LOS ANGELES — “Friends” actor Matthew Perry was experiencing an out-of-control ketamine addiction, injecting the drug six to eight times a day, before his accidental overdose death, prosecutors say.

Five people have been charged in connection with Perry’s death, including his personal assistant, Kenneth Iwamasa, and one of those accused of providing the drug, Dr. Salvador Plasencia.

In court documents filed Thursday, federal prosecutors accuse Plasencia of telling a patient that Perry was “too far gone and spiraling in his addiction” the week before he died but that he still offered to sell Perry ketamine through Iwamasa anyway.

Perry had been undergoing ketamine infusion therapy to treat depression and anxiety, but it was not the supervised therapy doses that killed him. His last session was more than a week before his death.

According to prosecutors, Perry had been seeking out unsupervised doses of the controlled substance and had developed an “out of control” dependence on it. Ketamine, an anesthetic with psychedelic properties, is a popular party drug that has recently been found to be a promising alternative treatment for some mental illnesses but carries serious medical risks.

Perry, 54, was found face down in the heated end of a pool at his Pacific Palisades home on Oct. 28. When he died, the levels of ketamine in his body were high — equivalent to the amount used for general anesthesia during surgery, according to the Los Angeles County Medical Examiner’s Office.

His assistant, Iwamasa, 59, pleaded guilty on Aug. 7 to one count of conspiracy to distribute ketamine causing a death and admitted having repeatedly injected Perry without medical training, according to prosecutors.

The court documents laying out Iwamasa’s plea agreement detail the depths of Perry’s addiction.

Iwamasa was accused of injecting Perry the day he died at 8:30 a.m. and again at 12:45 p.m. while Perry was watching a movie, the agreement said.

“Approximately 40 minutes later, Victim M.P. asked defendant to prepare the jacuzzi for Victim M.P. and told defendant, ‘shoot me up with a big one,’ referring to another shot of ketamine,” the document said.

After he injected Perry with the third shot in six hours, Iwamasa went to run errands, the documents say. He found Perry face down in the pool when he returned to the home, according to the plea agreement.

Iwamasa told authorities he began injecting Perry roughly a month before he died, after Perry was introduced to Plasencia around Sept. 30. He alleged that Plasencia sold Perry liquid ketamine, as well as ketamine lozenges, according to court documents.

Plasencia, 42, was arrested Thursday in Southern California and charged with one count of conspiracy to distribute ketamine. He pleaded not guilty in court Thursday afternoon. His lawyer did not respond to a request for comment.

Federal prosecutors said Plasencia taught Iwamasa how to administer the drug through intramuscular injection, even though Iwamasa had no medical experience or education.

Perry then instructed Iwamasa to stay in touch with Plasencia to buy more vials. The plea agreement recounts almost daily communications between Plasencia and Iwamasa to arrange more purchases in the next two weeks.

On Oct. 12, about two weeks before he died, Perry had a ketamine infusion with a doctor, but Plasencia was still contacted after the treatment for more, according to prosecutors. According to the plea agreement document, Plasencia agreed to meet at Perry’s home later that day and administered a “large dose of ketamine.”

Perry had a bad reaction to that dose, it said. His blood pressure spiked, his body began to “freeze up,” and he could not talk or move, prosecutors said. Plasencia left additional vials of ketamine for Perry at the house, despite Perry’s adverse reaction to it, prosecutors alleged.

According to prosecutors, the next day Perry instructed Iwamasa to obtain more ketamine from a different supplier, an acquaintance Iwamasa had previously gotten into contact with named Erik Fleming.

0 seconds of 3 minutes, 30 secondsVolume 90%

Fleming, 54, pleaded guilty on Aug. 8 to one count of conspiracy to distribute ketamine and one count of distribution of ketamine resulting in death.

Perry paid Plasencia — through his assistant — at least $55,000 for ketamine in the month before he died, Iwamasa’s plea agreement says. Fleming was paid about $12,000 in two separate deals, one of them just days before Perry died.

Another doctor was arrested Thursday and charged, and a third person has agreed to plead guilty in connection with Perry’s death.

Perry, who rose to fame on the beloved sitcom series “Friends,” was vocal about his addiction issues. He said in a 2022 interview on the “Q with Tom Power” podcast that he could not watch “Friends” because he could tell by his weight what substance he was abusing: alcohol, opiates or cocaine.

Perry wrote in his memoir that he “should be dead” after years of addiction and that his sobriety gave him purpose.

In 2013, Perry was given the Champion of Recovery award from the White House Office of National Drug Control Policy. The same year, he converted his Malibu residence into a sober-living home that operated for two years.

“I’ve said this for a long time: When I die, I don’t want ‘Friends’ to be the first thing that’s mentioned,” Perry said the year before he died. “I want [helping people] to be the first thing that’s mentioned. And I’m going to live the rest of my life proving that.”