1 of 12 This undated photo provided by the Tennessee Department of Correction shows Billy Ray Irick, currently on death row at Riverbend Maximum Security Institution in Nashville, Tenn. Irick was convicted for raping and killing a 7-year-old girl in 1985, and is scheduled to be executed Thursday, Aug. 9, 2018. (Tennessee Department of Correction via AP)

1 of 12 This undated photo provided by the Tennessee Department of Correction shows Billy Ray Irick, currently on death row at Riverbend Maximum Security Institution in Nashville, Tenn. Irick was convicted for raping and killing a 7-year-old girl in 1985, and is scheduled to be executed Thursday, Aug. 9, 2018. (Tennessee Department of Correction via AP)

NASHVILLE, Tenn. (AP) — Tennessee carried out the execution Thursday of a man condemned for the 1985 rape and murder of a 7-year-old girl, marking the first time the state has applied the death penalty in nearly a decade.

Inmate Billy Ray Irick, 59, received a three-drug injection at a maximum-security prison in Nashville and was pronounced dead at 7:48 p.m., authorities said. He was convicted in 1986 in the death of Paula Dyer, a Knoxville girl he was babysitting.

The blinds between a witness room and the execution chamber were opened at 7:26 p.m. and Irick could be seen through glass windows strapped to a gurney, an IV stuck in his arm and leading back through the wall to a room hidden by a mirror-window, where someone administered the drugs. Asked if he had any words before the chemicals began flowing, Irick at first appeared to sigh and say “no.” But then he said, “I just want to say I’m really sorry and that, that’s it.”

Then the execution proceeded. A minute later, his eyes closed. Snoring and heavy breathing were heard. At 7:34 p.m., there was coughing, huffing and deep breaths. An attendant began yelling “Billy” and checked the inmate and grabbed his shoulder, but there didn’t seem to be any reaction. Minutes later, Irick let out a cough or choking sound, as his face turned dark purple. Then he appeared to stop making noise and was soon after pronounced dead.

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Hours earlier Thursday, the U.S. Supreme Court cleared the way for the execution, denying Irick’s request for a stay. But Justice Sonia Sotomayor issued a blistering dissent, recounting details from a recent state court trial of a case brought by inmates contesting Tennessee’s execution drugs.

Irick’s attorney, Gene Shiles, said his client was stoic in his last hours and accepted what would happen with “a lot of grace.” Irick ordered up a burger, onion rings and a soft drink for his last meal, and spoke with chaplains, Shiles said.

It was the first execution in Tennessee since December 2009, when inmate Cecil Johnson received a lethal injection for the 1980 killings of three people during a Nashville convenience store robbery. Since then, the state has endured legal challenges and difficulties finding execution chemicals, including its previous drug, pentobarbital.

On Monday, the state Supreme Court also had refused to block Irick’s execution, saying the lawsuit filed by inmates involving the execution drugs wasn’t likely to succeed. That case is continuing in a state appeals court.

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In a ruling late last month, Davidson County Chancellor Ellen Hobbs Lyle wrote that attorneys for 33 death row inmates, including Irick, didn’t prove that there is a substantially less painful means to carry out an execution or that the drugs the state planned on using would cause the inmate to be tortured to death.

Tennessee’s execution protocol called for use of midazolam as a sedative, the muscle-relaxer vecuronium bromide and then potassium chloride to stop the heart.

At question is whether midazolam is actually effective in rendering someone unconscious and unable to feel pain from the other two drugs. Federal public defender Kelley Henry said at trial that inmates were tortured to death, feeling like they were suffocating, drowning, and utterly confused.

Henry said in a statement Thursday night that witness observations suggest the midazolam didn’t render Irick fully unconscious, and those accounts were “indicative of pulmonary edema” from the drug.

Attorneys for the state have said the U.S. Supreme Court has upheld the use of midazolam in a three-drug series. Once Irick was dead, Attorney General Herbert Slatery said justice was delayed too long for the little girl killed and her family.

A small group of the victim’s family members watched in a separate viewing room. They opted against speaking at a news conference afterward.

“I hope tonight’s lawful execution in some way eases the heartache Paula’s family has lived with and brings a degree of closure to a chapter of their lives that has been indescribably difficult,” Slatery said in the statement.

In Nevada, the drug company Alvogen has sued to block use of midazolam in a stalled execution. Tennessee is one of 15 states siding with the state of Nevada against the company, though Tennessee is planning to use a version of the drug that is compounded, not directly purchased from a manufacturer.

Supporters and opponents of the death penalty turned out Thursday evening in places around the state.

The Tennessean newspaper reported death penalty opponents gathered around Tennessee in several churches and outside the prison before the execution. About 50 protesters were outside the prison, while others who support the death penalty also showed up as authorities kept the two groups apart.

The execution comes a week after Pope Francis revealed new Catholic church teaching that deems the death penalty “inadmissible” under all circumstances.

Prior to the pope’s emboldened stance against the death penalty, three Catholic bishops in Tennessee wrote Gov. Bill Haslam, telling him that “the death penalty contributes to the growing disrespect for human life.”

Haslam declined on Monday to intervene in Irick’s case.