3,4,5-Trimethoxycinnamaldehyde
3,4,5-Trimethoxycinnamaldehyde.png

3,4,5-Trimethoxycinnamaldehyde, also known as 3'-oxoelemicin, is a theoretical metabolite of elemicin. As an aldehyde, it should be able to form adducts easily just like the closely related cinnamaldehyde can. This can easily lead to alkaloid formation in vivo, giving rise to potential psychedelic activity.


Psychoactivity

According to the Oilahuasca Activation Theory a metabolite of elemicin has psychedelic effects in humans, similar to mescaline, but it can be difficult to coerce the human body to create the metabolite. Oilahuasca Activation techniques have been created to attempt to force the body to create the psychedelic metabolite. There has been some success in this area of research, however some people's bodies still fail to generate the psychedelic metabolite. At this time, the actual psychedelic metabolite's identity is unknown. There are several potential candidates for the identity of the psychedelic metabolite of elemicin. An early theory was that an amphetamine-like metabolite was created in humans, but that was proven false.

3,4,5-Trimethoxycinnamaldehyde is very likely the intermediate elemicin metabolite that eventually leads to psychedelic activity when elemicin is properly activated. Being an aldehyde, it should easily form alkaloids in vivo, but this greatly complicates things. It should be capable of forming hundreds of different alkaloids in vivo. Without knowing which elemicin metabolite is psychedelic, it's like finding a needle in a haystack. While current Oilahuasca Activation techniques are getting pretty good at creating the psychedelic metabolite for some people, not knowing the exact identity of the psychedelic metabolite that's needed, makes it difficult to create an Oilahuasca Activation technique that specifically targets the intended metabolite.

Current Oilahuasca Activation techniques work by inhibiting and inducing certain enzymes in the human body. They do not as of yet work to force the correct alkaloid to form, which is the very last step. They help to prevent inactivation, but don't help with the final alkaloid step. This is a big flaw, and likely the cause of many people failing to get effects from elemicin despite using some of the most effective current Oilahuasca Activation techniques.


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][1] It's unknown which adducts are possible with 3,4,5-Trimethoxycinnamaldehyde, 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 3,4,5-Trimethoxycinnamaldehyde.

See the article Cinnamaldehyde for more information on aldehyde adducts.

3,4,5-Trimethoxycinnamaldehyde Cinnamaldehyde
3,4,5-Trimethoxycinnamaldehyde.png cinnamaldehyde.png

Chemical Properties

Synonyms: 3'-oxoelemicin
PubChem Compound ID: 36798
Molecular Weight: 222.23716 [g/mol]
Molecular Formula: C12H14O4
XLogP3: 1.3
H-Bond Donor: 0
H-Bond Acceptor: 4
IUPAC Name: 3-(3,4,5-trimethoxyphenyl)prop-2-enal
InChI: InChI=1S/C12H14O4/c1-14-10-7-9(5-4-6-13)8-11(15-2)12(10)16-3/h4-8H,1-3H3
InChIKey: XDSHNNRBLSBDAP-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C=CC=O

Bibliography
1. 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)
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)
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