LUCASVILLE, Ohio (AP) — Ohio executed a man Wednesday who fatally shot an adult bookstore security guard in 1994 at the end of a multistate crime rampage as witnesses of a second slaying victim of that rampage looked on intently.

Frederick Treesh received a single powerful dose of pentobarbital and was pronounced dead at 10:37 a.m. by Donald Morgan, warden of the Southern Ohio Correctional Facility in Lucasville.

Treesh was sentenced to die for killing Henry Dupree in Eastlake east of Cleveland on Aug. 27, 1994. He and a co-defendant were suspects in the shooting death three days earlier of Ghassan Danno, a Livonia, Mich., video store co-owner.

Prosecutors say Treesh, 48, and Benjamin Brooks robbed banks and businesses, committed sexual assaults, stole cars, committed carjackings and shot someone to death in a Michigan robbery during a series of crimes that also took them to Indiana, Iowa, Minnesota and Wisconsin.

“This is where drugs lead you,” Treesh, a former cocaine addict, said in a last statement.

He apologized for the death of Dupree, but said he wouldn’t say he was sorry to Danno’s family members, who sat a few feet away watching through a window. Treesh said he’d never been charged or tried in that slaying.

After a few more comments, Treesh said, “If you want me murdered, just say it.”

Treesh, of Waterloo, Ind., was the 50th inmate put to death by the state since it resumed executions in 1999.

The prison system said Treesh’s veins checked out beforehand, but executioners seemed to have a little difficulty inserting the IVs after Treesh entered the death chamber shortly after 10 a.m. A trickle of blood ran down Treesh’s right arm after one attempt, while the insertion on the left arm took a couple of attempts with the successful insertion on the inmate’s forearm.

Treesh was emotional after a phone call with his father Wednesday morning and tearful after a final visit with his attorney, according to prison officials. Shortly before 9 a.m. he ate the last of a hot fudge sundae from his requested meal the night before.

Treesh spoke a few times as the IV was inserted but his remarks were inaudible. He yawned shortly after the drug began flowing, then his mouth fell open, and he was still.

Danno’s sister-in-law said afterward that justice had been served.

“There’s one less sadistic killer in this world,” said Deanne Danno, who witnessed the execution. “He has no heart. He’s a soulless person that should never have been brought into this world.”

Gov. John Kasich denied Treesh clemency last week, following the recommendation of the state parole board, which ruled unanimously last month that the evidence showed Dupree was seated when shot and hadn’t shown any sign of being a threat to Treesh. The board also said Treesh’s decision to shoot a clerk in the face as he left the store suggests Treesh’s “murderous intent” when coming to the store.

Treesh and Brooks “gratuitously brutalized, humiliated and killed innocent people, most of whom, like Dupree, posed no real or perceived threat to them,” the board said.

Prosecutors said justice could be served and money saved by charging Treesh and Brooks only in Ohio.

Treesh’s attorneys described him as a cocaine addict who was high during the robbery and is deeply sorry for what happened.

“Hindsight, regret and remorse cannot turn back the clock and cannot return Mr. Dupree’s life,” they said in a petition for clemency. “What Fred can do and has tried to do is to help prevent others from making the same mistakes he did” by teaching them to avoid drugs.

His lawyers also alleged Treesh’s rights were violated during a prolonged interrogation as he was coming down from a drug high, which contributed to his death sentence. They also say Treesh suffers from health problems, including a seizure disorder, that raise concerns Ohio’s lethal injection process would cause him suffering amounting to cruel and unusual punishment.

Prosecutors contend Treesh intentionally murdered Dupree and tried to kill others, including police officers in pursuit.

“Treesh has never taken responsibility for his actions,” Lake County prosecutor Charles Coulson wrote. “Treesh still claims ‘the cocaine made him do it.'”

Coulson also noted that courts previously determined Treesh’s constitutional rights weren’t violated.

Treesh declined to be interviewed by the parole board.

The parole board cited Treesh’s refusal to be interviewed as evidence he has not grown or improved as a person in prison.

Treesh’s prison behavior is indicative of “a self-indulgent, petulant and immature individual,” the board said.

He was never prosecuted for the crimes in the other states, according to the Ohio Attorney General’s office.

Brooks, 45, of New Haven, Ind., pleaded guilty to avoid the death sentence and is serving 40 years to life in prison.

Ohio’s most recent execution was in November, when the state put to death Brett Hartman for the 1997 stabbing and dismemberment of an Akron woman.