Green’s Dictionary of Slang

cough n.

[cough v.]

1. a payment, the handing over of money.

[US]T.J. Hains Mr Trunnell Mate of the Ship ‘Pirate’ Ch. i: They wanted me to cough up stuff for the whole crowd. But nary a cough. One or two drinks is about all I can stand.

2. a confession (esp. one that is presumed to be sincere and factual); also attrib.

[UK]J. McClure Spike Island (1981) 98: He’s going to say he was tricked into this cough statement.
[UK]H.R.F. Keating Soft Detective 204: Putting the fear of God in them’s the way to get a cough.

In compounds

cough syrup (n.)

1. (US Und.) bribe money.

[US] (ref. to c.1925) Wentworth & Flexner DAS 125/1: cough syrup Bribe money paid to keep another from informing or coughing up information.

2. see cough medicine

SE in slang uses

In compounds

cough drop (n.)

1. poison, or anything disagreeable [the slogan of a popular cough lozenge, ‘cough no more’].

[UK]Marvel XV:373 Jan. 13: Give the beauties leaden cough-drops!
[UK]J. Ware Passing Eng. of the Victorian Era.

2. a disagreeable person; the image is of an informer [cough v. (1)].

[UK]Referee 27 July in Ware (1909) 94/2: ‘Honest John Burns,’ who has been returned for Battersea by the skin of his teeth, and who would have benefited considerably had his constituents given him a holiday, objects to being called ‘a cough drop’.
[UK]W.W. Jacobs ‘Artful Cards’ in Monkey’s Paw (1962) 314: Fair old cough-drop, ain’t he?

3. a ‘character’, a ‘card’.

[UK]T.W.H. Crosland ‘The Bold Militiaman’ in Absent-Minded Mule and Verses 14: Fine fellows for parade, / Done up in tasty tunics / An’ sashes an’ gold braid, / An’ loved by all the slaveys, / An’ cough-drops at their trade.
[UK]W.L. George Making of an Englishman III 317: ‘You are a cough-drop,’ she said. ‘Why, you must be barmy chucking up a good job like that.’.
[UK]J.B. Priestley Good Companions 269: Yond’s a coughdrop.
[UK]J. Curtis They Drive by Night 166: You are a funny boy. Regular cough drop, that’s what I call you.
[UK]J. Franklyn Cockney 286: ‘A lad’ in cockney slang means simply a witty, impertinent, or daring, person of either sex. [...] It is synonymous with a one, a card, a caution, a cough-drop, and very largely with an ’erb.

4. (Aus./S.Afr.) a pretty woman.

[Aus]Dead Bird (Sydney) 27 Sept. 5/3: If you should want a tart, Ask a Special. / He knows their names by heart, / Does a Special. / He can fit you in a trice / With a cough-drop plump and nice.
[UK]Partridge DSUE (8th edn) 258/1: S. Africa 1942+.
cough medicine (n.) (also cough syrup)

(US) whisky.

Marshall Co. Republican (Plymouth, IN) 21 Feb. 3/1: We observe that whisky labeled ‘cough medicine’ is the favorite beverage of some heavy literary men.
[US]Salt Lake Trib. (UT) 13 Feb. 3/6: ‘Give me twelve bottles of cough medicine.’ [...] He inquired if there was sickness in the family. ‘Why, no,’ replied the purchaser. ‘Are you not wise? This is only booze’.
Small Story of 47tb 128: Everybody invests in a little ‘cough medicine.’ [Ibid.] 128: No more ‘cough syrup.’ [HDAS].
Public ledger (Maysville, KY) 30 Nov. 4/1: Prohibition agents [...] confiscated $600 worth of gin and ‘cough medicine’.

In phrases

soften one’s cough (v.)

(Irish und.) to render someone susceptible to confessing.

[Ire]Breen & Conlon Hitmen 119: A year in custody had not softened Wilson’s cough.