Beta-Asarone
beta-asarone.png

Note that most of the facts available currently for beta-asarone are primarily obtained from in vitro tests using animal and human tissue, or in vivo tests performed only on animals. It's important to note that data collected from in vivo tests perform on animals and data from in vitro studies, even those using human tissues, can differ dramatically from real world results obtained from in vivo tests done with actual living human beings. Unfortunately, very few clinical test performed on actual human beings exist for beta-asarone.

Beta-asarone is a propenylbenzene found in Acorus calamus and related herbs. Calamus oil from Nepal is very high in beta-asarone.

Beta-asarone is an isomer of alpha-asarone in which the tail is bent inward towards the benzene ring. The aldehyde form of beta-asarone is Cis-2,4,5-Trimethoxycinnamaldehyde.


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. 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, and their potassium forms (such as potassium glycinate), at room temperature without any catalysts.[8][9] 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.


Use in Oilahuasca

Anecdotal reports indicate that beta-asarone is an extremely powerful admixture to use in Oilahuasca formulas, helping activate most allylbenzenes, especially elemicin which is tough to activate. The exact reason for this is currently unknown. It's addition to nearly all Oilahuasca formulas will greatly increase the chances of successful activation. As little as 1 drop (about 10-20 mg) is extremely effective. It has isn't own effects at 1 drop, but they are minor, and won't color up the experience much.


Cancer Fighting Action

Beta-asarone has been found to be effective in fighting certain forms of cancer. Beta-asarone effectively inhibits the proliferation of human gastric cancer cells.[1] It also suppress the growth of colon cancer.[4]


Nootropic Effects

Beta-asarone improves learning and memory.[6] It also alleviates depression.[2]


Neuroprotective Effects

Beta-asarone shows neuroprotective effects against dopamine-induced neurotoxicity.[3] Beta-asarone may also help fight cognitive impairment associated with conditions such as Alzheimer's disease.[5]


Possible Metabolites of Beta-Asarone

No clinical tests on human subjects examining the full metabolites of beta-asarone exist. In vitro tests using liver microsomes of humans have given some light as to what might occur in humans. In human liver microsomes, 71-75% of beta-asarone was metabolized into beta-asarone-1',2'-erythro-diol, beta-asarone-1',2'-threo-diol, and the ketone 2,4,5-trimethoxyphenylacetone via a theoretical transient epoxidation step.[7]

Epoxidation Route
beta-asarone Beta-asarone-1′,2′-epoxide1 Beta-asarone-1',2'-erythro-diol beta-asarone-1',2'-threo-diol 2,4,5-trimethoxyphenylacetone
beta-asarone.png beta-asarone-1′,2′-epoxide.png beta-asarone-1',2'-erythro-diol.png beta-asarone-1',2'-threo-diol.png 2,4,5-trimethoxyphenylacetone.png
Synonyms: 2-(2,4,5-Trimethoxyphenyl)-3-methyloxirane; 2-methyl-3-(2,4,5-trimethoxyphenyl)oxirane
PubChem CID: 101689827
Synonyms: (1R,2R)-1-(2,4,5-Trimethoxyphenyl)-1,2-propanediol; 1,2-Propanediol, 1-(2,4,5-trimethoxyphenyl)-, (1R,2R)-
ChemSpider ID: 9497404
Synonyms: (1R,2S)-1-(2,4,5-Trimethoxyphenyl)-1,2-propanediol; 1,2-Propanediol, 1-(2,4,5-trimethoxyphenyl)-, (1R,2S)-
ChemSpider ID: 9599894
Synonyms: Acoramone; 1-(2,4,5-trimethoxyphenyl)propan-2-one;
PubChem CID: 3083746

21-15% of the beta-asarone was metabolized via hydroxylation, forming 1′-hydroxyasarone, beta-3'-hydroxyasarone and small amounts of beta-3'-oxoasarone.[7]

