Etymology
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ointment (n.)

"unctuous medicinal salve for external application," late 13c., oynement, from Old French oignement "ointment, salve, unguent," from Vulgar Latin *unguimentum, from Latin unguentum (see unguent). The first -t- emerged early 14c. in English, from Old French, which got it by influence of oint, past participle of the verb oindre "to anoint."

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fly (v.2)

"run away," Old English fleon, flion "fly from, avoid, escape;" essentially a variant spelling of flee (q.v.). In Old English, this verb and fleogan "soar through the air with wings" (modern fly (v.1)) differed only in their present tense forms and often were confused, then as now. In some Middle English dialects they seem to have merged completely. Distinguished from one another since 14c. in the past tense: flew for fly (v.1), fled for fly (v.2).

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fly (n.)

Old English fleoge "a fly, winged insect," from Proto-Germanic *fleugon "flying insect" (source also of Old Saxon fleiga, Old Norse fluga, Middle Dutch vlieghe, Dutch vlieg, Old High German flioga, German Fliege "fly"); literally "the flying (insect)" (compare Old English fleogende "flying"), from PIE root *pleu- "to flow," which is also the source of fly (v.1).

Originally any winged insect (moths, gnats, beetles, locusts, hence butterfly, etc.) and long used by farmers and gardeners for any insect parasite. Flies figuratively for "large numbers" of anything is from 1590s. Plural flien (as in oxen, etc.) gradually normalized 13c.-15c. to -s. Fly in the ointment is from Eccles. x:1. Fly on the wall "unseen observer" first recorded 1881. No flies on _____ "no lack of activity or alertness on the part of," is attested by 1866. Meaning "fish-hook dressed to resemble an insect" is from 1580s; Fly-fishing is from 1650s. Fly-catcher "bird which eats insects on the wing" is from 1670s. The fly agaric mushroom (1788) so called because it was used as a poison for flies.

The sense of "a flight, flying" is from mid-15c. From the verb and the notion of "flapping as a wing does" comes the noun sense of "tent flap" (1810), which was extended to "strip of material sewn into a garment as a covering for buttons" or some other purpose (1844). Baseball fly ball attested by 1866. To do something on the fly is 1856, apparently from baseball.

When the catcher sees several fielders running to catch a ball, he should name the one he thinks surest to take it, when the others should not strive to catch the ball on the fly, but only, in case of its being missed, take it on the bound. ["The American Boys Book of Sports and Games," New York, 1864]
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fly (v.1)

"to soar through air; move through the air with wings," Old English fleogan "to fly, take flight, rise into the air" (class II strong verb; past tense fleag, past participle flogen), from Proto-Germanic *fleugan "to fly" (source also of Old Saxon fliogan, Old Frisian fliaga, Middle Dutch vlieghen, Dutch vliegen, Old High German fliogan, German fliegen, Old Norse flügja), from PIE *pleuk-, extended form of root *pleu- "to flow."

Meaning "go at full speed" is from c. 1300. In reference to flags, 1650s. Transitive sense "cause to move or float in air" (as a flag, kite, etc.) is from 1739; sense of "convey through the air" ("Fly Me to the Moon") is from 1864. Related: Flew; flied (baseball); flown; flying. Slang phrase fly off the handle "lose one's cool" dates from 1825.

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fly (adj.)

slang, "clever, alert, wide awake," by 1811, perhaps from fly (n.) on the notion of the insect being hard to catch. Other theories, however, trace it to fledge or flash. Slang use in 1990s might be a revival or a reinvention.

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in (adj.)

"that is within, internal," 1590s, from in (adv.). Sense of "holding power" (the in party) first recorded c. 1600; that of "exclusive" (the in-crowd, an in-joke) is from 1907 (in-group); that of "stylish, fashionable" (the in thing) is from 1960.

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in- (1)
Origin and meaning of in-

word-forming element meaning "not, opposite of, without" (also im-, il-, ir- by assimilation of -n- with following consonant, a tendency which began in later Latin), from Latin in- "not," cognate with Greek an-, Old English un-, all from PIE root *ne- "not."

In Old French and Middle English often en-, but most of these forms have not survived in Modern English, and the few that do (enemy, for instance) no longer are felt as negative. The rule of thumb in English has been to use in- with obviously Latin elements, un- with native or nativized ones.

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-in (2)

word-forming element in chemistry, usually indicating a neutral substance, antibiotic, vitamin, or hormone; a modification and specialized use of -ine (2).

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-in (1)

the adverb in attached to a verb as a word-forming element, by 1960, abstracted from sit-in, which is attested from 1941 in reference to protests and 1937 in reference to labor union actions (which probably was influenced by sit-down strike) but was popularized in reference to civil disobedience protests aimed at segregated lunch counters.

As a word-forming element it was extended first of other types of protests, then by 1965 to any sort of communal gathering (such as love-in, attested by 1967; slim-in, for dieters, 1973). In labor actions it was perhaps less useful: "a mass of workers calling in sick to absent themselves in protest" was called both a sick-out (1970) and a sick-in (1974).

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in (adv., prep.)

a Middle English merger of Old English in (prep.) "in, into, upon, on, at, among; about, during;" and Old English inne (adv.) "within, inside," from Proto-Germanic *in (source also of Old Frisian, Dutch, German, Gothic in, Old Norse i), from PIE root *en "in." The simpler form took on both senses in Middle English.

Sense distinction between in and on is from later Middle English, and nuances in use of in and at still distinguish British and American English (in school/at school). Sometimes in Middle English shortened to i.

The noun sense of "influence, access (to power or authorities)," as in have an in with, is first recorded 1929 in American English. to be in for it "certain to meet with something unpleasant" is from 1690s. To be in with "on friendly terms with" is from 1670s. Ins and outs "intricacies, complications of an action or course" is from 1660s. In-and-out (n.) "copulation" is attested from 1610s.

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