CARACAS -- Venezuela is attempting to resell at a deep discount $5 billon 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 Nicolas 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. Ltd., 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.

Unlike the bonds Goldman bought, the debt securities being shopped by Haitong aren't registered with the international organizations that settle such transactions, meaning they cannot be traded electronically, a risk that investors said was keeping them from buying them.

Spokesmen at Venezuela's finance and information ministries as well as Haitong Securities didn't respond to calls seeking comment.

Reeling from nearly two decades of economic mismanagement, Venezuela has had to resort to unorthodox financing methods through small and often times little-known institutions as large international banks veer away from Mr. Maduro's government.

Governments in the developing world typically plug funding gaps by issuing bonds through Wall Street firms and European banks that distribute the debt to bond-fund managers globally.

But Venezuela has lost access to that market in recent years. The economy has shrunk by an estimated 27% since 2013. The International Monetary Fund says inflation this year will hit 720%. Venezuela's central bank has stopped publishing basic economic indicators like balance of payments and gross domestic product since September 2015, making the country's capacity to pay a big guessing game for investors and credit rating firms alike.

Unable to tap debt markets, the government has turned to a strategy of issuing bonds directly to state-controlled entities that then try to resell the debt to foreign buyers for hard currency at bargain-basement prices.

The bonds picked up by Goldman Sachs in May were sold for 31 cents on the dollar, via U.K. broker Dinosaur Group.

Haitong is offering the additional bonds, which fall due in 2036, at an even deeper discount, the fund managers said.

The 2036 bonds were issued in December by Venezuela's government in a private placement to state-run Banco de Venezuela. At the time, the Finance Ministry had said the securities were earmarked as IOUs to be distributed to food and medicine importers that have ceased activity because Venezuela owes them billions of dollars in arrears.

But Mr. Maduro's political rivals also cried foul calling the bonds illegal because they were never approved by the opposition-controlled congress, also known as the National Assembly, which is calling the debt invalid.

"They are liquidating the nation's assets, indebting future generations, " said opposition lawmaker Angel Alvarado. Mr. Alvarado, who is a member of the Venezuelan congressional finance committee, said the legislature planned to debate the bond sale in Tuesday's legislative session.

Potential buyers fear that if Venezuela defaults, owners of the 2036 bonds wouldn't have the same claim as other bondholders because their bonds were issued at discount prices via an intermediary, Banco de Venezuela. They are also hesitant to buy the bonds because they haven't been registered with Euroclear or Depository Trust & Clearing Corp., the international securities settlement organizations that institutional investors use to trade electronically, one of the fund managers said.