Brexit is projected to cost the Scottish economy up to £11.2 billion each year, according to the Scottish Government.
Leaving the European Union will also hit tax revenues by up to £3.7 billion annually, its analysis found.
First Minister Nicola Sturgeon said the figures are further evidence of the need to protect Scotland's relationship with the EU.
The Government analysis paper suggests that by 2030, Scottish GDP is projected to be between £1.7 billion and £11.2 billion per year lower than it would have been if Brexit did not occur.
Tax revenue is projected to be between £1.7 billion and £3.7 billion lower.
The paper is the first in a series that the Government plans to publish looking at the potential impact on Scotland of the UK leaving the EU.
Ms Sturgeon said: "This paper shows, in the starkest possible terms, the potentially huge cost to Scotland of being taken out of the European Union and the single market.
"This analysis - based on a wide range of sources - demonstrates that leaving the EU, under any potential alternative arrangement, will have a profound and long-lasting impact on the public finances and the wider economic and societal well-being of both Scotland and the UK as a whole.
"That stark picture outlined today means that, whatever the model of relationship with the EU which is chosen by the UK Government in their negotiations before and after Article 50 is triggered, it will not be as economically beneficial as full EU membership.
"The only way to protect Scotland's economy - and the clear benefits which come from being part of the world's biggest single market - is to work to ensure we protect our relationship with the EU.
"My Government is absolutely committed to pursuing every possible avenue and option to do that."
The First Minister, who has warned the result of June's EU referendum makes another vote on Scottish independence ''highly likely'', has already held talks with the Prime Minister, EU institutions and individual member states.
She has also set up her own expert group to advise on protecting Scotland's relationship with Europe, and has set out five key interests she will try to protect during any negotiations.
These include ''the need to make sure Scotland's voice is heard and our wishes respected'', free movement of labour, access to the single market and a say in its rules.