I found this really bad ass looking flintlock tomahawk pistol and the caption says its from the late 18th century.
This flintlock key pistol is said to be from the early 19th century. Such weapons were usually carried by jail and prison guards.
I was trying to research the real history behind this pistols but I could only find a bunch of sites bidding for their prices, so I'm not sure if a person from today's world with a really creative mind created their own pistols or if these tomahawk and key flintlock pistols in the images linked were real weapons that would have actually existed in their respective time periods.
The image of the tomahawk pistol shows something very much in the style( and of the quality) of flintlock tourist souvenirs made in the middle east, often Turkey, in the 19th c. and later. It can be a bit confusing, because they kept many of the features of a flintlock pistol of the earlier 18th c., such as a round-faced lock, and the butt being at a wide angle to the barrel. The very crude wire inlay is a common feature of these- the wire ( actually a strip) is much thicker and sloppier than on originals, and the workmanship is generally sloppy. There may have been such a thing in the 18th. c. , somewhere, but this particular one looks pretty dubious.
The key pistol link pulls up a lot of images and examples, some obviously Spanish, others not, many showing some pretty good workmanship. If someone had claimed some of them to be earlier than the 19th c., I would have believed them, they have the careful filing and decoration of what you'd expect of a very good French 18th. c. locksmithThe one indicated as early 19th. c. could very well be circa 1800: the cock and pan don't look out of place for that time. Most all of them look as though they would work: those are real locks on them, and though they may have been fired rarely, they were clearly intended to be usable.