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. Note that Acorus calamus oil high in beta-asarone appears to have a higher potential of psychoactivity than Acorus calamus oil high in alpha-asarone.
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] These tests showed that Acorus calamus extract was a more potent inhibitor than pure alpha-asarone, indicating that another compound in Acorus calamus, possibly beta-asarone, which wasn't screened for, is a more potent inhibitor.
Acorus calamus, alpha-asarone, and beta-asarone appear not to have 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 (with the oil from Nepal, an oil high in beta-asarone, being the most potent).
Chemical Properties
Synonyms: α-asarone; (E)-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