diff --git a/lib/marked.js b/lib/marked.js
index 2d2baca1..c8236e95 100644
--- a/lib/marked.js
+++ b/lib/marked.js
@@ -475,7 +475,7 @@ var inline = {
 };
 
 inline._scheme = /[a-zA-Z][a-zA-Z0-9+.-]{1,31}/;
-inline._email = /[a-zA-Z0-9.!#$%&'*+/=?^_`{|}~-]+(@)[a-zA-Z0-9](?:[a-zA-Z0-9-]{0,61}[a-zA-Z0-9])?(?:\.[a-zA-Z0-9](?:[a-zA-Z0-9-]{0,61}[a-zA-Z0-9])?)+(?![-_])/
+inline._email = /[a-zA-Z0-9.!#$%&'*+/=?^_`{|}~-]+(@)[a-zA-Z0-9](?:[a-zA-Z0-9-]{0,61}[a-zA-Z0-9])?(?:\.[a-zA-Z0-9](?:[a-zA-Z0-9-]{0,61}[a-zA-Z0-9])?)+(?![-_])/;
 
 inline.autolink = replace(inline.autolink)
   ('scheme', inline._scheme)
@@ -518,6 +518,7 @@ inline.gfm = merge({}, inline.normal, {
   url: replace(/^((?:ftp|https?):\/\/|www\.)(?:[a-zA-Z0-9\-]+\.?)+[^\s<]*|^email/)
     ('email', inline._email)
     (),
+  _backpedal: /(?:[^?!.,:;*_~()&]+|\([^)]*\)|&(?![a-zA-Z0-9]+;$)|[?!.,:;*_~)]+(?!$))+/,
   del: /^~~(?=\S)([\s\S]*?\S)~~/,
   text: replace(inline.text)
     (']|', '~]|')
@@ -611,6 +612,7 @@ InlineLexer.prototype.output = function(src) {
 
     // url (gfm)
     if (!this.inLink && (cap = this.rules.url.exec(src))) {
+      cap[0] = this.rules._backpedal.exec(cap[0])[0];
       src = src.substring(cap[0].length);
       if (cap[2] === '@') {
         text = escape(cap[0]);