An man convicted of murdering a woman after breaking into her apartment as she slept was put to death Thursday evening in Alabama in the nation’s fourth execution using nitrogen gas.

Alabama executed Demetrius Frazier for the 1991 murder of 41-year-old Pauline Brown two days before Thanksgiving.

The state of Alabama executed Demetrius Terrence Frazier by nitrogen gas Thursday evening for the rape and murder of Pauline Brown in Birmingham in 1991. Frazier, 52, the fourth person the state has executed by nitrogen gas,

ATMORE, Ala. (AP) — Alabama carries out the nation's 4th execution with nitrogen gas on a man convicted of a 1991 murder. The decision complicates a proposed sale of Jones' Infowars platform, and could spur divisions between families who sued Jones and won nearly $1.3 billion in Connecticut court cases and those who won $50 million in Texas courts.

Demetrius Frazier was executed Thursday in Alabama for the 1991 rape and murder of Pauline Brown, marking the fourth U.S. execution using nitrogen gas, the Associated Press reports. Frazier apologized to Brown’s family in his final words and criticized Michigan Governor Gretchen Whitmer for not intervening.

Demetrius Terrence Frazier is set to be executed with nitrogen gas for the rape and murder of 41-year-old Pauline Brown in Birmingham, Alabama.

A federal judge on Friday refused to stop what would be the fourth nitrogen gas execution in the U.S., saying the inmate had not proven his claims that the new method is unconstitutionally cruel and causes psychological terror.

Demetrius Terrence Frazier, 52, was convicted of the 1991 murder of 41-year-old Pauline Brown. Frazier raped and shot her after breaking into her Birmingham apartment, according to prosecutors. Frazier’s final words before being executed were,