Sustained capital outflows and overwhelmingly bullish dollar against major currencies predominantly weighed on the local forex sentiment.
The rupee came under pressure following a sudden reversal in dollar movement overseas on rising Treasury yields along with speculations that President Donald Trump might favour a monetary "hawk" as successor to Federal Reserve Chair Janet Yellen.
The home currency had reclaimed a three-week high overnight buoyed by strong macroeconomic data and also supported by record-breaking local equities.
In the meantime, the domestic equity markets endured some rough weather after scaling historic peaks as traders adopted a defensive stance, triggering profit-taking at higher levels.
Most Asian stocks managed another session of gains amid milestone US stock indices closing.
The flagship Sensex ended with a modest loss of 24.48 points at 32,609.16 after climbing a new peak of 10,251.85 in early trade.
In contrast, the broader Nifty finished at a record high of 10,234.45 with a gain of 3.60 points after briefly touching the 10,251.85 milestone for the first time, stretching its powerful record-setting bull-run for the third session.
It later picked up bearish momentum owing to extreme dollar pressure and once again breached the key support level of 65 to hit an intra-day low of 65.0350 in afternoon deals.
Finally, the local unit settled at 65.02, revealing a steep loss of 28 paise, or 0.43 per cent.
The RBI, meanwhile, fixed the reference rate for the dollar at 64.9226 and for the euro at 76.4204.
The dollar index, which measures the greenback's value against a basket of six major currencies, was trading firmly higher at 93.42 in early trade.
The local currency, however, held steady against the Japanese yen at 57.94 per 100 yens.
In forward market today, premium for dollar drifted sharply due to good receiving from exporters.
The benchmark six-month premium payable in March declined to 117-119 paise from 121-123 paise and the far forward September 2018 contract dropped to 256-258 paise from 260-262 paise yesterday.
On the international energy front, crude prices staged a steep jump as risk premium returned to oil markets on the back of rising tensions between the US and Iran and on news of Iraqi forces entering Kurdistan amid raising concerns over supply woes.
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