Alpha-Asarone
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Alpha-asarone is a propenylbenzene found in Acorus calamus and related herbs.

The aldehyde form of alpha-asarone is 2,4,5-Trimethoxycinnamaldehyde. 2,4,5-Trimethoxycinnamaldehyde and alpha-asarone are closely related to the potent psychedelic TMA-2. For more information on TMA-2 visit Erowid.

2,4,5-Trimethoxycinnamic acid is the major and non toxic metabolite of alpha-asarone.[4]


Psychoactivity

Anecdotal reports indicate that alpha-asarone can have psychoactive-stimulate effects in some individuals, and have no effects in some individuals. Acorus calamus is known for producing very mild psychoactive-stimulant effects, as well as inducing extreme nausea. Some anecdotal reports claim psychedelic activity on occasion from using Acorus calamus, however in most reports, nothing more than mild psychoactive-stimulant effects are reported.

It's possible that a metabolite of alpha-asarone might be psychoactive, and that alpha-asarone is not itself psychoactive.

Both 2,4,5-Trimethoxycinnamaldehyde and alpha-asarone are closely related to the potent psychedelic TMA-2. For more information on TMA-2 visit Erowid.


Effects On Enzymes

In vitro tests show that alpha-asarone inhibits CYP2D6 (IC50 = 55.2 μg/ml), and CYP3A4 (IC50 = 65.2 μg/ml).[3] Note that alpha-asarone appears to have not been clinically tested for enzyme inhibition in human subjects. However, some anecdotal reports indicate that 3 drops of calamus oil is effective as a potent inhibitor of CYP3A4 in humans.


Chemical Properties

Synonyms: α-Asarone; trans-asarone; trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene; trans-1-Propenyl-2,4,5-trimethoxybenzene
PubChem Compound ID: 636822
Molecular Weight: 208.25364 [g/mol]
Molecular Formula: C12H16O3
Melting point: 57-61 ° C(lit.); 62-63 ° C[2]
Boiling point: 296 ° C @ 760 mm Hg[1]
Appearance: Monoclinic needles from water[1]; Needles from light petroleum[2]
Solubility: Practically insoluble in water; soluable in alcohol, ether, glacial acetic acid, carbon tetrachloride, chloroform, petroleum ether[2]
XLogP3: 3
H-Bond Donor: 0
H-Bond Acceptor: 3
IUPAC Name: 1,2,4-trimethoxy-5-[(E)-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-AATRIKPKSA-N
Canonical SMILES: CC=CC1=CC(=C(C=C1OC)OC)OC
Isomeric SMILES: C/C=C/C1=CC(=C(C=C1OC)OC)OC


Bibliography
1. Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-170
2. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 141
3. Metabolism mediated interaction of α-asarone and Acorus calamus with CYP3A4 and CYP2D6;
Fitoterapia. 2011 Apr;82(3):369-74. doi: 10.1016/j.fitote.2010.11.009. Epub 2010 Nov 6; Pandit S, Mukherjee PK, Ponnusankar S, Venkatesh M, Srikanth N; School of Natural Product Studies, Department of Pharmaceutical Technology, Jadavpur University, Kolkata, India; PubMed PMID 21062640
4. 2,4,5-trimethoxycinnamic acid: the major metabolite of alpha-asarone, retains most of the pharmacological properties of alpha-asarone.
Antunez-Solis J, Hernández-Derramadero F, Aquino-Vega M, Ibarra-Ramírez S, Rodríguez-Páez L, Baeza I, Wong C.; J Enzyme Inhib Med Chem. 2009 Jun;24(3):903-9. doi: 10.1080/14756360802318902.; PMID: 18686138; DOI: 10.1080/14756360802318902
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