Police in Germany have fired water cannon and pepper spray at anti-coronavirus restriction protesters.
Officers in Berlin said the thousands of demonstrators refused to heed their requests to wear face masks and social distance in line with regulations.
They fired the cannon into the crowd outside the Brandenburg Gate on Wednesday as riot police swept through and carried away some protesters.
Fireworks and flares were thrown in response from the protesters who ranged from the far-left to the far-right and included families and students.
Police detained 190 people while nine officers were injured.
The protests happened as German MPs debated a bill that will give the government the legal backing to issue social distancing rules, close shops and other venues, prevent drinking in public and require masks to be worn in public to slow the spread of COVID-19.
Most people in Germany are in support of the measures but a vocal minority has staged frequent rallies around the country arguing that the restrictions are unconstitutional.
The lower and upper houses of parliament passed the measures which are expected to be signed into law by German president Frank-Walter Steinmeier later on Wednesday.
Several protests due to take place outside the parliament building had already been banned due to security concerns.
Fencing has been put up around the area, including the Bundestag, the federal chancellery and presidential residence and offices.
But protesters gathered early outside the metal cordons by the Brandenburg Gate and on bridges and streets.
One sign carried by a protester read “we want our lives back”, while another said “put banks under surveillance, not citizens”.
A demonstrator held a placard showing leading German virologist Christian Drosten in prison clothes with the word “guilty”.
Another held a flag with a picture of Donald Trump and an image linked to the right-wing conspiracy theories QAnon.
The measures have been likened by some to the 1933 Enabling Act which allowed the Nazis to enact laws without parliamentary approval.
Reacting to the accusation, German foreign minister Heiko Maas said on Twitter: “Everyone, naturally, has the right to criticise the measures, our democracy thrives through the exchange of different opinions.
“But whoever relativises or trivialises the Holocaust has learned nothing from our history.”
Germany was praised for its handling of the first wave of the virus but has recently seen a steep increase in new cases and is now halfway through a second partial lockdown.
The country has had 833,000 COVID-19 cases and more than 13,000 deaths.