GABA -> GBL w/ KMnO4?

[hester18]

Is there a write up on oxidizing GABA using KMnO4 instead of the highly toxic Sodium Nitrite? or is there any conjecture about the process I might be inquiring about?

[Vitus_Verdegast]

Primary aliphatic amines yield, as seen with anilines, diazonium salts on treatment with HNO₂. Aromatic diazonium salts are stable, but that is not the case with aliphatic diazonium salts, which break down fast to yield a mixture of alcohols and alkenes.

RNH₂ + HNO₂ ^__> [RN₂⁺](unstable) ^__H₂O^__> N₂ + ROH

In most cases a complex mixture of alcohols and alkenes are obtained.

I doubt that KMnO₄ oxidation of GABA would yield anything useful, unless you have a reference to prove me wrong.

BTW NaNO₂ is not *highly* toxic, not like NaN₃ or cyanides or alikes. It is toxic yes, but you should always wear protection anyway, and no-one is telling you to eat it.

[methyl_ethyl]

In addition to that, Sodium nitrite has been used in the curing of meats for ages.  Sodium nitrite solutions are actually injected into meats such as hams, and rubbed onto porkbellies (for bacon).  There were some hypotheses in the seventies that N-Nitrosamines may be produced in the stomach due to consumption of sodium nitrite, however these hypotheses have been proven incorrect in recent studies.

Further reading on the safety of Sodium Nitrite:

http://www.medem.com/MedLB/article_detaillb.cfm?article_ID=ZZZ80XEN0IC&sub_cat=380

EDIT: I hope people do not get the wrong idea from the above post, I just wanted to present that sodium nitrite is used in the food industry (in small amounts).   If you were to eat 10g of Sodium Nitrite crystals you could experience, methemoglobinemia, cyanosis, respiratory arrest and other adverse health conditions.  I am not saying this stuff is non-toxic in any way, the NFPA health rating is 2 out of a possible four.

sorry for any confusion,

methyl_ethyl