Etymology
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compensate (v.)

1640s, "to be equivalent;" 1650s, "to counterbalance, make up for, give a substitute of equal value to," from Latin compensatus, past participle of compensare "to weigh one thing (against another)," thus, "to counterbalance," etymologically "to weigh together," from com "with, together" (see com-) + pensare, frequentative of pendere "to hang, cause to hang; weigh; pay" (from PIE root *(s)pen- "to draw, stretch, spin"). Meaning "to recompense, remunerate" is from 1814. The earlier verb in English was compense (late 14c.). Related: Compensated; compensating.

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uncompensated (adj.)
1774, "not compensated by any good," from un- (1) "not" + past participle of compensate (v.). Meaning "not recompensed" is attested from 1830.
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overcompensate (v.)

also over-compensate, "compensate excessively," 1758 (implied in over-compensated), from over- + compensate. Related: Over-compensating.

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compensatory (adj.)

"serving to compensate," c. 1600, probably from or modeled on French compensatoire, from Latin compensatus, past participle of compensare (see compensate). Psychological sense is from 1921.

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compensable (adj.)

"capable of being compensated," 1660s, from French compensable (16c.), from compenser, from Latin compensare (see compensate). Middle English had the simple verb compense "make up for (something), counterbalance, compensate; requite; satisfy (a need)," from Latin compensus, but compensate seems to have replaced it. The Old French adjective compensable meant "to consider, ponder."

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indemnify (v.)
"compensate for loss or expense," 1610s, from Latin indemnis "unhurt" (see indemnity) + -fy. Related: Indemnified; indemnifying. "Indemnify formerly meant to save a person from damage or loss, but now much more often means to make good after loss or the damage of property." [Century Dictionary]
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fine (n.)
c. 1200, "termination, end; end of life," from Old French fin "end, limit, boundary; death; fee, payment, finance, money" (10c.), from Latin finis "end" (see finish (v.)), in Medieval Latin also "payment in settlement, fine or tax."

Modern meaning "exaction of money payment for an offense or dereliction" is via sense of "sum of money paid for exemption from punishment or to compensate for injury" (mid-14c., from the same sense in Anglo-French, late 13c.) and from phrases such as to make fine "make one's peace, settle a matter" (c. 1300). Meaning "sum of money imposed as penalty for some offense" is first recorded 1520s.
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penal (adj.)

"of or pertaining to punishment by law," mid-15c., from Old French peinal (12c., Modern French pénal) and directly from Medieval Latin penalis, from Latin poenalis "pertaining to punishment," from poena "punishment," from Greek poinē "blood-money, fine, penalty, punishment," from PIE *kwoina, from root *kwei- "to pay, atone, compensate" (source also of Greek timē "price, worth, honor, esteem, respect," tinein "to pay a price, punish, take vengeance;" Sanskrit cinoti "observes, notes;" Avestan kaena "punishment, vengeance;" Old Church Slavonic cena "honor, price;" Lithuanian kaina "value, price").

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recompense (v.)

c. 1400, recompensen, "to redress, provide as an equivalent," from Old French recompenser (14c.) and directly from Medieval Latin recompensare "to reward, remunerate," from Latin re- "again" (see re-) + compensare "balance out," etymologically "weigh together," from com "with, together" (see com-) + pensare, frequentative of pendere "to hang, cause to hang; weigh; pay" (from PIE root *(s)pen- "to draw, stretch, spin"). For the financial sense of the Latin verb, see pound (n.1).

By early 15c. specifically as "to compensate, pay for services rendered or for loss of property, rights, etc.; make amends for by some equivalent; dispense punishments or rewards." "The spelling -ence is more frequent than the etymological -ense ... until the 19th c." [OED]. Related: Recompensed; recompensing.

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pain (n.)

late 13c., peine, "the agony suffered by Christ;" c. 1300, "punishment," especially for a crime, "legal punishment of any sort" (including fines and monetary penalties); also "condition one feels when hurt, opposite of pleasure," including mental or emotional suffering, grief, distress; from Old French peine "difficulty, woe, suffering, punishment, Hell's torments" (11c.), from Latin poena "punishment, penalty, retribution, indemnification" (in Late Latin also "torment, hardship, suffering"), from Greek poinē "retribution, penalty, quit-money for spilled blood," from PIE *kwei- "to pay, atone, compensate" (see penal).

The early "punishment" sense in English survives in phrase on pain of death. Also c. 1300 the word was used for the torments of eternal damnation after death. The sense of "exertion, effort" is from late 14c.; pains "great care taken (for some purpose), exertion or trouble taken in doing something" is recorded from 1520s.

 Phrase give (someone) a pain "be annoying and irritating" is by 1895; as a noun, localized as pain in the neck (1924) and pain in the ass (1934), though this last might have gone long unrecorded and be the original sense and the others euphemisms. First record of pain-killer "drug or herb that reduces pain" is by 1845.

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