Two Bay Area pot retailers saw their owners strike deals with Canadian companies Monday, highlighting the financial edge Canada has gained in the marijuana industry since it became the first major economy to fully legalize cannabis in October.

Oakland’s Harborside, one of the nation’s largest dispensaries with 220 employees and some 100,000 clients, effected a complex transaction with Toronto’s Lineage Grow Co. The reverse takeover will allow Harborside to take the smaller company’s listing on the Canadian Securities Exchange, which has become a favored home for U.S. marijuana businesses.

“This is an opportunity for us to leverage the capital markets to raise money for more retail acquisitions, manufacturing work and working capital,” said Andy Berman, CEO of FLRish Inc., which operates Harborside’s dispensaries in Oakland and San Jose and its farm in Mendocino County. He will be CEO of the combined company, to be called Harborside Inc. “Canada is the place where you can have better access to the capital markets right now.”

Separately, the Apothecarium of San Francisco, which operates three dispensaries in the city and one in Las Vegas, agreed to sell itself for $118 million in cash and stock to TerrAscend, a Toronto cannabis producer licensed in Canada and some U.S. states.

Both transactions are subject to regulatory approval.

The deals show the dichotomy North American cannabis businesses face as they cross the 49th parallel. Legal in Canada, the industry is flush with capital, while in the U.S., where marijuana is still an illegal drug on the federal level, cannabis sellers pay state taxes in cash as they struggle to get basic banking services.

“The big trend is U.S. (cannabis) companies looking to Canada for money,” said Chris Walsh, founding editor of Marijuana Business Daily, which covers the industry. “They’re accessing capital in Canada they can’t access here. You can play in the public markets there, to tap money from anyone in the country investing in stocks.”

About 50 U.S. marijuana companies listed on the Canadian Securities Exchange last year, mainly through reverse takeovers similar to the Harborside deal, according to Marijuana Business Daily.

Christopher Barry, co-head of the cannabis practice group in Seattle at the law firm Dorsey & Whitney, said he and his partners have facilitated several dozen reverse takeovers between U.S. and Canadian marijuana companies, ranging in value from about $38 million to more than $1 billion.

“Cannabis companies with operations in the United States cannot list on U.S. stock exchanges,” he said. “If you want a liquid trading market to raise money, create a publicly traded stock to use for acquisitions and the like, the Canadian Securities Exchange is the only reasonable place you can do this.”

Canada’s other leading exchanges, the Toronto Stock Exchange and TSX Venture Exchange, will not accept listings from marijuana companies with U.S. operations, but will list Canada-only pot enterprises — as will the New York Stock Exchange and Nasdaq.

Lineage, valued at $23 million, technically bought Harborside, valued at $153 million, in an all-stock deal. But the owners of the Oakland company will wind up owning 81 percent of the combined company. Lineage has two dispensaries in Oregon, another in San Jose and a cannabis farm in Yolo County, employing about 50 people.

“Lineage was attractive because they came to the table with some cannabis assets,” Berman said.

Harborside Inc. plans to raise $53 million when the company is listed on the Canadian Securities Exchange, which it expects to happen after a couple of months of regulatory review.

In November, Harborside raised $26 million from investors led by Navy Capital Partners, an investment firm in New York with a focus on cannabis companies. The Oakland company has raised a total of $31 million since its founding 12 years ago. The company was profitable on sales of $45 million last year, Berman said.

Just two and a half years ago, Harborside avoided federal prosecution that aimed to shut down its operations. In 2016, Californians voted to allow the sale of recreational marijuana despite the federal ban.

The Apothecarium deal includes its retail shops in the Castro, Marina and South of Market neighborhoods, as well as a cannabis production facility and retail storefront in Nevada and Valhalla Confections, an edibles manufacturing business formed in 2014 by the Apothecarium’s owners.

“I never conceived of such an investment and exit when we started the company. This industry has changed by leaps and bounds,” said Apothecarium CEO Ryan Hudson. He started the company in 2011 with three first cousins and two family friends. This was his seventh business venture after six failed startups in the tech world, he said.

The Apothecarium offers hundreds of cannabis products, including local flowers and concentrates, chocolate truffle edibles, and coffees and teas. The dispensary had $45 million in revenue in 2018.

Hudson said the Apothecarium would continue to run under current management and retain its name, subject to local approvals.

“We’re not planning to go anywhere,” Hudson said. “Customer education and patient focus will remain our core goals and (TerrAscend wants) us to do more of that. We’re happy we found a partner we trust.”

Approximately 200 employees will receive stock options in the new parent company, he said.

“Canada is really pioneering the global marijuana industry,” Walsh said. “But momentum is building quickly (in the U.S.) with states like California, Colorado and Washington legalizing marijuana. When the (federal) laws change in the U.S., we will catch up quickly.”

Berman agreed. “The U.S. will wake up but I don’t know how soon,” he said.

Shwanika Naryana and Carolyn Said are San Francisco Chronicle staff writers. Email: shwanika.narayan@sfchronicle.com, csaid@sfchronicle.com Twitter: @shwanika, @csaid