Fractalhead Posted May 29, 2002 After finding out that isosafrole is present in Ylang Ylang (Cananga odorata) essential oil the other day, I began to examine the structure and try to figure out whether or not the enzymes that probably metabolise myristicin and safrole into active aminated forms would also convert isosafrole to a similarly aminated form. The only problem i could see was the fact that the pi-bond on the 3 membered chain was in the middle of the group rather than right at the end as is the case with myristicin and safrole. Just off the top of my head, I'm wondering if the metabolic product (if there is one) might not be primary amine. Actually, it seems more likely to be a primary amine than anything else. Hmmm anyway... I haven't yet put in serious investigation... i just wanted to put it out to anyone who has an idea of what might happen to isosafrole in the body. Especially since Ylang Ylang oil smells so good, is a good aphrodisiac (in my opinion), and is readily available in well prepared form at the chemist. mmmmmm ylang ylang.... [This message has been edited by Fractalhead (edited 30 May 2002).] Share this post Link to post Share on other sites
Adrian Posted May 30, 2002 Get OUT! Seriously? Isosafrole? Correct me if I'm wrong (I don't have my data here with me) isn't this much sort after by 'cooks' wanting to produce MDA & friends? Is there any data on %? I'll have a look tomorrow. Another obscure and misguided question here… Would it be safe to assume that a massage oil containing say; a nicely blended mix of sassafras, nutmeg & Ylang Ylang essential oils could pose a dual purpose, and be legal to possess and use as a "highly erotic essential oil", maybe even a dash of calamus oil for good measure? Dangerous; most likely, fun; probably. And one more…information about ingestion of sassafras oil/ safrole seems weak at best. I’m sure anything repeatedly pumped with any substance over long periods is going to exhibit signs of poor health. Can someone confirm this please? (a sarcastic interpretation of some of the scientific papers about such) I’m just wondering if 50% of the rats that were repeatedly injected with 150mg/ kg of safrole over 30-60months, were not overly happy about having a potential increased risk of cancer, but when asked enjoyed the short term effects and stated that they’d be quite happy to settle (out of court) for a new water bottle and a nice stick of celery. (YawWnNn) Share this post Link to post Share on other sites
Fractalhead Posted May 30, 2002 The book, i think, was called Phytochemical Products or something like that... I'll post it later when i get a proper reference to the cananga thing. I couldn't find any link between cananga and isosafrole in the great Encyclopaedia of Natural Products, but that doesn't mean its not in there. I will strive to find out the % content reported. I just read that apparently, in a dog, safrole and isosafrole are 'both' metabolised, somewhere along the line, to 3,4-methylenedioxybenzoic acid and then this forms an ester glucuronide and a glycine conjugate. Apparently this glycine conjugate has been isolated from human urine. I've also found some leads to myristicin and safrole metabolism which will have to wait till i finish an assignment. i can't afford to go and rub a whole $20 bottle of ylang ylang essential oil all over myself anyway... [This message has been edited by Fractalhead (edited 30 May 2002).] Share this post Link to post Share on other sites
Fractalhead Posted June 1, 2002 Ok, the book that says isosafrole is found in Cananga odorata is: Harborne, J.B. 1999. Phytochemical Dictionary - A Handbook of Bioactive Compounds from Plants - 2nd Edition, Taylor Francis It says that isosafrole is 'moderately toxic' to humans like safrole and that it is a cytochrome p450 enzyme inductor - presumably the enzymes partly or wholey responsible for the biotransformation of safrole into active metabolites. More info soon Share this post Link to post Share on other sites
theobromos Posted June 1, 2002 Cytochrome P450 is responsible (amongst many other activities) for producing the nasty 1´-hydroxy compounds compounds. The "good" enzymes are probably the transaminases found in active muscles. A search for isosafrole in essential oils led to Duke´s databases (crap but when nothing else is around...). Three plants (Micromeria juliana leaf 0-290 ppm, Cananga odorata flower and Angelica sinensis root(Dong Quai)) have isosafrole, according the query but contains no chemicals according to the database. The reference at the query gives Kirimer, N., Ozek, T., and Baser, K.H.C. 1991. Composition of the Essential Oil of Micromeria congesta. J. Ess. Oil Res., 3: 387-393. But the entry for M. congesta has no isosafrole listed. Micromeria are little mint relatives that are easily grown. 1% total essential oil so separation of 0.029% could be tricky. Nutmeg and star anise contain some isosafrole, which shows how crap Duke is. He might be forgiven for not knowing Boronia safrolifera if he updated his databases once a century. Isosafrole is probably a lot safer for the liver than safrole according to www.oehha.ca.gov/prop65/pdf/estragf.pdf If I remember correctly isosafrole has the double bond at the free end of the sidechain so is less likely to be hydroxylated at the 1´-position. Share this post Link to post Share on other sites
theobromos Posted June 1, 2002 And JB Harborne really pisses me off too. He sometimes make assumptions and has a smaller database than I do. Share this post Link to post Share on other sites
Fractalhead Posted June 2, 2002 Yeah, i thought it was a bit dodgey that Harborne didn't give any reference to support the cananga thing or many other things at all... Share this post Link to post Share on other sites
thatpersonthatiam Posted June 2, 2002 safrole and isosafrole r pretty damned toxic. theyre used in the synthesis of mdma, mda, mdea, and watever other analogues there r. the safrole supplies the 'methylenedioxy' bit and if add ammonia u get mda, methylamine/nitromethane u get mdma(ecstacy), ethylamine/nitroethane and u get mdea. but of course u need to reductivly aminate it. the common method used here is aluminium amalgum Share this post Link to post Share on other sites
theobromos Posted June 7, 2002 Yeah, no bloody references, the time that man has wasted for me... thatpersonthatiam, do you have some reason to believe that isosafrole is "pretty damned toxic"? Share this post Link to post Share on other sites
