Ira Freeman said a fax requesting several drugs came from Dr. Sandeep Kapoor on behalf of Smith's psychiatrist, Dr. Khristina Eroshevich, five months before Smith died of an accidental drug overdose of at least nine prescription drugs in a Florida hotel in early 2007.
"I called Dr. Kapoor," Freeman said. "I said, 'This is crazy. This is pharmaceutical suicide. The dosages are way out of whack.' I said I wouldn't fill it and no pharmacy in California would."
The hearing, which is in its second week, will determine whether Kapoor, Eroshevich and Smith's boyfriend-lawyer Howard K. Stern will stand trial for conspiring to illegally provide Smith with controlled substances. All three have pleaded not guilty.
Freeman said he had been dealing with Smith for years through his pharmacy, usually issuing prescriptions to her under the name of Michelle Chase, a pseudonym used to protect her privacy.
She always sent other people, including Stern, to pick up the prescriptions, Freeman said.
Under questioning by Deputy District Attorney Renee Rose, Freeman gave a long list of painkillers that had been prescribed to Smith over the years.
He said the one prescription he refused to fill was a request on Sept. 15, 2006, for six drugs, including opiates and the painkiller methadone.
Freeman said he recalled thinking that "if she got a hold of these medications, it could have fatal consequences."
He said he called a friend, a drug expert named Gregory Thompson, and asked him to speak with Eroshevich, who was with Smith in the Bahamas.
Prosecutors displayed an enlarged, hand-written letter sent by Eroshevich to Kapoor introducing herself and asking him for the six medications: Dilaudid, Lorazapam (also known as Ativan), Soma, Dalmane, Prexige and methodone.
Freeman said Eroshevich was seeking to prescribe Dalmane, a sleeping medication, at eight times the normal usage. She also wanted Soma, a muscle relaxant, in high dosage, he said.
During cross-examination by Kapoor's attorney, Ellyn Garofalo, Freeman said he had never had reason to question previous prescriptions by Kapoor.
Outside court, Garofalo said Kapoor did not know Eroshevich and simply forwarded the requests for medication because she was treating Smith in the Bahamas.
Kapoor kept prescribing drugs to Smith after that but in smaller doses, Freeman testified.