HUNTSVILLE, Texas (AP) _ A defiant condemned killer who had tried to escape from death row at least twice spit out a handcuff key as lethal drugs began taking effect during his execution Tuesday.

The key fell from Ponchai Wilkerson's mouth onto the side of his face, where a shocked warden picked it up. Wilkerson was pronounced dead at 6:24 p.m. He had made no final statement.

Texas Department of Criminal Justice spokesman Larry Fitzgerald described the key as a universal handcuff and leg restraint key. It's unknown how Wilkerson got it.

Wilkerson, 28, had struggled with prison guards all day. He refused to leave his holding cell near the death chamber and guards had to use additional restraining bands to bind him to the gurney.

Hours before the execution, guards had to use a Mace-like gas on Wilkerson when he refused to leave his cell at the Terrell Unit prison near Livingston for the 40-mile trip west to the Walls Unit in Huntsville.

Wilkerson was convicted of the 1990 murder of Chung Myong Yi, 43, a Houston jeweler.

More recently, Wilkerson, armed with a sharpened piece of metal fashioned from a typewriter part, slipped from his death row cell Feb. 21 and with another inmate held a female prison guard hostage before surrendering. The guard was not harmed.

On Thanksgiving night 1998, Wilkerson and six other condemned prisoners fled their cells in another escape attempt. One of the convicts drowned after scaling a pair of tall fences that surrounded the Ellis Unit northeast of Huntsville. Wilkerson and five others gave up after guards began shooting at them.

Wilkerson was 11th convicted murderer to be executed in Texas this year and the first of two scheduled this week.