DUBAI, United Arab Emirates — Five Iranian tankers likely carrying at least $45.5 million worth of gasoline and similar products are now sailing to Venezuela, part of a wider deal between the two U.S.-sanctioned nations amid heightened tensions between Tehran and Washington.

The tankers’ voyage came after Venezuela’s socialist leader Nicolás Maduro already turned to Iran for help in flying in chemicals needed at an aging refinery amid a gasoline shortage, a symptom of the wider economic and political chaos gripping Latin America’s one-time largest oil producer.

For Iran, the tankers represent a way to bring money into its cash-starved Shiite theocracy and put its own pressure on the U.S., which under President Donald Trump has pursued maximalist campaigns against both nations.

But the strategy invites the chance of a renewed confrontation between the Islamic Republic and America both in the Persian Gulf, which saw a series of escalating incidents often involving the oil industry last year, and wider afield.

“This is like a new one for everyone,” said Capt. Ranjith Raja, an analyst who tracks oil shipments by sea at the data firm Refinitiv, of the gasoline shipments. “We haven’t seen anything like this before.”

All the vessels involved belong to Iranian state-owned or state-linked companies, flying under the Iranian flag. Since a pressure campaign on Iranian vessels began, notably with the temporary seizure of an Iranian tanker last year by Gibraltar, the country’s ships have been unable to fly flags of convenience of other nations, a common practice in international shipping.

The ships all appear to have been loaded from the Persian Gulf Star Refinery near Bandar Abbas, Iran, which makes gasoline, Raja said. The ships then traveled around the Arabian Peninsula and through the Suez Canal into the Mediterranean Sea, according to data collected from the ship’s Automatic Identification System, or AIS, which acts as a tracking beacon.

One of the vessels, the Clavel, listed its AIS destination as Caracas beginning May 12, according to log data from ship-tracking website MarineTraffic.com. The vessel later changed its destination as “TO ORDER” two days later, though the ship remains on a route that will see it leave the Mediterranean Sea and be in position to sail on to Venezuela.

Another tanker, the Forest, changed its AIS destination to “S. AMERICA TO ORDER” on May 14.

Three others, the Faxon, the Fortune and the Petunia, all appear on routes that could take them to Venezuela. Given the crushing U.S. sanctions imposed on Iran, also-sanctioned Venezuela appears to be the country that would have nothing to lose from accepting the shipments. Raja said Refinitiv had no data on any Iranian gasoline shipment ever going to South America before.

TankerTrackers.com, a website focused on the oil trade at sea, first reported the ships likely were heading to Venezuela.

The capacity of the five ships is some 175,000 metric tons. On the open market, the gasoline and product carried within them would be worth at least $45.5 million, though Iran likely reached a discounted, non-cash deal with Caracas given the circumstances the two nations face, Raja said.