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Safrole (Root beer or amphetamines?)

Category: Food
Posted on: June 8, 2007 7:42 PM, by Molecule of the Day

Safrole is a simple organic compound found in sassafras oil:


InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2

It has a pleasant odor and used to be used to flavor root beer, but sassafras oil has fallen out of favor in the past few years for a few reasons: first, safrole has been deemed carcinogenic and banned as a flavoring agent by the US FDA. Second, it's actually a drug precursor - like pseudoephedrine-containing allergy medicines, it's not illegal to buy sassafras oil (as far as I know, I've never tried!), but it's watched closely by US drug enforcement. The people buying pints at a time probably aren't making a few gallons of root beer, and safrole-free sassafras oil is available for flavoring purposes anyway, so you might have some 'splaining to do if you were to pick up a case.

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Comments

1

Hmmm, that molecular structure looks more like MDMA than amphetamine proper.

Posted by: Mike Jenkins | June 8, 2007 10:41 PM

2

Yes, safrole is used to make Ecstasy, not regular amphetamines.

Posted by: Abe | June 9, 2007 3:52 AM

3

Safrole has such a lovely smell....like an entire candy store worth of sweetness.

Does anyone else think the structure of safrole looks like a cute little mouse?

Posted by: Vince Noir | June 10, 2007 4:40 PM

4

I think it looks like a frog who has had a leg pulled off.

Posted by: Jones | June 11, 2007 11:38 AM

5

Yes, I too think that the molecule looks like a cute little mouse.

Posted by: Katherine Sharpe | June 12, 2007 11:04 AM

6

If you like this, check out the nanoputians:
http://en.wikipedia.org/wiki/Nanoputian

Posted by: Oskar | June 12, 2007 5:02 PM

7

Is it realy carcinogenic or is it baned becouse it could be used as a drug? If the second is right I would love to get my hands on some!

Posted by: Jeboslav | June 12, 2007 5:07 PM

8

The 5-6 ring bit has a similar shape to purines. I bet it gets incorporated into DNA as a base (or the associated enzymes) and gets into all sorts of mischief. So I put my money on it being an actual carcinogen. Am I right but for the wrong reason? If not I am going to start making root beer. They take all the fun chemicals out of soft drinks and cold medicines. Childhood just has not been the same since they took the cocaine out of Coke and the heroin out of cough syrup.

Posted by: Saul Wall | June 12, 2007 9:25 PM

9

No, safrole itself isn't a drug of abuse. (It is antiseptic, and numbs the mouth, but that's about it). Safrole can be converted into MDA or MDMA (ecstasy), but not without some serious organic chemisty. Which, of course, is illegal and dangerous, and should not be attempted!!

Posted by: Vince Noir | June 12, 2007 9:45 PM

10

If those Nanoputians weren't from a famous scientist they would have been ridiculed to death. The daft thing is that, it's only the written paper presentation in 2D that it looks anything like a stickman.

Posted by: Elinker | June 13, 2007 7:23 PM

11

Amphetamine is an acronym built from IUPAC nomenclature. A-alpha (first); m=methyl (an extra methyl radical bonded to the first/alpha carbon from the amine nitrogen); ph=phenyl (the 6-carbon aromatic ring); et=ethyl (the two carbon chain bonded to the ring). Amphetamine is used as a generic term to describe phenylethylamines with that extra alpha methy from the amine function. A large share of chemical crossing the blood brain barrier are nitrogen amine types. Safrole is the molecule responsible for the root beer smell. Removing that 90% from Sassafras would defeat its purpose. In the game of chemistry converting safrole to MDMA is routine. Not difficult at All. I've done it 10 times.

Posted by: Dale DeWitt | December 2, 2007 3:33 PM

12

Sassafras can't be converted into MDMA without a real lab

Posted by: Cobra | April 17, 2009 8:16 AM

13

Another note: Safrole was used extensively for ridding unsavory smells from saponified animal tallow (soap making). I've not investigated current commerce but huge amounts are shipped around the world from Asian tree sources. Its North American counterpart Sassafras xxxxx ranges 2-? percent in the root bark though whole trees are consumed to those aims. Its use for mid 1900s beverages was supplanted by caramel and might find current use in legit soapmaking. Aroma Therapy makes legitimate claims for the unaltered steam distillate and clandestine entrepreneurs develop around with organized criminal backing working cat/mouse alongside stuffy DEA operations.

Posted by: Dale Thomas DeWitt | June 11, 2010 9:07 PM

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