'It hurts,' were the last words of a serial rapist and murder dubbed the 'ice pick killer' as he was executed by lethal injection for the death of a 20-year-old that went unsolved for two decades until he confessed.

Danny Paul Bible, 66, received the injection on Wednesday evening after unsuccessful appeals contended his multiple health issues made it likely his execution would be botched and cause him unconstitutional pain.

The US Supreme Court rejected a last-day appeal about an hour before he was put to death without apparent complications.

Asked by the warden if he had a final statement, Bible replied: 'No, sir.'

Danny Paul Bible, 66, received the lethal injection on Wednesday evening for a 1979 rape and murder in Houston that went unsolved for two decades until he confessed

His head was shaking slightly as the lethal dose of the sedative pentobarbital began. His attorneys said Parkinson's disease was among his ailments.

As the drug started to take effect, Bible started taking quick breaths, muttered at one point that it was 'burning' and that it 'hurts.'

His breaths then became snores and about a minute after the procedure began, all movement stopped.

Despite fears from his attorneys that a vein would not be found for the IVs, prison technicians had one needle inserted in his left hand three minutes after he was strapped to the death chamber gurney. The second IV was inserted in his right hand after another three minutes.

He stared intently at relatives of two of his victims who watched through a window a few feet from him, but never said anything to them.

He was pronounced dead at 6.32pm, about 15 minutes after the lethal dose started. The execution was the seventh this year in Texas, the country's most active death penalty state.

'Danny Paul Bible is as vile and evil a person that has ever drawn breath,' said Larry Lance, whose sister, Pam Hudgins, was among Bible's victims.

'We are glad to have witnessed him draw his last breath. I know he will burn in hell for eternity.'

He was pronounced dead at 6.32pm, about 15 minutes after the lethal dose started. The execution was the seventh this year in Texas, the country's most active death penalty state

Bible's guilt was not disputed, but his lawyers had proposed he be rolled in his wheelchair in front of a firing squad or be administered nitrogen gas to cut off oxygen to his brain until he stopped breathing.

Lawyers argued his deteriorating health left his veins unsuitable for IVs to be inserted.

If either of those alternatives wasn't possible — and state attorneys said neither was — Bible's lawyers said his punishment should be stopped.

He told detectives in Louisiana about four Texas killings and at least nine rapes, including five in San Jacinto County northeast of Houston

'His unique and severe medical conditions render lethal injection an intolerably cruel method of execution as applied to him,' attorney Nadia Wood told the high court.

His civil rights claim 'should not be barred simply because Texas has not authorized an alternative method of execution.'

Bible's appeal went to the Supreme Court after the 5th U.S. Circuit Court of Appeals on Tuesday refused his lawsuit seeking a reprieve, a restraining order and an injunction. Assistant Texas Attorney General Stephen Hoffman said in a court filing that the lawsuit was a 'meritless tactic' to delay his 'well-deserved execution.'

Lethal injection is the only execution method allowed in Texas and changing that would require approval of the state Legislature, which isn't scheduled to meet again until next year.

A handful of death penalty states allow nitrogen hypoxia, although the method hasn't been used. Three Utah inmates have been executed by firing squad, the most recent in 2010. Utah now allows that method if drugs for execution are unavailable.

Bible's lawyers also argued that severe tremors accompanying his Parkinson's disease would complicate insertion of needles. They warned of a problematic execution like ones in recent years in Ohio and Alabama.

Hoffman, the state attorney, noted that IVs had been used recently to draw blood from Bible as part of his medical care.

Bible was a drifter with a record of violence in several states when he was arrested in Fort Myers, Florida, in 1999 for a rape in Louisiana.

He told detectives in Louisiana about four Texas killings — including the death of a four-month-old boy — and at least nine rapes, including five in San Jacinto County northeast of Houston.

The four slaying victims included 20-year-old Inez Deaton, a friend of Bible's cousin who was found on the banks of a Houston bayou in 1979.

Investigators determined she had been raped and fatally stabbed with an ice pick.

The killing went unsolved for decades before Bible linked himself to the case, and a jury decided in 2003 that the man who became known in Houston as 'the ice pick killer' should die for the slaying.

His head was shaking slightly as the lethal dose of the sedative pentobarbital began. Pictured, the gurney sits empty in the death chamber in Huntsville, Texas

The three other killings all occurred in North Texas on the same day in May 1983. The victims were Bible's sister-in-law, Tracy Powers; her four-month-old son, Justin; and Powers' roommate, Hudgins.

Bible pleaded guilty to Hudgins' death and was sentenced to 25 year in prison. He served seven and was released to Montana in 1992 on a form of parole known as mandatory supervision.

At his trial for Deaton's slaying in Texas, Harris County prosecutors presented evidence of robberies, thefts, assaults and abductions, including the rape of an 11-year-old girl in Montana and his confessions to repeated sexual assaults of young girls from 1996 to 1998.

'Some criminals' actions are so heinous, they earn the label 'worst of the worst,' Harris County District Attorney Kim Ogg said.