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Topic: Isosafrole

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	516. Safrole (WHO Food Additives Series 16)
		Administration of ethionine largely inhibited the increased hydroxylation from safrole and isosafrole and methionine reversed the inhibition, indicating that safrole or isosafrole pretreatment produces new synthesis of liver microsomal hydroxylases.
		Safrole, dihydrosafrole and isosafrole were fed in the diet at levels of 0, 1000, 2500 and 10 000 ppm (0, 0.1, 0.25 and 1%) to groups of 10 male and 10 female rats and at a level of 5000 ppm (0.5%) to groups of 25 males and 25 females for two years.
		With isosafrole, growth was depressed in both sexes at 5000 and 10 000 ppm (0.5 and 1%) and in the females at the two lower doses.
	www.inchem.org /documents/jecfa/jecmono/v16je22.htm (7375 words)

	Electrochemical Oxidation of Isosafrole to Piperonal - [www.rhodium.ws]
		Electrochemical Oxidation of Isosafrole to Piperonal - [www.rhodium.ws]
		On the other hand, an electrochemical oxidation would be a promising method for a piperonal synthesis from isosafrole because an electrooxidative bond cleavage of carbon-carbon double bonds is possible in principle.
		A mixture of Isosafrole (2) (100 mg, 0.62 mmol) and NaBr (192 mg, 1.9 mmol) dissolved in MeCN (7 mL) and H
	www.erowid.org /archive/rhodium/chemistry/isosafrole.electro.html (1506 words)

	Report of error in quantity references for Isosafrole and Safrole (Site not responding. Last check: 2007-10-20)
		At base offense levels 12 and 14 in the Chemical Quantity Table in §2D1.11, the Commission inadvertently listed the quantity levels for Isosafrole and Safrole in grams (indicated by the symbol "G") rather than in kilograms (which would have been indicated by the symbol "KG").
		The error first appeared in Amendment 541 to the Guidelines Manual, effective May 1, 1997, and was repeated in the November 1, 1997 and November 1, 1998 editions.
		However, if you are aware of any affected case (particularly a case for which the Commission may not have received complete documentation), we urge you to immediately notify the Commission, the court, and the parties involved so that appropriate corrective action may be taken.
	www.ussc.gov /1998GUID/safrole.htm (275 words)

	ARCHIVE - FOOD SURVEILLANCE INFORMATION SHEETS
		A summary of the levels of pulegone, menthol, coumarin, safrole and isosafrole found in peppermint, cinnamon-containing and other herbal teas, analysed on a dry weight basis, is given in Table 2.
		A summary of the levels of pulegone, menthol, coumarin, safrole and isosafrole found in infusions of the various teas is given in Table 3.
		Neither safrole nor isosafrole was detected in any of the herbal teas analysed, while pulegone and menthol were found only in peppermint and peppermint-containing teas, with most at low levels.
	archive.food.gov.uk /maff/archive/food/infsheet/1996/no99/99bap.htm (1974 words)

	The prevention of CCl4-induced liver necrosis in mice by naturally occurring methylenedioxybenzenes. (Site not responding. Last check: 2007-10-20)
		Isosafrole, safrole, dihydrosafrole, and benzodioxole in vitro also inhibited CYP2E1-dependent metabolism more effectively than eugenol and isoeugenol, whereas PBO did not inhibit CYP2E1 activity.
		The protective effects of isosafrole, safrole, and benzodioxole were therefore predominantly attributed to their ability to inactivate CYP2E1, the major isozyme involved in CCl4 bioactivation.
		Pretreatment with isosafrole, safrole, dihydrosafrole, and benzodioxole at dosages as low as 10 mg/kg significantly prevented the increase in plasma transaminase levels and histochemical changes associated with CCl4-induced liver necrosis, whereas piperonyl butoxide (PBO), eugenol, isoeugenol, sesamol, and curcumin did not prevent CCl4 hepatotoxicity even at 200 mg/kg.
	www.ihop-net.org /UniPub/iHOP/gp/793559.html (218 words)

