I'm not sure. Those transactions will be fairly identifiable and will cause problems. I'm told that already Coinbase asks if you are sending coins to an exchange and if so asks for additional documentation. Sending coins to a non-compliant exchange will likely be a serious problem at some point, if not already.
One sends the coins to one's own address first. This is critical in every case. If one uses an exchange to send coins to a third party then in most cases the exchange has by law to ask questions about the third party. This is a very important difference that many miss. In this case it makes no difference if the coin is Bitcoin, Monero or even fiat. Withdraw 200 USD in cash form the bank. No problem. Now in the US ask the bank to send 200 US to your favourite non compliant gambling site and see what happens.
Edit: The problem with Coinbase is that their business model of sending Bitcoin payments on behalf of clients requires a much stricter level of regulatory compliance than if they just stuck to being an exchange and required clients to only withdraw from and deposit to a Bitcoin address under the client's control.