Beta-3′-Oxoasarone
beta-3′-oxoasarone.png

Beta-3′-Oxoasarone is the aldehyde form of beta-asarone and the cis isomer of 2,4,5-Trimethoxycinnamaldehyde. It is a metabolite of beta-asarone that's formed in human liver.[4]


Psychoactivity

A metabolite of beta-asarone is the reason Acurus calamus is known in some cultures as a psychedelic. However, not all Acorus calamus contains sufficient quantities of beta-asarone to be effective. Acorus calamus from Nepal typically contains a large amount of beta-asarone. Acorus calamus from India usually contains very little beta-asarone, and will cause extreme nausea before doses high enough to get some minor effects from beta-asarone are ingested.

It's important to note that beta-asarone itself is not active. One of it's metabolites can produce psychedelic effects in man. Not everyone's body metabolizes beta-asarone the same way, leading to different results for different individuals. Some people are not able to experience psychedelic effects from ingesting beta-asarone. This is because their bodies do not produce enough of the active metabolite to experience effects.

The active metabolite of beta-asarone is currently unidentified. There has been speculation of it being an amphetamine, but that has been disproven.

Many human tests show that beta-asarone in some people can be activated via several Oilahuasca formulas, and can even be activated naturally without combining it with other compounds. It's fairly easy to activate with doses as small as 1 drop having effects in some people, and it works in a high percentage of people, producing LSD-like effects. This activity is more typical of allylbenzenes rather than Propenylbenzens.

Beta-asarone's aldehyde metabolite, beta-3′-oxoasarone, is likely the metabolite that eventually leads to activity. As an aldehyde it should theoretically easily form adducts with amino acids, and other mines, potentially leading to psychedelic activity.


Possible Adduct Formation

Aldehydes, such as the very closely related cinnamaldehyde, are known to easily form adducts with many compounds. Cinnamaldehyde can, for example, form adducts with simple amino acids, at room temperature without any catalysts.[2][3] It's unknown which adducts are possible with beta-3′-oxoasarone, but the chemical bears such a striking similarity to cinnamaldehyde, that it's likely a lot of adducts that are possible with cinnamaldehyde are also possible with beta-3′-oxoasarone.

See the article Cinnamaldehyde for more information on aldehyde adducts.

Beta-3′-oxoasarone Cinnamaldehyde
beta-3′-oxoasarone.png cinnamaldehyde.png

Natural Sources

Beta-3′-Oxoasarone (Cis-2,4,5-trimethoxycinnamaldehyde) has been isolated from Acorus Calamus[1].


Chemical Properties

Synonyms: cis-2,4,5-Trimethoxycinnamaldehyde; (Z)-3-(2,4,5-Trimethoxyphenyl)-2-propenal; (2Z)-3-(2,4,5-Trimethoxyphenyl)acrylaldehyde
Melting Point: 85[1]
Appearance: fine needles[1]
PubChem Compound ID: 46906714
ChemSpider ID: 25028478
Molecular Weight: 222.23716 g/mol
Molecular Formula: C12H14O4
XLogP3: 1.9
IUPAC Name: (Z)-3-(2,4,5-trimethoxyphenyl)prop-2-enal
InChI: InChI=1S/C12H14O4/c1-14-10-8-12(16-3)11(15-2)7-9(10)5-4-6-13/h4-8H,1-3H3/b5-4-
InChI Key: DNAVOCNYHNNEQI-PLNGDYQASA-N
Canonical SMILES: COC1=CC(=C(C=C1C=CC=O)OC)OC
Isomeric SMILES: COC1=CC(=C(C=C1/C=C\C=O)OC)OC
CAS No.: 99217-07-9

Bibliography
1. Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients
Shmuel Yannai; CRC Press, 2003; ISBN 1420068458, 9781420068450
2. The antimicrobial activities of the cinnamaldehyde adducts with amino acids.
Wei QY, Xiong JJ, Jiang H, Zhang C, Wen Ye. PubMed PMID: 21856030 DOI: 10.1016/j.ijfoodmicro.2011.07.034 (Download Attached PDF Document)
3. Arthur D. Little
SUPPORT FOR CHEMICAL NOMINATION AND SELECTION PROCESS OF THE NATIONAL TOXICOLOGY PROGRAM, EXECUTIVE SUMMARY OF DATA, CINNAMALDEHYDE; DECEMBER 14, 1989 (Download Attached PDF Document)
4. Hepatic metabolism of carcinogenic β-asarone.
Cartus AT, Stegmüller S, Simson N, Wahl A, Neef S, Kelm H, Schrenk D. PubMed PMID: 26273788; DOI: 10.1021/acs.chemrestox.5b00223
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