	The Peracid Oxidation of Isosafrole: A Review - [www.rhodium.ws]
		Formic acid is always present in the solution, often as a solvent, or in any case it is formed from performic acid when it has transferred its extra oxygen atom to the alkene.
		there was a synopsis of an isosafrole oxidation which employed the addition of performic acid to a suspension of sodium carbonate in a solution of isosafrole in dichloroethane and reacting for 5h, in which the yield was given as being 73% of theory.
		Isosafrole (230g, 1.42 mol) was dissolved in 550ml dichloromethane in a 2000ml round-bottomed flask (equipped with a reflux condenser and an addition funnel), and 71g (0.82 mol) NaHCO
	www.erowid.org /archive/rhodium/chemistry/peracid.html (2355 words)

	Erowid Psychoactive Vaults
		For instance, isosafrole was, at the time, a chemical found on the DEA's " 'watch list,' an informal list of chemicals often used illegally which is published to suppliers." [FN1] In addition, the order was far larger than standard orders, which typically do not exceed one kilogram.
		Louisville DEA agents contacted the DEA laboratory in Chicago and were informed that isosafrole is a precursor to the manufacture of 3, 4-methylenedioxyamphetamine ("MDA"), a schedule I hallucinogen under 21 U.S.C. s 812.
		After the isosafrole package had been equipped with a beeper transmitting device, a delivery for the full amount under Riggins's order took place on June 10, 1991.
	de1.erowid.org /freedom/police/dea/dea_info1.html (3321 words)

	Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use - Patent 5422350
		Described is a method of inhibiting the enzymatic metabolism of nitrogen substituted acridines of Formula 1 comprising co-administering with the acridine an effective oxidase inhibiting amount of a P450 1A2 inhibitor.
		The oxidase is one whose activity is induced by beta-naphthaflavone, 3-methylcholanthrene, arochlor, 2,3,7,8-tetrachlorodibenzo-p-dioxin and isosafrole.
		The oxidase inhibitor may be a naphthyridine, a xanthine, a phenoxy amino alkane, a carbamoyl imidazole, a heterocyclic guanidine, or a quinoline.
	www.freepatentsonline.com /5422350.html (5747 words)

	Spectrum Laboratories : Chemical Fact Sheet - Cas # 120581
		Isosafrole occurs naturally as a principal component of the essential oil star anise and
		Isosafrole may biodegrade in natural waters although no data are available concerning the
		biodegradation of isosafrole in culture or in soil and water in the environment.
	www.speclab.com /compound/c120581.htm (666 words)

	Characterization of cytochrome P2-450 (20-S) mRNA. Association with the P1-450 genomic gene and differential response ...
		Association with the P1-450 genomic gene and differential response to the inducers 3-methylcholanthrene and isosafrole.
		P1-450 mRNA induction by 3-methylcholanthrene is measurable in C57BL/6N liver at day 15 of gestation, and the expression becomes enhanced with increasing age.
		Using various subclones as probes, we investigated the differential expression of P1-450 mRNA and P2-450 mRNA induction as a function of association with the Ah locus, 3-methylcholanthrene or isosafrole dosage, tissue specificity, and developmental age.
	www.ihop-net.org /UniPub/iHOP/gp/4313753.html (279 words)

	What is it (Site not responding. Last check: 2007-10-20)
		safrole: 3,4-methylenedioxyallylbenzene, 1-(3,4-methylenedioxyphenyl)-2-propene isosafrole: 3,4-methylenedioxypropenylbenzene, 1-(3,4-methylenedioxyphenyl)-1-propene MDP-2-P: 3,4-methylenedioxyphenyl-2-propanone, 3,4-methylenedioxyphenylacetone, 3,4-methylenedioxybenzyl methyl ketone, piperonylacetone piperonal: 3,4-methylenedioxybenzaldehyde, heliotropin beta-nitroisosafrole: 3,4-methylenedioxyphenyl-2-nitropropene safrole, isosafrole, MDP-2-P, piperonal and beta-nitroisosafrole are the most commonly found precursors to MDMA in clandestine labs.
		The isosafrole is then oxidized into MDP-2-P. This latter procedure has been most clearly presented in _Phenethylamines I Have Known and Loved_ by Alexander Shulgin under synthesis #109 (MDMA).
		The synthesis of MDP-2-P from isosafrole and the aluminum amalgam synthesis are probably the most useful.
	www.extracliprecords.com /xtc.htm (2123 words)

