CARACAS—Venezuela is attempting to resell at a deep discount $5 billion of bonds it originally issued in December through a Chinese brokerage as it struggles to squeeze through a tightening cash crunch, according to investors who were offered the bonds.

The move is the country’s latest extraordinary move to raise funds after being shut out of the international debt market in recent years as its oil-rich socialist economy crumbles. But even bond funds that specialize in distressed debt are hesitating to buy in because of concerns about the irregularities surrounding the deal and questions from opposition lawmakers about its legality.

While much of Wall Street sees default as a matter of time, the offer could appeal to investors willing to take on the risk in exchange for potentially significant returns. Goldman Sachs Group Inc. recently paid $865 million for $2.8 billion in Venezuelan bonds in a transaction that drew widespread condemnation from rivals of embattled President Nicolás Maduro, who accused the New York bank of helping finance his increasingly authoritarian and isolated administration.

“It’s like they’re having a going-out-of-business sale,” said Russ Dallen, partner at the brokerage Caracas Capital Markets. “And that’s what buyers should be worried about. Either they’re really desperate or they’re just filling up their credit card with no plans of paying back.”

Haitong Securities USA, a unit of China’s Haitong Securities Co. , in recent weeks has been marketing the distressed debt to U.S. hedge-fund managers who specialize in buying emerging-market bonds, the investors who were offered the bonds said. Haitong had the title of underwriter when Venezuela issued the bonds to a state-owned bank in December.