Hydroxylation Routes
beta-asarone 1′-Hydroxyasarone Beta-3'-hydroxyasarone Beta-3′-oxoasarone
beta-asarone.png 1′-hydroxyasarone.png beta-3′-hydroxyasarone.png beta-3′-oxoasarone.png
Synonyms: 1-(2,4,5-Trimethoxyphenyl)-2-propen-1-ol
ChemSpider ID: 37615873
Synonyms: (2Z)-3-(2,4,5-Trimethoxyphenyl)-2-propen-1-ol
ChemSpider ID: 28525828
Synonyms: (2Z)-3-(2,4,5-Trimethoxyphenyl)acrylaldehyde
ChemSpider ID: 25028478

8-10% was metabolized via demethylation.[7]

Demethylation Routes
beta-asarone 6-demethyl-beta-asarone 4-demethyl-beta-asarone 3-demethyl-beta-asarone
beta-asarone.png 6-demethyl-beta-asarone.png 4-demethyl-beta-asarone.png 3-demethyl-beta-asarone.png

6-demethy-beta-asarone.png


Chemical Properties

Synonyms: β-asarone; (Z)-asaronel cis-asarone
Melting Point: 57-61 ° C; 62-63 ° C @ 760 mmHg. This information needs further verification. This information is suspected of being incorrect because calamus oil high in beta-asarone does not crystallize on standing at room temperature. Many sources confuse alpha-asarone for beta-asarone. Alpha-asarone is a solid at room temperature. One source states that beta-asrone is a colorless to pale yellow clear liquid, indicating that the melting point is far below room temperature (21 C).
Boiling Point: 296 °C at 760 mmHg. A few sources state 264-267 ° C @ 760 mmHg; This information needs further verification.
PubChem Compound ID: 5281758
Molecular Weight: 208.25364 [g/mol]
Molecular Formula: C12H16O3
XLogP3: 3
H-Bond Donor: 0
H-Bond Acceptor: 3
IUPAC Name: 1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
InChI: InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,
1-4H3/b6-5-
InChIKey: RKFAZBXYICVSKP-WAYWQWQTSA-N
Canonical SMILES: CC=CC1=CC(=C(C=C1OC)OC)OC
Isomeric SMILES: C/C=C\C1=CC(=C(C=C1OC)OC)OC
CAS #: 5273-86-9


Bibliography
1. β-Asarone inhibits gastric cancer cell proliferation.
Wu J, Zhang XX, Sun QM, Chen M, Liu SL, Zhang X, Zhou JY, Zou X. PubMed PMID: 26502896; DOI: 10.3892/or.2015.4316
2. β-asarone from Acorus gramineus alleviates depression by modulating MKP-1.
Sun YR, Wang XY, Li SS, Dong HY, Zhang XJ. PubMed PMID: 25966222; DOI: 10.4238/2015.May.4.7
3. Neuroprotective Effects of β-Asarone Against 6-Hydroxy Dopamine-Induced Parkinsonism via JNK/Bcl-2/Beclin-1 Pathway.
Zhang S, Gui XH, Huang LP, Deng MZ, Fang RM, Ke XH, He YP, Li L, Fang YQ. PubMed PMID: 25404088; DOI: 10.1007/s12035-014-8950-z
4. Beta-asarone induces LoVo colon cancer cell apoptosis by up-regulation of caspases through a mitochondrial pathway in vitro and in vivo.
Zou X, Liu SL, Zhou JY, Wu J, Ling BF, Wang RP. PubMed PMID: 23244151;
5. Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats.
Geng Y, Li C, Liu J, Xing G, Zhou L, Dong M, Li X, Niu Y. PubMed PMID: 20460763;
6. β-asarone improves learning and memory and reduces Acetyl Cholinesterase and Beta-amyloid 42 levels in APP/PS1 transgenic mice by regulating Beclin-1-dependent autophagy.
Deng M, Huang L, Ning B, Wang N, Zhang Q, Zhu C, Fang Y. PubMed PMID: 27737765; DOI: 10.1016/j.brainres.2016.10.008
7. 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
8. 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)
9. 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)
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