	Section (Site not responding. Last check: 2007-10-20)
		Isosafrole and dihydrosafrole are derivatives of safrole, and have been used as flavoring compounds.
		(c) The analytical method used for detecting safrole, isosafrole and dihydrosafrole is in the ``Journal of the Association of Official Analytical Chemists,'' Volume 54 (Number 4), pages 900 to 902, July 1971, which is incorporated by reference.
		Copies are available from the Division of Food and Color Additives, Center for Food Safety and Applied Nutrition (HFS-200), Food and Drug Administration, 5100 Paint Branch Pkwy., College Park, MD 20740, or available for inspection at the National Archives and Records Administration (NARA).
	a257.g.akamaitech.net /7/257/2422/01apr20051500/edocket.access.gpo.gov/cfr_2005/aprqtr/21cfr189.180.htm (155 words)

	NTP: Executive Summary Sesamol
		The basic moiety of sesamol, safrole, isosafrole, and dihydrosafrole is methylenedioxyphenyl (see below).
		The latter 3 compounds have been shown to be carcinogenic in mice and rats.
		Safrole and isosafrole produced liver tumors following oral administration in rats and mice.
	ntp-server.niehs.nih.gov /index.cfm?objectid=6F604654-F1F6-975E-713C6D8A7F2C7582 (142 words)

	Inducibility of Hepatic CYP1A Enzymes by 3-Methylcholanthrene and Isosafrole Differs in Male Rats Fed Diets Containing ... (Site not responding. Last check: 2007-10-20)
		Western immunoblots illustrating the effects of soy protein isolate (SPI) consumption and induction by 3-methylcholanthrene (3-MC, lanes 2 and 5) and isosafrole (ISO, lanes 3 and 6) on expression of cytochrome P
		Cook J. C., Hodgson E. Induction of cytochrome P450 in congenic C57BL/6J mice by isosafrole: lack of correlation with the Ah locus.
		Shiraki H., Guengerich F. Turnover of membrane proteins: kinetics of induction and degradation of 7 forms of rat liver microsomal cytochrome P450, NADPH-cytochrome P450 reductase and epoxide hydrolase.
	www.nutrition.org /cgi/content/full/131/4/1180 (5341 words)

	Production - Joint Assessment of MDMA Trafficking Trends (Site not responding. Last check: 2007-10-20)
		Although safrole (the primary constituent of sassafras oil), isosafrole, and piperonal are the three primary MDMA precursor chemicals, many production groups are able to acquire MDP2P (3,4-methylenedioxyphenyl-2-propanone), and produce MDMA in a simple conversion process rather than starting the process with one of the precursor chemicals.
		Six of the seven common methods use either safrole or isosafrole; one uses piperonal.
		The Benelux region is attractive to clandestine drug manufacturers and has become the center of MDMA production largely because of well-established precursor chemical routes and easy access to international air and rail transportation hubs.
	www.usdoj.gov /ndic/pubs/642/product.htm (1257 words)

	[No title]
		Piperonal is one of its oxidation products, which can be used as important intermediate in the pharmaceutical synthesis such as L-Dopa and epinephrine, among others, being also helper in insecticides.
		In Brazil, piperonal is usually produced from isosafrole by ozonolysis.
		The present work is based in two main scopes: peroxidase enzyme production by Paecilomyces variotii (IOC-4230) using modified Czapeck-Dox medium and its application in isosafrole biotransformation into piperonal, using hydrogen peroxide as oxidizing agent.
	www.eere.energy.gov /biomass/biotech_symposium/docs/1b-62.doc (354 words)

