3.31 oz mixed with ice, 0.91 oz of it pure alcohol
Melt
Shaken: +20 % of the pre-batch, +0.66 oz of water
Served
3.31 + 0.66 = 3.97 oz in the glass
Strength
0.91 ÷ 3.97 = 22.9 % ABV as served
Ethanol
0.91 oz × 29.57 ml × 0.789 g/ml = 21 g · about 149 kcal from the alcohol alone
IN THE GLASS
VANILLIN
FROM BOURBON · from oak barrel aging
Formula
C₈H₈O₃
Mass
152.15 g/mol
IUPAC
4-hydroxy-3-methoxybenzaldehyde
Bourbon's fingerprint, extracted from the charred American oak the law requires for aging. Same molecule as the vanilla bean's signature, so a well-aged bourbon legitimately tastes like vanilla. Chemistry, not metaphor. Cognac, aged rum, tequila reposado all extract vanillin from oak too. Different barrels, same molecule.
The clove note, a phenylpropanoid that shows up wherever a recipe calls for clove, allspice, or nutmeg, and in rye whiskey through oak-barrel extraction. Anesthetic at high concentration; dentists used clove oil for centuries before lidocaine. The numbing sensation on the tongue from biting a whole clove is eugenol blocking nociceptor signaling at the contact point.
Lemon's defining note: technically a mix of two geometric isomers (geranial and neral) that read as the same aroma to the nose. Lemon peel, lemongrass, lemon verbena, and Indian chai all carry it. In cocktails it's what a lemon twist contributes that lemon juice can't: the volatile expressed from the oil glands, not the acid from the pulp.
Bourbon, allspice dram, lime, sugar and Angostura. Allspice dram (pimento liqueur) brings eugenol, methyl eugenol and 1,8-cineole, clove-and-peppercorn aromatics built into a sour. ABV is about 25%. A sour-category drink with a winter-spice profile.
PROVENANCE
First published in W.J. Tarling's 1937 Café Royal Cocktail Book. The name's origin is uncertain: possibly from 'twisting the lion's tail', old American slang for provoking Britain. Allspice dram (Wray & Nephew's Pimento Liqueur or St. Elizabeth Allspice Dram in modern form) is what makes the drink work; it's a single-ingredient warmth that bridges bourbon and lime. The drink fell out of repertoire for some seventy years; Paul Clarke unearthed it in 2005, and Ted Haigh's 2009 edition of Vintage Spirits and Forgotten Cocktails restored it.