If a person transgressed and used Ma'aser Sheni as collateral or as a guarantee (for a new loan), it should follow this Baraisa...

(Rabban Shimon ben Gamliel): One who eats his Ma'aser Sheni (outside Yerushalayim), whether inadvertently or intentionally, he should cry out to Heaven for forgiveness (as there is nothing else he can do).

(Rebbi): If it was done inadvertently, he should cry out to Heaven; if intentional, he must separate money to their value and treat it as Ma'aser Sheni.

(Rabban Shimon ben Gamliel): And if he had used Ma'aser Sheni money - if done inadvertently, he should cry out to Heaven; if done intentionally, he should separate money to their value and treat it as Ma'aser Sheni.

(Rebbi): Whether inadvertently or intentionally, he should separate money to their value and treat it as Ma'aser Sheni.

(R. Zerikah citing Chikiyah): The Halacha follows Rebbi for money and Rabban Shimon ben Gamliel for produce.

(R. Yaila): Such a case once occurred and they ruled like Rebbi for money.

Or the law (of a person who transgressed and used Ma'aser Sheni as a guarantee or collateral) should follow the Mishnah (in Maseches Sheviis 2:6) that taught - One may not plant, sink or graft on the eve of Sheviis less than 30 days before Rosh Hashana. If one did plant, graft or sink then, he must uproot them.

Question: If he did not uproot them, what is the law of their fruits?

R. Ba and R. Ila were sitting in Tzur. Such a case came before them and R. Ila ruled that the fruits must be spilled out (as they are prohibited to eat).

(R. Ba): I wasn't with them in the attic when they ruled to prohibit the fruits.

They went outside and heard R. Yona and R. Yitzchak bar Tavlai citing R. Elazar that one may not apply something new to the decree (that it must be uprooted and also say that the fruits are prohibited).

(R. Yosi): R. Yitzchak bar Tivlai citing R. Elazar said that one may not add to the decree. (This means the same as the previous statement, but it was just expressed in a different way). (Nevertheless, the Gemara proves from here that if a person did use Ma'aser Sheni as a guarantee or collateral, he is not penalized.)

(R. Yaakov bar Acha citing R. Zeira): From that which the Mishnah only taught - One may not use it for collateral, but it didn't teach that one may not use it as a guarantee - this shows that if one transgressed and used it as a collateral, we penalize him; but if he used it as a guarantee (for a new loan), we do not penalize him.

(The Mishnah taught that one may not use Ma'aser Sheni as a weight.) One may not weigh it against money, even if he wishes to weigh out a Sela of Chulin in order to make it a Sela of Ma'aser Sheni.

Question: If he had a Sela of Ma'aser Sheni that is of known exact weight, may he weigh out against it another Sela of Ma'aser Sheni in order for its exact weight to be known to him? Similarly, if two brothers divide their father's estate, may they weigh Ma'aser Sheni coins against each other to do so? (The Gemara leaves these questions unanswered.)

The Mishnah taught - 'In Yerushalayim, one should not say to his friend, "Take this wine and give me oil''.' Nor should he say, "Take this oil and give me wine''. But he may say, "Take this wine as you don't have wine'' or "Take this oil as you don't have oil''. If he said, "Take this wine as I don't have oil'', it was suggested that it should be prohibited. (as it is like an exchange). However, a Baraisa was found that teaches that it is permitted.

Question: Why isn't it prohibited as an exchange of Ma'aser Sheni?

Answer: Since they didn't discuss a price, it's not an exchange - as he wouldn't be able to extract it from him legally.

Question: If it's not an exchange, why did he say, "Take for yourself wine as I don't have oil''?

Answer: He intended to say, "If I would have oil, I would give you that as well''.

The Mishnah taught that a person may give his friend a free gift of Ma'aser Sheni.

The Mishnah follows the view of R. Meir, who said that a gift is unlike a sale.

(R. Yosi): (Disagreeing) It follows all opinions and it's like the Baraisa that taught - If a person said to his friend, "What did you eat today?'' and the friend replied, "Summer fruits'', he would understand that the person had eaten the meat of a Bechor (firstborn). (What's the connection?) Just as summer fruits are sold for cheap (as they are in great abundance) so too Bechor meat is sold for cheap.

If the person answered that he had eaten 'Mun', the questioner understand that he meant Ma'aser Sheni. Just as the Mun (i.e. Manna) was given as a gift (in the desert) so too Ma'aser Sheni may be given as a gift. (This Baraisa therefore shows that one may give Ma'aser Sheni as a free gift).

Another question against R. Meir: All agree that one may not sell Maaser Behemah, but it may be given as a gift; so too Ma'aser Sheni, even though it may not be sold, it may be given as a gift.

R. Mana didn't say this - rather, he said that the statement in the Mishnah that allows giving a gift of Ma'aser Sheni, is like R. Yehuda (rather than Rabbanan) who said that Ma'aser Sheni is considered one's own property.

Question: All agree that Maaser Behemah is not like one's own property, but it may be given as a gift; so too all must agree that Ma'aser Sheni may be given as a gift!