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Safrole

 

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Safrole


 
 

Safrole is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafrasSassafras

Sassafras is a genus of two species of deciduous trees in the family Lauraceae, native to eastern North America and east...
 plants in the form of sassafras oil, or synthesized from other related methylenedioxyMethylenedioxy

Methylenedioxy in the field of chemistry, particularly in organic chemistry, is the name for a functional group with the str...
 compounds. It is the principal component of brown camphorCamphor

| CAS number|[76-22-2][464-49-3]-Camphor)[464-48-2]-Camphor}...
 oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. The Octea cymbarum oil made of the Octea pretiosa,
a plant growing in BrazilBrazil

Brazil, officially the Federative Republic of Brazil , is the largest and most populous country in South America, and ...
, and sassafras oil made of the Sassafras albidumSassafras albidum

Sassafras albidum is a species of Sassafras native to eastern North America, from southern Maine and southern Ontar...
, a plant growing in eastern North AmericaNorth America

North America is a continent in the Earth's northern hemisphere and almost fully in the western hemisphere....
, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma.

It is a precursor in the synthesis of the insecticide synergist piperonyl butoxidePiperonyl butoxide Overview

Piperonyl butoxide is a pesticide synergist....
.

Carcinogenicity

Safrole is a weak carcinogen. It naturally occurs in a variety of spices, for example basil, cinnamon, nutmeg, and pepper. In that role safrole is believed to make a small but measurable contribution to the overall incidence of human cancer. In the US, it was once widely used as a food additive in root beerRoot beer

Root beer is a fermented beverage made from a combination of vanilla, cherry tree bark, licorice root, sarsaparilla root, sa...
, sassafras tea, and other common goods, but was banned by the Food and Drug AdministrationFood and Drug Administration

The Food and Drug Administration is an agency of the United States Department of Health and Human Services and is responsib...
 (FDA) after its carcinogenicity was discovered. Today, safrole is also banned for use in soapSOAP

SOAP is a protocol for exchanging XML-based messages over a computer network, normally using []....
 and perfumePerfume

Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, ob...
s by IFRA.

Use in MDMA manufacture

Safrole is often used as the precursor for the clandestine manufacture of MDMA (ecstasy). The standard synthetic procedure for the production of MDMA from safrole is via isomerization in the presence of a strong base to isosafroleIsosafrole

Isosafrole-1,3-Benzodioxole, or 3,4-methylenedioxyphenyl-1-propene) is an aromatic organic chemical with a smell s...
, oxidation to 3,4-methylenedioxy phenyl-2-propanoneMDP2P

MDP2P is a phenylacetone that has the IUPAC name 3,4-methylenedioxy phenyl-2-propanone....
, finally a reductive aminationReductive amination

Reductive amination is a type of amination reaction which involves the conversion of a carbonyl group to an amine....
 with either methylamineMethylamine

Methylamine is a simple primary amine with a formula of CH3NH2....
 (to make MDMA) or ethylamineEthylamine

Ethylamine is a volatile amine with the molecular structure CH3CH2NH2....
 (to make MDEAMDEA

MDEA, which stands for 3,4-methylenedioxy-N-ethylamphetamine, is a psychedelic hallucinogenic drug and empathogen-entact...
) or ammoniaAmmonia Summary

Ammonia is a compound of nitrogen and hydrogen with the formula NH3....
 (to make MDA3,4-Methylenedioxyamphetamine

h colspan="2" align=center bgcolor="#cccccc">MDA...
). A newer synthesis method makes use of the Wacker processWacker process

The Wacker process or the Hoechst-Wacker process originally referred to the oxidation of ethylene to acetaldehyde by o...
 chloride]] catalyst and 1,4-benzoquinone1,4-Benzoquinone

See also *1,2-benzoquinone*quinonesExternal links ...
) to oxidize safrole directly to the 3,4-methylenedioxy phenyl-2-propanoneMDP2P

MDP2P is a phenylacetone that has the IUPAC name 3,4-methylenedioxy phenyl-2-propanone....
 intermediate.

It is nearly impossible to obtain large quantities of safrole and/or sassafras oil without arousing the suspicion of law enforcement, as both safrole and isosafroleIsosafrole

Isosafrole-1,3-Benzodioxole, or 3,4-methylenedioxyphenyl-1-propene) is an aromatic organic chemical with a smell s...
 as well as piperonalPiperonal

Piperonal is an aromatic aldehyde that comes as a white powder, C8H6O3, and has a floral odor....
 are Category I precursors under regulation No 273/2004 of the European Community. In the US, safrole is currently a List I chemicalDEA list of chemicals

The United States Drug Enforcement Administration maintains lists regarding not only the classification of illicit drugs....
. The root bark of American sassafras contains a few percent of steam volatile oil which is typically 75% safrole. Attempts to access safrole from this source are generally not successful as the yield is low and the effort required to get useful amounts of material is great. Safrole is listed as a Table I under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic SubstancesUnited Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances

The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances is one of three maj...
.

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