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BOULDER, Colo. — Two Boulder County Sheriff’s Office deputies have been charged in the death of a man who was being taken to a detox center last year, the 20th Judicial District Attorney’s Office said Monday.

Deputies James O’Brien, 49, and Adam Lunn, 36, are being charged with manslaughter, a class four felony, in the death of 23-year-old Demetrius Shankling.

RELATED: Arrest affidavit for James O’Brien

RELATED: Arrest affidavit for Adam Lunn

Investigators determined the deputies killed Shankling by handcuffing him and putting him in a confined space of the transport van on his stomach.

On Sept. 9, Shankling was picked up by O’Brien and Lunn at Ninth Street and Canyon Boulevard in Boulder but was found unresponsive and not breathing when they arrived at the Addiction Recovery Center.

He was placed on life support but died 27 days later at a Denver hospital.

O’Brien and Lunn have been on paid administrative leave since Sept. 9.

The Boulder County Investigation Team with the aid of a Longmont Police Department detective launched an investigation that determined the deputies had been trained to not place a handcuffed person in that position.

An autopsy revealed Shankling died from positional asphyxia based on how he was positioned in the van. A forensic pathologist determined the manner of death to be homicide.

“I appreciate that Sheriff (Joe) Pelle made the decision to activate the Boulder County Investigation Team to conduct the investigation into this tragic incident,” District Attorney Michael Dougherty said in a statement.

“The members of the Team conducted a very thorough investigation, as did Coroner Emma Hall and her staff. When these difficult situations arise, it is important to have a shared and unwavering commitment to reaching the right result for the victim, law enforcement, and our community.”

O’Brien has been with the sheriff’s office since 1998 and Lunn since 2011.

“Mr. Shankling’s death is a tragedy to all involved, including Mr. Shankling, his family and the involved deputies,” Pelle said in a statement. “As part of our public safety mission, all deputies are responsible for safeguarding those in our care to the best of our ability and are accountable for the decisions and actions.”