Kray, from Haggerston, East London, spent 30 years behind bars for murder and friends say he struggled with his mental health during his sentence.
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He spent less than a year in Long Lartin, but reportedly made a number of attempts to end his own life amid paranoia and depression.
Bernard O’Mahoney, an old friend of Kray’s, told Channel 5: “Visiting Reggie Kray was an experience to say the least.
“He’d be sitting there, drinking brandy, he got drunk, he popped ecstasy pills and the prison officers never said nothing.
“He suffered some sort of breakdown in there.”
Speaking as part of a documentary on Long Lartin, he added that Kray never spoke openly about his mental health but “certainly had mental illness”.
Journalist and author Geoffrey Wansell revealed the details of the infamous criminal’s suicide attempts.
He said: “Reggie was disturbed during his time at Long Lartin there could be no doubt about that.
“In fact he had a particular paranoia that he was being poisoned and his cell was bugged.”
Wansell explained that Kray tried to cut his own wrists with the lenses of his spectacles and also set fire to his bed by throwing burning loo roll onto it as he tried to end his own life.
Reggie Kray and his twin brother Ronnie rose to prominence as nightclub owners in the early 1960s.
They played host to celebrities from across the world, including Frank Sinatra, Sir Cliff Richard and Dame Barbara Windsor.
However, their clubs were just one part of the empire run by The Firm, the organised crime group they led.
They had a brief alliance with the New York Mafia in the mid-60s and were also implicated in a major political scandal.
In 1964, reports emerged that Ronnie Kray, who later came out as bisexual, had engaged in a sexual relationship with Tory peer Lord Boothby and had procured male prostitutes for him.
Homosexual activity was not decriminalised in the UK until 1969.
The original story was shut down through a combination of legal action and alleged violence, but the key claims it made were proven in a 2009 documentary.
Both brothers were imprisoned in 1969 over a brace of murders.
Ronnie had shot a member of a rival gang named George Cornell in a Whitechapel pub in 1966, while Reggie had stabbed former Firm hitman Jack ‘The Hat’ McVitie at a party in 1967.
Reggie moved between a number of prisons before being released on compassionate grounds in 2000 after being diagnosed with inoperable bladder cancer.
He died just months later at his home, aged 66.
Ronnie, meanwhile, was kept in high-security prisons until he was certified insane due to paranoid schizophrenia in 1979.
He was transferred to Broadmoor Hospital, where he remained until his death in 1995.
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