NASHVILLE, Tenn. (AP) — Tennessee executed Harold Wayne Nichols by lethal injection Thursday in Nashville for the 1988 rape and murder of Karen Pulley, a 20-year-old student at Chattanooga State Community College.

Nichols, 64, had confessed to killing Pulley as well as raping several other women in the Chattanooga area. Although he expressed remorse at trial, he admitted he would have continued his violent behavior had he not been arrested. He was sentenced to death in 1990.

“To the people I've harmed, I'm sorry,” Nichols said in his final statement. Before Nichols died, a spiritual adviser prayed over him in the execution chamber and the two recited together the 23rd Psalm and the Lord's Prayer. At several points, they teared up and their voices became strained. After the final “Amen,” the adviser, J.R. Davis, continued talking quietly, with Nichols nodding along.

“Go in peace, my friend. I love you,” Davis told Nichols.

Nichols was strapped to a gurney with a sheet pulled up to just above his waist and a long tube running from an adjoining room to an IV inserted on the inside of his elbow. There was a spot of blood near the injection site. At one point he took a very heavy breath and his whole torso rose up. He then took a series of short, huffing breaths that witnesses said sounded like snorting or snoring. Nichols’ face turned red and he groaned. His breathing then appeared to slow, then stop, and his face became purple before he was pronounced dead.

Nichols' sister, Deborah Perry, watched the execution from a witness chamber and cried quietly but did not speak.

Nichols’ attorneys unsuccessfully sought to have his sentence commuted to life in prison, citing the fact that he took responsibility for his crimes and pleaded guilty. His clemency petition stated “he would be the first person to be executed for a crime he pleaded guilty to since Tennessee re-enacted the death penalty in 1978.”

The U.S. Supreme Court declined to issue a stay of the execution on Thursday.

Pulley's sister, Lisette Monroe, had wanted to be present for the execution but became too overwhelmed, her husband and Pulley's brother-in-law, Jeff Monroe, told media afterwards. He read a statement that said the family “was destroyed by evil” the night Pulley was killed.

“Taking a life is serious, and we take no pleasure in it,” he said. “However, the victims, and there were many, were carefully stalked and attacked. The crimes, and there were many, were deliberate, violent, and horrific.”

In a recent interview, Lisette Monroe, said the wait for Nichols' execution has been “37 years of hell.” She described her sister as “gentle, sweet and innocent,” and said she hopes that after the execution she'll be able to focus on the happy memories of Pulley instead of her murder.

Pulley, who was 20 when she was killed, had just finished Bible college and was attending school in Chattanooga to become a paralegal, Jeff Monroe said.

“Karen was bubbly, happy, selfless, and looking forward to the life before her,” he said.

Nichols' attorney, Debbie Drew, also spoke after the execution, saying her client had turned his life over to God after speaking to Pulley's mother decades ago, shortly after he was sentenced. His execution “sent the message that no one can rise beyond the crimes they committed decades earlier and that redemption deserves no mercy,” she said.

Davis said after the execution that he had known Nichols for a decade as part of a prison men's group and believes that Nichols' remorse and spiritual transformation were genuine. Davis said Nichols committed “horrible crimes. But killing to teach people not to kill just doesn't make sense.”

Nichols had seen two previous execution dates come and go. The state earlier planned to execute him in August 2020, but Nichols was given a reprieve due to the COVID-19 pandemic.

Many states have had difficulty obtaining lethal injection drugs as anti-death penalty activists have put pressure on drug companies and other suppliers. Between the shortages and legal challenges over botched executions, some states have moved to alternative methods of execution including a firing squad in South Carolina and nitrogen gas in Alabama.

Including Nichols, a total of 46 men have died by court-ordered execution this year in the U.S.

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Corrects that Pulley was a student at Chattanooga State Community College.

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Reporter Adrian Sainz contributed from Memphis, Tennessee.