A Missouri inmate was put to death on Tuesday for a 2003 killing, becoming what is believed to be the first transgender woman executed in the US.
Amber McLaughlin, 49, previously known as Scott McLaughlin, was convicted of stalking and killing a former girlfriend before dumping the body near the Mississippi River in St Louis.
McLaughlin's fate was sealed on Tuesday when Republican Governor Mike Parson declined a clemency request.
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McLaughlin spoke quietly with a spiritual adviser at her side as the fatal dose of pentobarbital was injected. She then breathed heavily a couple of times, then shut her eyes.
She was pronounced dead a few minutes later.
"I am sorry for what I did," McLaughlin said in a final, written, statement. "I am a loving and caring person."
A database on the website for the anti-execution Death Penalty Information Centre shows that 1,558 people have been executed since the death penalty was reinstated in the mid-1970s.
All but 17 of those put to death were men. The centre said there are no known previous cases of an openly transgender inmate being executed. McLaughlin began transitioning about three years ago at the state prison in Potosi.
The clemency petition cited McLaughlin's traumatic childhood and mental health issues, which the jury never heard during her trial.
It cited severe depression that resulted in multiple suicide attempts, both as a child and as an adult.
The petition also included reports citing a diagnosis of gender dysphoria, a condition that causes anguish and other symptoms as a result of a disparity between a person's gender identity and their assigned sex at birth.
But McLaughlin's sexual identity was "not the main focus" of the clemency request, her attorney, Larry Komp, said.
In 2003, long before transitioning, McLaughlin was in a relationship with Beverly Guenther. After they stopped dating, McLaughlin would show up at the suburban St Louis office where the 45-year-old Guenther worked, sometimes hiding inside the building, according to court records.
Ms Guenther obtained a restraining order, and police officers occasionally escorted her to her car after work.
Ms Guenther's neighbours called police the night of November 20, 2003, when she failed to return home.
Officers went to the office building, where they found a broken knife handle near her car and a trail of blood.
A day later, McLaughlin led police to a location near the Mississippi River in St Louis, where the body had been dumped.
Authorities said she had been raped and stabbed repeatedly with a steak knife.
McLaughlin was convicted of first-degree murder in 2006. A judge sentenced McLaughlin to death after a jury deadlocked on the sentence.
Mr Komp said Missouri and Indiana are the only states that allow a judge to sentence someone to death.
A court in 2016 ordered a new sentencing hearing, but a federal appeals court panel reinstated the death penalty in 2021.
"McLaughlin terrorised Ms Guenther in the final years of her life, but we hope her family and loved ones may finally have some peace," Mr Parson said in a written statement after the execution.
McLaughlin began transitioning about three years ago but did not receive hormone treatments.
The Bureau of Justice Statistics has estimated there are 3,200 transgender inmates in the nation's prisons and jails.
Perhaps the best-known case of a transgender prisoner seeking treatment was that of Chelsea Manning, the former Army intelligence analyst who served seven years in federal prison for leaking government documents to Wikileaks until President Barack Obama commuted the sentence in 2017.
The Army agreed to pay for hormone treatments for Ms Manning in 2015.
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