Five men have been taken to hospital after a crash on the A92 near Freuchie in Fife.
A grey Mercedes GLB 220 AMG collided with a black Audi at around 8.50pm on Thursday.
Six people were involved in the incident, including a 13-year-old female passenger travelling in the Mercedes who was uninjured.
A 22-year-old man, who was driving the Audi, was taken to Ninewells Hospital in Dundee with serious injuries, according to police.
Men taken to hospitals in Dundee and Kirkcaldy
The male driver of the Mercedes – aged 43 – was also taken to Ninewells.
Three men, aged 20, 19 and 21, who were all passengers in the Audi, were taken to Victoria Hospital in Kirkcaldy for treatment.
A Scottish Fire and Rescue Service spokeswoman said three appliances were sent to the scene at 9.10pm after the ambulance service asked for support.
The carriageway was closed in each direction at the Bridgend junction for about six hours as a probe into the collision was carried out by police officers.
A picture from the area taken by a local resident showed a large number of emergency vehicles at the scene.
Police appeal for information after A92 crash
PC Kevin Deehan, of Glenrothes road policing unit, said: “This has been a serious crash and our inquiries are ongoing to establish the full circumstances surrounding the incident.
“I would ask anyone who was driving in the area at the time and may have seen either car prior to the crash or anyone with dashcam footage that may assist with our investigation to get in touch with officers.
“Anyone with information can contact police via 101, quoting incident number 3172 of 2 September.”
Road reopens in early hours
Traffic Scotland confirmed that the road, which runs between Glenrothes and the Tay Road Bridge, had reopened by 4.40am on Friday.
The incident also caused problems for Stagecoach buses travelling through Fife on Thursday evening, with delays reported by local motorists.
The Scottish Ambulance Service has been approached for comment.