More insight into Matthew Perry 's final moments are being uncovered. The Friends alum's last conversation with his assistant Kenneth Iwamasa —one of five people charged in connection to Perry's death —before being injected with his fatal dose of ketamine was revealed in a plea agreement Iwamasa made with the Department of Justice that was obtained by E! News Aug. 16.

On the day of Perry's Oct. 28 death, Iwamasa injected Perry with a dose of ketamine—a controlled substance known for its dissociative effects —around 8:30 a.m.

, the plea agreement alleged . The assistant gave him a second dose at 12:45 p.m.

while Perry watched a movie. Forty minutes later, Perry asked him for another injection and to prepare the hot tub, allegedly saying, “Shoot me up with a big one.” Shortly after the interaction, the Fools Rush In actor's third dose was administered, and Iwamasa left to run errands, per the filing.

When he returned, he allegedly found Perry dead, face down in the jacuzzi. E! News reached out to Iwamasa's attorney for comment but has not heard back. Perry and Iwamasa's final exchange isn't the only detail that’s come to light about the assistant's alleged involvement in the 54-year-old's death, which was ruled a drowning and drug-related accident—the result of "the acute affects of ketamine," according to the Los Angeles Medical Examiner.

The DOJ also alleged in an Aug. 15 press conference that Iwamasa had no prior medical training before injecting Perry with th.