A double murderer took 11 minutes to be executed via a lethal injection drug never before used in the United States.
Mark Asay was killed at Florida State Prison in Raiford, Florida, for the 1987 murders of Robert Lee Booker and Robert McDowell.
His execution is now expected to pave the way for more death sentences to be carried out after states across the US struggled to obtain the drugs needed for lethal injections.
Asay was killed using etomidate which had been criticised by some as being unproven in an execution.
Etomidate replaced midazolam, which became harder to acquire after many drug companies began refusing to provide it for executions.
The 53-year-old, who was the first white man executed in Florida for killing a black man, was pronounced dead at 6.22pm.
Media witnesses said it took Asay around 11 minutes to die.
He had no last words.
Asay paid the ultimate punishment almost exactly four decades after his brutal crimes.
He had been drinking and playing pool with his brother Robbie and friend Bubba McQuinn when they went into downtown Jacksonville to look for prostitutes.
At one point Asay noticed his brother Robbie talking to a black man, Booker, from the window of his truck.
He became agitated and began shouting racial slurs.
McQuinn tried to calm him down but Asay shot Booker once in the stomach.
The victim fled but was later found dead in an alley from his injuries.
The trio continued to search for prostitutes, and met with Robert McDowell, a Hispanic transvestite known as 'Renee Torres'.
Asay, who had white supremacist tattoos, acted as lookout as Renee and McQuinn engaged in a sexual act.
But he then dragged Renee from the car and shot the victim six times.
The trial in 1987 was fraught with racial tensions - but a jury ultimately voted that Asay should be put to death.
During various appeals, he has argued that he didn't kill Booker and that he only got the white supremacist tattoos to avoid being attacked while in prison in Texas.
Since the Florida reinstated death sentences in 1976, 20 black men have been executed for killing white victims, according to the Death Penalty Information Centre.
Asay's final meal was fried pork chops, fried ham, French fries, vanilla swirl ice cream and a can of Coke.