Green’s Dictionary of Slang

(a) a crown or five-shilling (25p) piece.

1853		Dickens ‘Slang’ in Household Words 24 Sept. 75/2: Crownpieces are bulls, and cart-wheels.
1867		A. Sketchley in Cassell’s Mag. 327/1: He [...] says ‘This ’ere cart wheel’s a duffer’ [OED].
[1870		Sportsman (London) ‘Notes on News’ 4 Aug. 2/1: [T]hose huge cart-wheels, those five-franc pieces].
1871		Westmoreland Gaz. 14 Oct. 2/4: Governors are improved [...] since the old days, for they tip you half a skiv now, instead of a cartwheel [...] I‘ll fork out a tizzy for you.
1898		Binstead & Wells A Pink ’Un and a Pelican 155: He has gathered in our louis d’or and our five-franc cartwheels.
1898		Belfast News-Letter 11 Apr. 6/5: ‘Cartwheel’ for a crown and ‘browns’ for halfpence are intelligible enough.
1909		J. Ware Passing Eng. of the Victorian Era.
1925		Western Mail (Perth) 28 May 21/1: [from Daily Mail, London] A 5s. piece in my young days was still called a cartwheel, but no longer a tosheroon or a bull.

(b) (Can./US, also cartwheel silver dollar) a silver dollar.

1859		Calif. Police Gazette 30 Jan. 2/3: In the first portion of the day the black horse was the favorite, [...] and any quantity of ‘cart wheels’ made their appearance.
1873		J. Miller Life Amongst the Modocs 38: I gave you a whole cart-wheel, did I not? a clean twenty dollar, and told you to keep the change [DA].
1885		Donaldsville Chief (LA) 26 Sept. 1/5: We had the pleasure of seeing him stuck for seven big cart-wheels by a street fakir.
1895		J. London ‘’Frisco Kid’s Story’ in High School Aegis X (15 Feb.) 2–3: Wot? Five big cart-wheels! I’m much obliged, mister.
1907		C. M’Govern By Bolo and Krag 41: I slips ten mex cartwheels into Mrs. Clarke’s hands.
1918		G.E. Griffin ‘Me Bunkie and I’ Ballads of the Regiment 16: He sends them each pay day six ‘cart wheels’.
1929		M. Prenner ‘Sl. Terms for Money’ in AS IV:5 357: A cartwheel is a silver dollar.
c.1930		N. Kimball Amer. Madam (1981) 175: The confidence man has a lower class that will take a widow’s last hundred cartwheels (dollars) by the paper bag trick.
1946		T. Thursday ‘Raw, Medium, and Well Done’ in Blue Ribbon Western June 🌐 He asks three of the boys to place cartwheel silver dollars on the table.
1952		L. Hughes Laughing to Keep from Crying 63: Autumn in Reno! Dog-bite my onions! Stacks of shining silver dollars on the tables [...] Must be all the cartwheels in the world in Reno.
1962		S. Longstreet Flesh Peddlers (1964) 284: Las Vegas [...] and its banging of cartwheel silver dollars.
1977		(con. 1908) J. Monaghan Schoolboy, Cowboy, Mexican Spy 14: He handed me two silver ‘cartwheels’ – the first money I had ever earned.
1986		S. King It (1987) 91: You give those cartwheels to your kids.
1991		(con. 1920s) O.D. Brooks Legs 102: That’s thirty-nine cartwheels a day. More’n a hundred clams.

(c) (Aus.) a round damper marked with a cross.

1900		Tocsin (Melbourne) 13 Sept. 6/1: The march of years and of intellect has flattened the damper into a ‘cart-wheel’, in which form even the unskilled traveller fresh from the city can very easily produce a tolerably good baking [AND].
1908		G. Seagram Bushman All 216: ‘Must ’ave something to eat, Boss [...] an’ this yer cartwheel,’ pointing to the dough, ‘will keep us goin’ a day or two.’.
1916		H.L. Roth Sketches and Reminisces from Queensland 11: While thus rainbound they made a ‘cart wheel’ (a large ‘damper’), which they cooked under great difficulties inside the tent [AND].
1948		I.L Idriess Opium Smugglers 174: He smacked it top and bottom – a bonzer damper, a dinkum ‘cartwheel’.
1963		M. Anderson A River Rules My Life 99: He would bring me in a loaf of camp-oven bread. ‘Here you are, Missus,’ he would say. ‘Here’s your cart-wheel.’.

(d) (drugs) a drug in pill form, usu. amphetamine or Benzedrine; often in pl.

1966		H.S. Thompson Hell’s Angels (1967) 222: I asked what they were and somebody beside me said: ‘Cartwheels, man. Bennies. Eat some, they’ll keep you going.’.
1976		R. Sabbag Snowblind (1978) 240: The most popular word is ups. Brain ticklers, browns, cartwheels [...] are words of the sixties and are out of use now.
2001		ONDCP Street Terms 5: Cartwheels — Amphetamine.