$re = '/\s*(?:.*?[:=;]|ORCPT|for|domain of|ESMTPSA id)?\s*(?:"?([\w ]*?)[ "<])?\s*<?([\w.]*?@[\w.]*)>?/i';
$str = 'John Smith <john.smith@gmail.com>
John Smith <johnsmith@gmail.com>
"John Smith" <johnsmith@gmail.com>
"John" <johnsmith@gmail.com>
John Smith<johnsmith@gmail.com>
<johnsmith@gmail.com>
johnsmith@gmail.com
mailto:johnsmith@gmail.com
"John"<johnsmith@gmail.com>
To: John Smith <john.smith@gmail.com>
From: John Smith <john.smith@gmail.com>
Reply-to: john.smith@gmail.com
Return-path: <john.smith@gmail.com>
Message-id: <john.smith@gmail.com>
References: <john.smith@gmail.com>
Original-recipient: rfc822;john.smith@gmail.com
for john.smith@gmail.com
ESMTPSA id <john.smith@gmail.com>
domain of john.smith@gmail.com
envelope-from=john.smith@gmail.com
(ORCPT john.smith@gmail.com)';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
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 PHP, please visit: http://php.net/manual/en/ref.pcre.php