Table of Contents
Safrole is the main component of sassafras essential oil and a minor component of nutmeg essential oil. It is an allylbenzene. Used without proper Oilahuasca Activation techniques it only produces mild sedative effects. It has produced psychedelic effects in a few individuals when used with proper Oilahuasca Activation techniques.
|Plant||Origin||Part||Contents of Essential Oil|
|Piper auritum||Panama||Leaves||70% |
|Sassafras albidum||Root Bark||80-85%|
Effects on Cytochrome P450 Enzymes
The Carcinogenicity Myth
No evidence exists for sassafras tea or safrole ingestion causing cancer in humans.
In humans, the close amphetamine relative of safrole, MDMA has been shown to protect against cancer formation.
The very closely related allylbenzene myristicin has also shown anti-cancer properties. A 65% inhibition of the tumor multiplicity in the lung was observed as the result of treatment of myristicin in rats.
Animal in vitro tests determined safrole to act as a possibly weak carcinogen, but human tests have not shown this to be the case. Animal tests showing potential carcinogenicity were enough for it to be banned for use in food in the USA, despite no evidence of human carcinogenicity.
The main metabolite of safrole leading to possibly carcinogenicity in rats is 1-hydroxysafrole after SULT metabolism to its sulfate conjugate. However, this metabolite has not been detected in humans after the oral ingestion of safrole using the same tests that found it occurred in rats.
Its believed that the banning of safrole, despite a total lack of evidence of it being carcinogenic in humans, and it's close relatives actually showing anti-cancer effects in vivo, was a move to prevent the sale of safrole because of its use in the manufacture of the illegal drug MDMA.
Non-Alkaloid Metabolites Found in Humans
These metabolites are created in vivo by humans after ingestion of safrole. Human P450 enzymes are responsible for their creation.
Hydroxychavicol (also known as 1,2-dihydroxy-4-allylbenzene) is the main metabolite of safrole found in human urine (up to 65%) after the ingestion of pure safrole.
This metabolite is an allylbenzene and could potentially be converted to an alkaloid in vivo in humans producing possible activity. The predicted action of this compound as an alkaloid is stimulation without psychedelic activity because it lacks a methoxy group on the benzene ring.
The allylbenzene eugenol occurs as a very minor metabolite in human urine after ingestion of pure safrole.
The allylbenzene chavibetol (also known as 1-methoxy-2-hydroxy-4-allylbenzene) occurs as a very minor metabolite in human urine after ingestion of pure safrole.
Non-Alkaloid Metabolites Found in Rats
1'-Oxosafrole is a metabolite made from safrole's metabolite 1'-hydroxysafrole.
This metabolite, although not yet found to occur in human urine, is presumed to be created in humans, but rapidly metabolized.
Hydroxychavicol is the main metabolite of safrole found in rat urine after the ingestion of pure safrole.
The allylbenzene chavibetol (also known as 1-methoxy-2-hydroxy-4-allylbenzene) occurs as a very minor metabolite in rat urine after ingestion of pure safrole.
Tests performed in rats found this metabolite occurred in urine after oral ingestion of safrole as a minor metabolite. This metabolite could not be detected in urine samples of human test subjects after the ingestion of pure safrole.
According to one human in vitro study the P450 enzymes CYP2C9 and CYP2E1, and to a lesser degree CYP2A6 and CYP2D6, play a role in oxidizing the allylbenzene safrole into 1'-hydroxysafrole. It's possible that this metabolite is created in humans but metabolized completely shortly after creation.
Tests performed in rats found this metabolite occurred in urine after oral ingestion of safrole as a minor metabolite, but not in human urine.
Safrole is proven to produce dimethylamine, piperidine, and pyrrolidine alkaloids as very minor metabolites after oral or topical use. They are believed to be adducts that form from 1'-oxosafrole. They are presumed to be psychoactive, and to contribute to the effects of nutmeg as sassafras.
3-N,N-Dimethylamino-1-(3,4-methylenedioxyphenyl)-1-propanone is the dimethylamine adduct of 1'-oxosafrole.
3-Piperidino-1-(3,4-methylenedioxyphenyl)-1-propanone is the piperidine adduct of 1'-oxosafrole.
3-Pyrrolidino-1-(3,4-methylenedioxyphenyl)-1-propanone is the pyrrolidine adduct of 1'-oxosafrole.
Compound ID: 5144
Molecular Weight: 162.1852 [g/mol]
Molecular Formula: C10H10O2
Appearance: Colorless or pale yellow oil; colorless liquid, prisms, or crystals
Boiling Point: 234.5 deg C
Melting Point: 11.2 deg C
Solubility: Soluble in alcohol; slightly soluble in propylene glycol; insoluble in water, glycerol; Miscible with chloroform, ether
IUPAC Name: 5-prop-2-enyl-1,3-benzodioxole
Canonical SMILES: C=CCC1=CC2=C(C=C1)OCO2