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In general, the (parametric) h-principle for Legendrian immersions implies that Legendrian immersions f:L->(M,\xi) are classified up to homotopy (through Legendrian immersions) by the following bundle-theoretic invariant: Choosing a compatible almost complex structure on \xi allows one to complexify the differential of f to an isomorphism d_C f: TL\otimes C -> f*\xi, and the relevant invariant is the homotopy class of this isomorphism of complex vector bundles (of course this is independent of the almost complex structure since the space of compatible almost complex structures is contractible).

The above holds in any contact manifold (M,\xi) of arbitrary dimension. Of course when M is 3-dimensional and L is S^1, f^*\xi is the unique complex vector line bundle over S^1, automorphisms of which are parametrized up to homotopy by pi_1(U(1))=Z. So (given that the h-principle also implies that any loop in a 3-manifold is homotopic to a Legendrian loop) it appears to always be the case that the "Legendrian fundamental group" surjects onto the standard fundamental group, with kernel Z.

When M=R^3 this invariant is equivalent to the rotation number that Steven mentioned. There's a proof of the relevant h-principle in the book by Eliashberg and Mishachev. The above discussion is partly based on Section 3.3 of arXiv:0210124 by Ekholm-Etnyre-Sullivan.

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In general, the (parametric) h-principle for Legendrian immersions implies that Legendrian immersions f:L->(M,\xi) are classified up to homotopy (through Legendrian immersions) by the following bundle-theoretic invariant: Choosing a compatible almost complex structure on \xi allows one to complexify the differential of f to an isomorphism d_C f: TL\otimes C -> f*\xi, and the relevant invariant is the homotopy class of this isomorphism of complex vector bundles (of course this is independent of the almost complex structure since the space of compatible almost complex structures is contractible).

The above holds in any contact manifold (M,\xi) of arbitrary dimension. Of course when M is 3-dimensional and L is S^1, f^*\xi is the unique complex vector bundle over S^1, automorphisms of which are parametrized up to homotopy by pi_1(U(1))=Z. So (given that the h-principle also implies that any loop in a 3-manifold is homotopic to a Legendrian loop) it appears to always be the case that the "Legendrian fundamental group" surjects onto the standard fundamental group, with kernel Z.

When M=R^3 this invariant is equivalent to the rotation number that Steven mentioned. There's a proof of the relevant h-principle in the book by Eliashberg and Mishachev. The above discussion is partly based on Section 3.3 of arXiv:0210124 by Ekholm-Etnyre-Sullivan.