3,4,5-Trimethoxyphenoxyethylamine

3,4,5-Trimethoxyphenoxyethylamine is a chemical compound of the phenoxyethylamine family related to the psychedelic phenethylamine mescaline.^[1]^[2]^[3]^[4] It is the analogue of mescaline in which an oxygen atom has been inserted between the benzene ring and the ethylamine side chain.^[1]^[2]^[3]^[4] The drug was tested in humans at doses of 10 to 300 mg orally but was found to be inactive.^[1]^[2]^[3]^[4] For comparison, mescaline is active at doses as low as 100 mg orally.^[5]^[6]^[7] 3,4,5-Trimethoxyphenoxyethylamine was first described and studied by A. Carlsson and colleagues in 1963.^[4] It was subsequently reviewed by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and other publications.^[1]^[2]^[3]

Other names2-(3,4,5-Trimethoxyphenoxy)ethylamine; 3,4,5-TMPhOEA

CAS Number

65876-17-7

PubChem CID

3028345

ChemSpider

2293772

Quick facts Clinical data, Other names ...

3,4,5-Trimethoxyphenoxyethylamine
Clinical data

Other names	2-(3,4,5-Trimethoxyphenoxy)ethylamine; 3,4,5-TMPhOEA
Identifiers
IUPAC name 2-(3,4,5-trimethoxyphenoxy)ethanamine
CAS Number	65876-17-7
PubChem CID	3028345
ChemSpider	2293772
CompTox Dashboard (EPA)	DTXSID60388654
Chemical and physical data
Formula	C₁₁H₁₇NO₄
Molar mass	227.260 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC(=CC(=C1OC)OC)OCCN
InChI InChI=1S/C11H17NO4/c1-13-9-6-8(16-5-4-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3 Key:AFJZAAPPTLXGHC-UHFFFAOYSA-N

References

[1]
Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "One additional manipulation with some of these [mescaline-related] structures has been made and should be mentioned. These are the analogues with an oxygen atom inserted between the aromatic ring and the aliphatic chain. They are, in essence, aminoethyl phenyl ethers. The first is related to mescaline itself, 2-(3,4,5-trimethoxyphenoxy)ethylamine. Human trials were conducted over the dose range of 10 to 300 milligrams and there were no effects observed. The second is related to trichocerine, N,N-dimethyl-2-(3,4,5-trimethoxyphenoxy)ethylamine. It was inactive in man over the range of 10 to 400 milligrams. Mescaline, at a dose of 420 milligrams, served as the control in these studies."
[2]
Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 2.2.7. β-(3,4,5-Trimethoxyphenoxy)-ethylamine In a study of structural analogs of mescaline, Carlsson et al. (1963) prepared the ethanolamine ether β-(3,4,5-trimethoxyphenoxy)ethylamine (28.1) and the N,N-dimethyl homolog. Again, neither compound is strictly a N-substituted derivative of mescaline, but their close structural similarity, and the fact that they have been assayed in man, makes their inclusion here desirable. The toxicity of (28.1) was determined in the mouse to be 500 mg/kg (LD50, i.p.). In a series of human trials (from 10 to 300 mg dosages), (28.1) was found to be without central effects (mescaline was the control drug, at a 420-mg dose).
[3]
Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. Modifications on the chain portion of the mescaline molecule are known. The insertion of an oxygen atom between the chain and the aromatic ring to give 60.20 eliminates the hallucinogenic activity (77), as does the homologation at the nitrogen either to the monomethyl (78) or to the dimethyl homolog trichocerine (60.21; 76, 79, 80).
[4]
Carlsson A, Corrodi H, Magnusson T (1963). "Basische Derivate des 4,5,6-Trimethoxyindols und des 3,4,5-Trimethoxyphenols". Helvetica Chimica Acta. 46 (4): 1231–1235. doi:10.1002/hlca.19630460418. ISSN 0018-019X. Retrieved 21 November 2025.
[5]
Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biological Psychiatry. Cognitive Neuroscience and Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
[6]
Liechti ME, Holze F (2022). "Dosing Psychedelics and MDMA". Disruptive Psychopharmacology. Curr Top Behav Neurosci. Vol. 56. pp. 3–21. doi:10.1007/7854_2021_270. ISBN 978-3-031-12183-8. PMID 34734392.
[7]
Klaiber A, Schmid Y, Becker AM, Straumann I, Erne L, Jelusic A, et al. (September 2024). "Acute dose-dependent effects of mescaline in a double-blind placebo-controlled study in healthy subjects". Translational Psychiatry. 14 (1) 395. doi:10.1038/s41398-024-03116-2. PMC 11442856. PMID 39349427.

3,4,5-Trimethoxyphenoxyethylamine

See also

References

External links

Related Articles

Related Articles

"Basische Derivate des 4,5,6-Trimethoxyindols und des 3,4,5-Trimethoxyphenols"

"Dosing Psychedelics and MDMA"

"Acute dose-dependent effects of mescaline in a double-blind placebo-controlled study in healthy subjects"