Oilahuasca Activation Sequence B

SEQUENCE B

Please note that steps 1-3 are proven to occur for some allylbenzenes such as methyl eugenol. Step 4 is purely theoretical. These sequences will lead to similar alkaloids as produced in sequence A, but the alkaloids theoretically produced by sequence B all have higher XLogP values and should therefor have stronger psychoactivity.

SEQUENCE B - STEP 1: ORAL INGESTION (OR TOPICAL APPLICATION)

Elemicin is ingested orally (or applied topically to the skin).
Elemicin-UP.gif

SEQUENCE B - STEP 2: CONVERSION TO AN ALCOHOL

Elemicin is 3'-hydroxylated to the alcohol 3'-hydroxyisoelemicin. The enzymes responsible for this action are currently unknown but theorized to be CYP2C9 and CYP2E1.

3-hydroxy-isoelemicin.png

SEQUENCE B - STEP 3: CONVERSION TO AN ALDEHYDE

3'-Hydroxyisoelemicin is oxidized to the aldehyde 3,4,5-Trimethoxycinnamaldehyde possibly by 17bHSD2, CYP2E1, or alcohol dehydrogenase.

3_4_5-Trimethoxycinnamaldehyde.png

SEQUENCE B - STEP 4: CONVERSION TO ALKALOIDS

The alkaloids in this section are purely theoretical but based on strong evidence of their transient existence in animals.

3-(3,4,5-Trimethoxyphenyl)propionic acid is a metabolite of elemicin found in rat urine. 3-(3,4,5-Trimethoxyphenyl)propionic acid is a product that would form from the action of monamine oxidase enzymes on 1-(3,4,5-trimethoxycinnamoyl)dimethylamine, indicating that 1-(3,4,5-trimethoxycinnamoyl)dimethylamine formed in the rats but was enzymatically converted to 3-(3,4,5-trimethoxyphenyl)propionic acid before being excreted into the urine.

The following three alkaloids are theorized to be possible active metabolites of elemicin made from it's aldehyde metabolite 3,4,5-trimethoxycinnamaldehyde and the endogenous amines dimethylamine, piperidine, and pyrrolidine.

3,4,5-Trimethoxycinnamaldehyde may condense with dimethylamine to form the theoretical alkaloid metabolite 1-(3,4,5-Trimethoxycinnamoyl)dimethylamine.
1_3-4-5-Trimethoxycinnamoyl_dimethylamine.png

3,4,5-Trimethoxycinnamaldehyde may condense with piperidine to form the theoretical alkaloid metabolite 1-(3,4,5-Trimethoxycinnamoyl)piperidine.
1_3-4-5-Trimethoxycinnamoyl_piperidine.png

3,4,5-Trimethoxycinnamaldehyde may condense with pyrrolidine to form the theoretical alkaloid metabolite 1-(3,4,5-Trimethoxycinnamoyl)pyrrolidine.
1_3-4-5-Trimethoxycinnamoyl_pyrrolidine.png

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