3-piperidin-1-yl-1-(3,4,5-trimethoxyphenyl)propan-1-one, referred to as 1'-oxoelemicin-piperidine in this article, is the piperidine alkaloid form of the allylbenzene elemicin produced in vivo after the ingestion of elemicin. This is proven to occur based on several in vivo animals tests.[1]

1'-Oxoelemicin-piperidine is a simple adduct of 1'-oxoelemicin and piperidine. This adduct is likely to form without enzymatic interaction. The closely related 1'-oxosafrole-piperidine adduct forms from 1'-oxosafrole and piperidine by simply mixing the two together, no enzymatic activity is needed. See the article 1'-Oxosafrole for more details.

Instability and Decomposition

1'-Oxoelemicin-piperidine is not very stable. Its prone to decomposition, and easily decomposes during analysis. It decomposes more rapidly than the corresponding 1'-oxosafrole-piperidine and 1'-oxomyristicin-piperidine adducts. Prolonged exposure to air, alkali, silica gel or heat decomposes 1'-oxoelemicin-piperidine into an allylic ketone and piperidine.[1]

Anecdotal Data On Psychedelic Activity

1'-Oxoelemicin-piperidine's action in man is undocumented.

It is likely to have psychoactive properties, but unlikely to have psychedelic action because of the piperidine ring.

It's lipid solubility is very high. It should easily cross the blood brain barrier. However similar compounds with piperidine rings have not been shown to have psychedelic activity in man.

The closely related 1'-oxosafrole-piperidine was shown to antagonize human dopamine D3 receptor sites in vitro. (See the article 1'-Oxosafrole-piperidine for more details). 1'-Oxoelemicin-piperidine might have similar action.

Dozens of anecdotal reports using Oilahuasca Activation techniques for elemicin have consistently shown that piperidine supplementation improves psychedelic activity, and adds a metallic electric feel similar to LSD, while supplements taken to boost levels of dimethylamine weaken psychedelic activity.

It is theorized that supplementation with piperidine causes elemicin to produce more 1'-oxoelemicin-piperidine metabolites and less 1'-oxoelemicin-DMA metabolites in vivo. Why this would lead to stronger psychedelic action is presently unknown.

It is possible that 1'-oxoelemicin-piperidine acts as an enzyme inhibitor protecting 1'-oxoelemicin-DMA from destruction. Some piperidine compounds act as inhibitors of MAO-A, MAO-B, and similar enzymes that might destroy 1'-oxoelemicin-DMA.

Unfortunately tests showing the effects of pure 1'-oxoelemicin-piperidine and 1'-oxoelemicin-DMA in man are currently undocumented.

Chemical Properties

Synonyms: 1'-oxoelemicin-pideridine; 1'-ketoelemicin-pideridine;
PubChem Compound ID: 411263
Molecular Weight: 307.3847 [g/mol]
Molecular Formula: C17H25NO4
XLogP3-AA: 2.3
H-Bond Donor: 0
H-Bond Acceptor: 5
IUPAC Name: 3-piperidin-1-yl-1-(3,4,5-trimethoxyphenyl)propan-1-one
InChI: InChI=1S/C17H25NO4/c1-20-15-11-13(12-16(21-2)17(15)22-3)14(19)7-10-18-8-5-4-6-9-18/h11-12H,4-10H2,1-3H3

See Also

1. E.O. Oswald, L. Fishbein, B.J. Corbett, M.P. Walker. Metabolism of naturally occuring propenylbenzene derivatives : II. Separation and identification of tertiary aminopropiophenones by combines gas—liquid chromatography and chemical ionization mass spectrometry. Journal of Chromatography A, Volume 73, Issue 1, 8 November 1972, Pages 43-57 (web link)
(Download Attached PDF Document) PubMed PMID 5081654
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