A sweeping bill that would create business-friendly rules for cryptocurrencies stalled in the Senate on Tuesday, a major blow to the crypto industry’s plans in Washington. The Senate voted 50 to 49 to block consideration of the Clarity Act, a high-profile piece of legislation shaped by crypto executives over months of negotiations with Congress and the White House. The bill passed in the House last year, but it has faced numerous delays in the Senate.

The vote was a stinging defeat for the industry that makes it unlikely the legislation will pass anytime soon — if ever. With the midterm elections coming up in November, the window to advance it is closing rapidly, despite more than $100 million in political spending by crypto companies. While many Republicans embraced the bill, Democrats largely opposed it. Many of their concerns centered on President Trump, who generated $1.4 billion from a network of crypto businesses last year. Democrats wanted stronger language to prevent the president and other public officials from using crypto to make money. Ultimately, no Democrat voted for the bill, leaving Republicans well short of the 60-vote threshold required to proceed. Several Republicans, including Senator Susan Collins of Maine and Senator Josh Hawley of Missouri, also cast “no” votes.

“All President Trump wants is for the Senate to give him time to crime, and I won’t support any piece of legislation that enables him,” Senator Ruben Gallego, Democrat of Arizona, said in a statement after the vote. “This legislation failed squarely because Republicans refuse to say no to the president.” The outcome was a bitter disappointment for crypto executives, who had made the Clarity Act their most important policy priority.

“Today’s vote was a failure of leadership,” Mason Lynaugh, executive director of the Stand With Crypto advocacy group, said in a statement. “Every day without action is a day that American innovation, jobs, and investments continue to be shipped overseas.”