use strict;
my $str = 'am
pm
P.M.
10:56pm : start a new line
10:43 a.m.';
my $regex = qr/(?i)(?<!\b[01][0-9])(?<!\b[2][0-3])([^\S\r\n]*:)[^\S\r\n]*(?![0-5][0-9](?:[ap]\.?m\b\.?)?)/p;
my $subst = '\\1\\n';
my $result = $str =~ s/$regex/$subst/rg;
print "The result of the substitution is' $result\n";
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Perl, please visit: http://perldoc.perl.org/perlre.html