Gamma-asarone is an allylbenzene essential oil. It’s the allylbenzene analog of the propenylbenzene alpha-asarone. Both are found in Acorus calamus root although the gamma-asarone content varies considerably and is absent from some varieties.
In vivo, it’s possible that gamma-asarone may form the alkaloid 3-(dimethylamino)-1-(2,4,5-trimethoxyphenyl)propan-1-one (or its piperidine or pyrrolidine counterpart) leading to psychedelic activity. Evidence exists showing that other allylbenzenes such as eugenol, myristicin, safrole, and elemicin form similar alkaloids in vivo.
Acorus calamus root occasionally produces psychedelic effects in some people, although this is rare. These effects are likely attributed to the alkaloid metabolite 3-(dimethylamino)-1-(2,4,5-trimethoxyphenyl)propan-1-one forming from gamma-asarone in vivo. The human body is capable of creating several different metabolites from gamma-asarone, most of which are presumed to be completely inactive. If inactive metabolites are favored in an individual, it’s possible for calamus root to produce no psychedelic effects.
Please see the oilahuasca activation section for more information on allylbenzene activation.
Amphetamine Analog of Gamma-Asarone
The amphetamine form of gamma-asarone is known as 2,4,5-trimethoxyamphetamine. It’s extremely potent, producing stimulant effects and psychedelic effects with as little as 20 mg. The duration of action is from 8-12 hours. It’s possible that the theoretical 3-(dimethylamino)-1-(2,4,5-trimethoxyphenyl)propan-1-one metabolite of gamma-asarone is also active in this dosage range producing similar effects.
|Plant||Origin||Part||Contents of Essential Oil|
|Acorus calamus (European triploid)||Czech||Root||12.52-25.45% |
|Acorus tatarinowii||?||Root||4.51% |
|Aniba hostmanniana||?||Trunk wood||98.6% |
|Aniba hostmanniana||?||Bark||94.5% |
|Asiasarum sieboldi||?||Root||Unspecified |
|Caesulia axillaries||?||?||0-48% |
|Crowea angustifolia var. angustifolia||?||?||68% |
Synonyms: γ-Asarone; Euasarone; Sekishon; Isoasarone; 2,4,5-Trimethoxy-1-allylbenzene; 2,4,5-Trimethoxyallylbenzene; 1-allyl-2,4,5-trimethoxy-benzene; Benzene, 1-(2-propenyl)-2,4,5-trimethoxy; 2,4,5-Trimethoxy-allylbenzene
CAS Number: 5353-15-1
Melting Point: 25 C. Melting point information is based on 1 source for gamma-asarone. This information requires further verification.
Boiling Point: 287.7 °C at 760 mmHg; Another source gives 145-147 C. Boiling point information is very inconsistent for gamma-asarone. Most sources give 287.7 °C. This information needs further verification.
PubChem Compound ID: 636750
Molecular Weight: 208.25364 [g/mol]
Molecular Formula: C12H16O3
H-Bond Donor: 0
H-Bond Acceptor: 3
IUPAC Name: 1,2,4-trimethoxy-5-prop-2-enylbenzene
Canonical SMILES: COC1=CC(=C(C=C1CC=C)OC)OC