Frankly, I'd be happy if bitcoin facilitated these "criminal" transactions to a much greater degree. I'm absolutely no fan of Iran or Cuba or any of the other sanctioned countries, but I think the idea that economic sanctions do more harm than good.
If BTC (or some analogous currency) does become a standard value store on the international market, I'll be interested to see if governments continue pursuing the impossible goal of imposing economic sanctions like this or if they change tactics. My guess is they'll continue pursuing the impossible goal.
Are you saying that sovereign nations don't have the right to decide who they're willing to trade with? Because that's in essence what you're saying when you say economic sanctions should end.
They have that ability through the power vested in them by the citizens, to effectively project the force that the citizenry, as a whole, desires to project.
If the citizenry cared, they can do something about that. (They don't, for a lot of reasons. And they're wrong, but they don't.)
If the government acted for the citizenry as a whole, then they wouldn't have to ban these transactions. At best, the government imposes the majority view on the minority. I think that in general this is more dangerous than helpful. Imagine that the government, with full support of 80% of all US citizens, banned doing business with anyone of Iranian descent, not just living in Iran. That's not feasible in the current climate, but it's certainly possible. I think I'd prefer it if such laws were fundamentally unenforceable.
So if country A is at war with country B then the government of A shouldn't be allowed to prevent company C from selling items which materially benefit and provide aid and comfort to country B?
Finding out how many transactions are conducted, and their value would be easier, but it may be difficult to correlate this information with the people behind them.