An Ohio man convicted of the 1993 rape and murder of his girlfriend’s 3-year-old daughter was executed Wednesday, the state’s first execution since 2014.

The U.S. Supreme Court ruled against Ronald Phillips’ request for more time to combat his death sentence. His execution was carried out at 10:43 a.m. Wednesday morning after being allowed to meet with his family, USA Today reported. Phillips was 19 at the time of the killing and had argued he shouldn’t be eligible for the death penalty.

“Phillips argues that youth, like IQ, cannot be reduced to a number. But he also argues that the Eighth Amendment prohibits the execution of adults under age twenty-one,” State attorneys wrote in a court document filed Tuesday. “He cannot have it both ways; if age cannot make one eligible for death, it cannot make one ineligible for death.”

Several experts testified in court that the execution cocktail could cause Phillips an excruciating death. During Ohio’s last execution in 2014, the inmate had repeatedly snorted and gasped, leading many to question the effectiveness of the drugs. (RELATED: ‘Death Row Houdini’ Dodges 7 Executions But The Eighth One Sticks)

A federal court since approved the cocktail used on Phillips, however.

In his final statement issued by the corrections facility, Phillips expressed remorse for his actions.

“Sheila Marie did not deserve what I did to her,” he wrote. “I know she is with the Lord and she suffers no more. I’m sorry to each and every one of you that you lived with this pain all those years.”

For his last meal, Phillips asked for a large pizza with mushrooms and bell peppers, a bottle of Pepsi, a strawberry cheesecake, grape juice, and unleavened bread, FOX 8 reported.

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