	Synthesis of 1-ethyl-2-methyl-3-arylindanes. Stereochemistry of five-membered ring formation (Site not responding. Last check: 2007-10-20)
		Such cyclodimer type may also be obtained by formal [3+2] cycloaddition of alcohol derived cation and alkene.
		Isosafrole and isohomogenol dimers with the same configuration behave likewise.
		For isosafrole and isohomogenol, a type Ia approach (Figure 6) offers the advantage of minimising non-bonding interactions and allowing a certain degree of π stacking interaction between aromatic rings.
	www.arkat-usa.org /ark/journal/2003/I10_Rossi-Ruveda/RR-829C/829C.asp (3673 words)

	In vitro formation of an inhibitory complex between an isosafrole metabolite and rat hepatic cytochrome P-450 PB-B -- ...
		In vitro formation of an inhibitory complex between an isosafrole metabolite and rat hepatic cytochrome P-450 PB-B -- Murray and Reidy 17 (4): 449 -- Drug Metabolism and Disposition
		Articles by Murray, M. Articles by Reidy, G. In vitro formation of an inhibitory complex between an isosafrole metabolite and rat hepatic cytochrome P-450 PB-B
		inhibited by isosafrole (I50 = 100 and 110 microM).
	dmd.aspetjournals.org /cgi/content/abstract/17/4/449 (329 words)

	MDMA synthesis (Site not responding. Last check: 2007-10-20)
		To a cooled mixture of 34 g 30% H2O2 and 150 g formic acid, add dropwise a solution of 32.4 g (0.2M) isosafrole in 120 ml acetone, (keep temperature below 30 degrees) Let stand twelve hours and evacuate in vacuum.
		Add 60 ml methanol and 369 g 15% sulfuric acid to the residue and heat on a water bath three hours.
		It is con- verted to isosafrole (a propenyl benzene) by adding equal weight of KOH flakes and absolute ethanol and heating on steam bath or refluxing for 24 hours; dried and evaporated in vacuum or added with two time its volume in water and extracted with ether or methylene chloride and dried, evaporated in vacuum.
	www.links.net /drugz/ex/synthesis.html (464 words)

	Isosafrole-induced cytochrome P2-450 in DBA/2N mouse liver. Characterization and genetic control of induction -- Ohyama ...
		Mouse "cytochrome P2-450" is defined as that form of isosafrole-induced
		isosafrole metabolite formation, yet has no effect on aryl hydrocarbon
		isosafrole is inherited as an autosomal additive trait; studies of
	www.jbc.org /cgi/content/abstract/259/4/2675 (311 words)

	1999 Guideline Manual Information
		Because no new guideline amendments were promulgated in the 1999 amendment cycle, the Commission does not plan to publish a 1999 edition of the Guidelines Manual at this time.
		Commission staff will bring this error to the attention of incoming commissioners so that it may be corrected as soon as possible.
		The line referencing “Isosafrole” should read: “At least 1.44 KG but less than 1.92 KG of Isosafrole;”.
	www.ussc.gov /1999guid/99manual.htm (569 words)

	Safrole, Isosafrole and Dihydrosafrole (Site not responding. Last check: 2007-10-20)
		Safrole and isosafrole are liver carcinogens for the mouse and the rat when administered orally or subcutaneously.
		Dihydrosafrole is carcinogenic for the oesophagus of the rat following oral administration.
		Man may ingest small amounts of safrole and isosafrole through essential oils in which they occur.
	monographs.iarc.fr /htdocs/monographs/vol01/safrole.html (56 words)

	[No title] (Site not responding. Last check: 2007-10-20)
		The present study investigates whether this correlation is maintained with inducing agents known to also increase phase I enzyme activities.
		-naphthoflavone, isosafrole, phenobarbital, ethanol, dexamethasone and clofibric acid regimens in which P450 isozyme induction could be confirmed.
		Comparisons between the responses of mEH, UGT and glutathione S-transferase (GST) activities were made.
	www.elsevier.com /cdweb/journals/03784274/articles/85/1/037842749603633.abstract.en (163 words)

