(Bloomberg) — With Russian opposition leader Alexey Navalny lying in an induced coma just minutes from ’s office in Berlin, the German chancellor is at a loss over what to do about .

The German leader — a key conduit to the West for the Russian president — is frustrated that Putin has shown no flexibility on the case, according to two officials familiar with her thinking who asked not to be identified discussing internal deliberations.

Angela Merkel Exasperated by Putin as Navalny Lies in a Coma

© Bloomberg Russian Anti-corruption Campaigner Alexei Navalny Receives Treatment at Berlin’s Charite Hospital

Police vehicles outside Charite Hospital as Alexei Navalny undergoes treatment inside, in Berlin, on Aug. 24.

Photographer: Krisztian Bocsi/Bloomberg

While Merkel tends to choose her language carefully, her tone toward Russia has hardened. Less than two hours after doctors in Berlin determined that Navalny, a prominent Putin critic, had likely been poisoned, Merkel demanded Putin “fully investigate this act as a matter of urgency” and identify those involved.

The speed with which she responded, according to the officials, was meant to send the signal to the Kremlin how seriously Merkel takes the matter. It tops a list of grievances that includes a murder in broad daylight in a Berlin park last summer and a 2015 cyberattack on the Bundestag, Germany’s lower house.

A Russian speaker who grew up in East Germany, Merkel has sought to leverage her position to open a channel with Putin, who served as a KGB lieutenant in Dresden in the years before the Berlin Wall collapsed in 1989.

Limited Leverage

The issue is that whatever sway she might have had appears to have largely faded. All the condemnation over Russia’s annexation of Crimea did not change the facts on the ground even though Putin was excluded from the Group of Eight.

And with U.S. President Donald Trump mired in a re-election campaign and Merkel’s long tenure in power coming to an end next year, Putin may well feel emboldened to act without fear of retribution.

His chief spokesman, Dmitry Peskov, continued to brush off her calls for an investigation Wednesday, calling assertions Navalny was poisoned “hasty.”

“How can we talk about a poisoning when there’s no poison” yet identified, he asked on a conference call. The opposition leader was flown to Berlin on Saturday after he’d fallen ill on a flight to Moscow on Thursday.

The speaker of the lower house of Russia’s parliament, Vyacheslav Volodin, suggested the whole episode may be “a provocation by Germany and other members of the EU aimed at creating more allegations against our country.”

A medical team at Berlin’s Charite hospital said on Monday that they had found traces of a cholinesterase inhibitor, a possible nerve agent, even if the specific substance hadn’t yet been identified.

Get Tough

At least one lawmaker in Merkel’s party, Michael Brand, called on the European Union and Germany to take “tougher measures to stop the increased number of state-sponsored killings.” Other officials in Berlin said it was too early to talk about sanctions.

The U.S. threatened tough countermeasures if the poisoning is confirmed, according to the Russian Foreign Ministry. U.K. Prime Minister Boris Johnson also called for a “full, transparent investigation.”

Peskov said there was “no reason at all” for a worsening of relations with the West as a result of the case. Asked about Merkel’s frustration with Putin, he said the Kremlin relies on official statements from Germany on ties.

Others in Moscow aren’t so sanguine. “Of course this is very bad for Russia’s relations with Germany and Europe,” said Andrey Kortunov, director of the Kremlin-founded Russian International Affairs Council.

Read More: Putin, Poison and the Importance of Alexey Navalny: QuickTake

Anti-Kremlin protests in Russia’s Far East and a popular uprising against Belarus’s Putin-backed leader, Alexander Lukashenko, could prompt the West to see the poisoning of a prominent opposition figure “as a sign that Putin is losing control of the situation,” he said.

Should frictions reach a peak, projects such as the Nord Stream 2 gas pipeline under the Baltic Sea, which Merkel’s government has defended in the face of forceful criticism from the U.S. and EU member states, could be at risk.

“This could tilt the balance within the EU, and the Germans might be forced to make concessions,” he said.

In Russia, there was no sign of easing of pressure on Navalny’s organization. Yevgeny Prigozhin, a powerful businessman known as “Putin’s chef,” vowed to strip the activist and his allies “naked” as he seeks to enforce an 88 million-ruble ($1.1 million) court ruling against them that he won in a libel case.

Zero Faith

Trust between Merkel and Putin is at an all-time low and the relationship has continued to sour since Putin’s seizure of the Crimean peninsula from Ukraine in 2014 and his support for Ukrainian separatists in the eastern Donbas region.

In May, Merkel called Russia’s alleged involvement in a 2015 cyberattack on the Bundestag’s computer network “outrageous.” Meanwhile, German prosecutors have issued criminal charges for the murder of a Georgian man in broad daylight in the Tiergarten park last August. Russian state actors are behind it, they say.

That gangland-style execution was the focus of Merkel’s last meeting with Putin, at a December summit about Ukraine in Paris. At the time Merkel repeated her demand for Russian legal assistance, and Putin agreed.

But as German officials point out, no such help has been forthcoming nor is now expected.

(Updates with quotes from Kremlin spokesman starting in 8th paragraph.)

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