The family of an Alabama man killed in what is believed to be the longest recorded execution in U.S. history has accused the state of subjecting him to unnecessary cruelty in violation of his constitutional rights, according to a suit filed Wednesday.

Alabama killed Joe Nathan James Jr. on July 28 by lethal injection in an execution that lasted nearly three and a half hours, during which he was exposed to excessive pain and was prevented from speaking his last words, according to a complaint filed in the U.S. District Court for the Middle District of Alabama by James' brother Hakim James.

Joe Nathan James, 50, was punctured with a needle several times in multiple areas of his body during attempts to insert the two intravenous lines needed to administer the lethal drug into his veins, according to an autopsy report referenced in the complaint, which was filed by a team of Arnold & Porter attorneys working pro bono.

The suit brings claims under the Eighth and Fourteenth Amendments of the U.S. Constitution, as well as under state law and the Alabama Constitution. The complaint names as defendants Alabama Gov. Kay Ivey, Attorney General Steve Marshall, Alabama Department of Corrections Commissioner John Q. Hamm, Warden Terry Raybon, and six unnamed individuals who participated in the execution.

The complaint, which seeks unspecified monetary damages and attorney fees, also alleges that James, who was convicted for the 1994 murder of his ex-girlfriend, was deprived of his right to make his final speech, in which he planned to apologize to the victim's family and his own and to say a prayer.

Both the U.S. and the Alabama Constitutions have language banning "cruel or unusual punishment."

"Mr. James needlessly suffered severe pain during his more than three-hour-long execution," the suit says. "The execution team failed to execute Mr. James in a manner that comports with the U.S. Constitution, the Alabama Constitution, and applicable state law."

Case law developed in the Eleventh Circuit, which includes Alabama, has established that repeated and unsuccessful attempts to gain IV access during an execution can give rise to federal claims under the Eighth Amendment.

Under Alabama protocol, execution by lethal injection begins behind the scenes, with a team of technicians securing access to the inmate's veins. Then, once the IV is inserted, the curtains to the execution chamber are opened. The warden reads the death warrant aloud, then gives the inmate up to two minutes to make their last remarks. It's only then that a three-drug combination — midazolam to sedate and rocuronium bromide and potassium chloride to cause death — is let flow into the inmate's bloodstream.

Under typical medical standards, the first part of an execution should take no more than a few minutes. Some states mandate that prison officials abandon efforts to set an IV after more than an hour of failed attempts.

But on the day of James' execution, the procedure ended up taking more than three hours. He was strapped to the gurney shortly after 6 p.m. It took until 9:02 p.m. for the IV team to sufficiently insert needles into James' arms and required making incisions to expose his veins, which is against state protocol, the suit alleges.

When the curtains finally opened and Raybon read the death warrant to James, he was already unconscious, the complaint says. The warden held a microphone to James' lips and asked him if he wanted to say anything, but James was silent and unresponsive, according to the complaint. After the drugs were pumped into James' body, he was pronounced dead at 9:27 p.m.

"Mr. James was deprived of his rights to be mentally present for the reading of the death warrant, to provide last words, and to be cognizant of his punishment before the lethal drugs were administered," the suit says, alleging a violation of due process under the 14th Amendment.

Paige Sharpe, one of the Arnold & Porter attorneys representing James' family members, told Law360 the warden's actions were just a "pro forma" meant to show that the state's protocol was being followed.

"Officials knew that Mr. James was unconscious at the time," Sharpe said. "They just did it ... to check the box."

Since 2018, Alabama has botched the executions of three people.

In February 2018, the execution of Doyle Lee Hamm, whose blood vessels were compromised by cancer, was put off after the execution team spent nearly three hours trying to find a vein.

Last September, the state halted the execution of Alan Eugene Miller after nearly two hours were spent trying to set IV lines in his body. After Miller brought suit, Alabama agreed to kill him by nitrogen hypoxia — suffocation by breathing pure nitrogen — which the state approved as a method of execution on June 1, 2018.

And in November, Kenneth Eugene Smith was not executed after technicians were unable to insert an IV after nearly an hour and a half of attempts.

"Each of the individuals that Alabama failed to execute reported experiencing extreme pain from failed IV access attempts, and each of these individuals endured IV access attempts for less time than Mr. James," the suit says. "The only reason that the public knows what happened to these individuals is because they survived [the state's Department of Corrections'] efforts to execute them."

Anand Agneshwar, another Arnold & Porter lawyer for James' estate, told Law360 the suit filed Wednesday is about ensuring that Alabama does not cause unnecessary suffering for the people it executes.

"The hope is that this doesn't happen again to someone else," he said. "People can believe what they want about the death penalty, but it should be administered in a humane way."

Alabama could mount a defense based on qualified immunity, a legal doctrine that shields government officials working in their official roles from suits seeking monetary damages. This defense has been used in other suits challenging states' execution procedures.

Sharpe told Law360 the suit seeks to pierce through the opaqueness surrounding Alabama's execution protocol.

"We're seeking compensation for his family because that's the available remedy, but really, our goal in filing this lawsuit and working on behalf of Mr. James' family is to invite some transparency, to shed some light for Alabama," she said.

Representatives for the state's Department of Corrections did not immediately respond to requests for comment. Gina Maiola, a spokesperson for the Alabama governor, declined to comment on the allegations in the suit.

"To no surprise, news of this lawsuit went straight to the press," Maiola said. "Governor Ivey takes very seriously her lawful responsibility to carry out executions to obtain justice."

Counsel information for the respondents was not immediately available Wednesday afternoon.

The Estate of Joe Nathan James is represented by Anand Agneshwar, Paige Sharpe and Angelique A. Ciliberti of Arnold & Porter.

The case is The Estate of Joe Nathan James, Jr. v. Ivey et al., case number 2:23-cv-00293, in the U.S. District Court for the Middle District of Alabama.

--Editing by Alanna Weissman.

Update: This story was updated with quotes from a spokesperson for Alabama Gov. Kay Ivey.