	Etude Sur L'Oxydation De Quelques Substances Insaturees Par L'Acide Perbenzoique et Peracetique (Site not responding. Last check: 2007-10-20)
		We have chosen this substance because it is an example of cis-trans isomerism.
		However, we have only been able to obtain one of the possible isomers of Isosafrole: beta-Isosafrole.
		This agrees with the results of H.I. Waterman & Priester (7) who found that the ordinary transformation of Safrole to Isosafrole, when attempting to prepare alpha-Isosafrole, was incomplete and actually gave a mixture of beta-Isosafrole and Safrole [assuming that alpha-Isosafrole is a benylenic, this makes sense].
	www.flatface.net /~greasyspoon/chemicals/peracetic.html (975 words)

	iqexpand.com (Site not responding. Last check: 2007-10-20)
		Unless sold in a safrole-free form, the roots, bark and extracts made from them may not...
		AM1 calculations of estragole, methyleugenol, safrole, alpha-, andamp;, beta-asarone, elemicin, allylbenzene, eugenol, trans-anethole, isosafrole andamp; myristicin indicate the importance of the carbonium ion...
		Animal carcinogenicity data Safrole and isosafrole are carcinogenic in mice and rats; they produce liver tumours following their oral administration.
	safrole.iqexpand.com (472 words)

	MDP2P from isosafrole via the dibromide, bromohydrin and epoxide (Site not responding. Last check: 2007-10-20)
		It should be noted that the authors have performed the ketone preparation on the anethole and isosafole, but, and this is where it may becomes interesting, it could work for the acid sensitive asarone as well.
		100g Isosafrole is diluted with 100ml petrol ether.
		Under cooling with ice a solution of 100g bromine in 100ml petrol is added drop wise.
	www.flatface.net /~greasyspoon/chemicals/mdp2p.dibromide.html (718 words)

	[No title] (Site not responding. Last check: 2007-10-20)
		In the synthesis of MDA from the ketone it reads H2O2 where it should read H2O -- following the former procedure would be explosive.
		As a side note, this is the same process of making the ketone from isosafrole as Shulgin uses in PiHKAL, thus the synthesis of the ketone is somewhat more verbose than the synthesis of MDA from the ketone.
		Stirring was continued for 16 hours, and care was taken that the slow exothermic reaction did not cause excess heating.
	wsmf.org /textfiles/drugs/mdmasynt.drg (405 words)

	Ecstasy or MDMA (Site not responding. Last check: 2007-10-20)
		Safrole can be extracted from sassafras oil, nutmeg oil, or several other sources.
		The dafrole is them easily isomerized into isosafrole when heated with NaOH or KOH.
		The isasafrole is then oxidized into MDP-2-P. This latter procedure has been most clearly presented in Phenethylamines I Have Known and Loved by Alexander Shuldin under synthesis #109 (MDMA).
	web.elastic.org /~fche/mirrors/www.overthrow.com/ecstasy.html (581 words)

	Safrole, Isosafrole, and Dihydrosafrole (Site not responding. Last check: 2007-10-20)
		Safrole and isosafrole are carcinogenic in mice and rats; they produce liver tumours following their oral administration.
		Safrole also produced liver and lung tumours in male infant mice following its subcutaneous injection.
		No case reports or epidemiological studies were available to the Working Group.
	monographs.iarc.fr /htdocs/monographs/vol10/safrole.html (82 words)

	Selective Involvement of Cytochrome P450 2D Subfamily in In Vivo 4-Hydroxylation of Amphetamine in Rat -- Law et al. 28 ...
		was not affected by the inducers 3-methylcholanthrene, isosafrole,
		Reagents were purchased from the following: isosafrole, 4-nitrophenol, and erythromycin sulfate, Aldrich Chemical Co. (Milwaukee,
		Rats were given inducers as follows: 3-methylcholanthrene (daily 25 mg/kg in corn oil, i.p., 3 days); isosafrole (daily 150
	dmd.aspetjournals.org /cgi/content/full/28/3/348 (3262 words)

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