency appeal with the Supreme Court an hour into the botched procedure, writing in the motion: "He has been gasping and snorting for more than an hour. He is still alive."
The last-gasp appeal for denied by Justice Anthony Kennedy, with word reaching the Arizona State Prison Complex half an hour after Wood finally died.
Wood's drawn-out death was the third highly problematic prisoner execution in the US in 2014 after Dennis McGuire in Ohio and Clayton Lockett in Oklahoma.
All three executions used midazolam.
The most recent execution before Wood used pentobarbital, a barbiturate, a drug that acts as a central nervous system depressant.
The botched executions were put down to drug shortages prompted by Europe-led sales bans.
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It meant many states resorted to new, often experimental, drug cocktails.
Charles Ryan, the Arizona prisons department’s director, rejected claims that the execution was botched and said that the prison’s medical team verified several times that Wood was "comatose and never in pain".
Stephanie Grisham, then a spokeswoman for the Arizona attorney general's office and also a witness, backed up that claim.
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She said: "There was no gasping of air. There was snoring. He just laid there. It was quite peaceful."
But Dale Baich, one of Wood’s attorneys, said: "I’ve witnessed a number of executions before and I’ve never seen anything like this.
"Nor has an execution that I observed taken this long."
It was reported that he snorted or gasped 600 times during the excruciating execution.
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Wood, who was 55 when he died, was convicted of killing his estranged girlfriend Debra Dietz and her father Eugene Dietz in Tucson, Arizona, on August 7, 1989.
He shot the pair after his ex tried to end their relationship and get a protection order against him.
Debra's sister Jeanne Brown said: "What I saw today with him being executed, it is nothing compared to what happened on August 7, 1989.
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"What's excruciating is seeing your father lying there in a pool of blood, seeing your sister lying in a pool of blood."
Wood was the last person to be put to death in Arizona after the state temporarily suspended executions later in 2014.
In 2016 it was reported that Arizona had agreed to stop using the controversial drug midazolam in executions.
The following year, the drug's inventor opposed its use in executions.
Dr Armin Walser, who was part of the team that developed midazolam in the 1970s, said: "I didn't make it for the purpose of executing prisoners."
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