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.

Natural Sources

Plant Origin Part Contents of Essential Oil
Acorus calamus ? Root 0-3.20%
Acorus calamus (European triploid) Czech Root 12.52-25.45% [7]
Acorus tatarinowii ? Root 4.51% [6][5]
Aniba hostmanniana ? Trunk wood 98.6% [1]
Aniba hostmanniana ? Bark 94.5% [1]
Asiasarum sieboldi ? Root Unspecified [4]
Caesulia axillaries ? ? 0-48% [2]
Crowea angustifolia var. angustifolia ? ? 68% [3]

Chemical Properties

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[8]. 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[8]. 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
XLogP3: 3.1
H-Bond Donor: 0
H-Bond Acceptor: 3
IUPAC Name: 1,2,4-trimethoxy-5-prop-2-enylbenzene
InChI: InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H3

1. O R. Gottlieb and A. I. da Rocha, Phytochem., 11, 000 (1972)
2. Dr. M. Daniel Medicinal Plants: Chemistry and Properties. Science Publishers, 2006, ISBN 1578083958, 9781578083954, Page 70
3. Brophy, J.J.; Goldsack, R.J.; Punruckvong, A.; Forster, P.I.; Fookes, C.J.R. Essential oils of the genus Crowea (Rutaceae). Journal of essential oil research : JEOR (Jul-Aug 1997); ISSN 1041-2905; Vol. No. v. 9(4) p. 401-409
4. Studies on anti-allergic components in the roots of Asiasarum sieboldi.
Hashimoto K, Yanagisawa T, Okui Y, Ikeya Y, Maruno M, Fujita T. PubMed PMID 8202562
5. Simultaneous determination of α-, β- and γ-asarone in Acorus tatarinowii by microemulsion electrokinetic chromatography with [BMIM]PF6 as oil phase.
Wang Y, Li F, Yang FQ, Zuo HL, Xia ZN. PubMed PMID 23158356
6. [Study on GC-MS fingerprint analysis in rhizome of volatile oil of Acorus tatarinowii].
[Article in Chinese] Wei G, Fang YQ, Liu DH, Lin SF. PubMed PMID 15506289
7. The Finnish National Program Supporting Conservation and Use of Plant Genetic Resources on 2003–2008.
Merja Veteläinen. MTT AgriFood Research Finland; 2008; ISBN 978-952-487-207-2; ISSN 1458-5103 Download Attached PDF Document
8. Dictionary of Organic Compounds: Phl - Z : P-0-02797 - Z-0-00015, Volume 6.
J. Buckingham; CRC Press, 1996; ISBN 0412540908, 9780412540905
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