Α-Ethylmescaline

Î±-Ethylmescaline (AEM or 3,4,5-trimethoxy-Î±-ethylphenethylamine) is a chemical compound of the phenethylamine and phenylisobutylamine families related to the psychedelic drug mescaline.^[1]^[2]^[3] It is the analogue of mescaline and TMA with an ethyl group at the Î± position of the side chain.^[1]^[2]

Other namesAEM; 3,4,5-Trimethoxy-Î±-ethylphenethylamine; Î±-Ethyl-3,4,5-trimethoxyphenethylamine;

ATC code

None

Legal status

AU: S9 (Prohibited substance)

Onset of actionUnknown^[1]

Quick facts Clinical data, Other names ...

AEM
Clinical data


Other names	AEM; 3,4,5-Trimethoxy-Î±-ethylphenethylamine; Î±-Ethyl-3,4,5-trimethoxyphenethylamine;
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance)
Pharmacokinetic data
Onset of action	Unknown^[1]
Duration of action	Unknown^[1]
Identifiers
IUPAC name 1-(3,4,5-trimethoxyphenyl)butan-2-amine
CAS Number	17097-73-3^Y
PubChem CID	204932
ChemSpider	177522^Y
UNII	LT8WCD9HNK
CompTox Dashboard (EPA)	DTXSID30937911
Chemical and physical data
Formula	C₁₃H₂₁NO₃
Molar mass	239.315 gÂ·mol^â1
3D model (JSmol)	Interactive image
SMILES COc1c(cc(cc1OC)CC(N)CC)OC
InChI InChI=1S/C13H21NO3/c1-5-10(14)6-9-7-11(15-2)13(17-4)12(8-9)16-3/h7-8,10H,5-6,14H2,1-4H3^Y Key:DCYONQVUAUEKAJ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Use and effects

In his book PiHKAL, Alexander Shulgin lists AEM's dose as greater than 220 mg orally and its duration as unknown.^[1]^[2] It was found to be completely inactive in terms of both central and peripheral effects in humans.^[1]^[2]^[3]^[4]

Chemistry

Synthesis

The chemical synthesis of AEM has been described.^[1]

Derivatives

Alexander Shulgin never synthesized further Î± position-extended mescaline analogues, such as Î±-propylmescaline (APM) or Î±-butylmescaline (ABM), as the inactivity of AEM in humans discouraged him.^[1]^[2] In any case, APM and ABM have been found to be inactive in terms of induction of the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may be non-hallucinogenic in humans as well.^[5]

History

AEM was first described in the scientific literature by Alexander Shulgin by 1963.^[4] He tested it and found it to be inactive in 1961.^[6] Later, Shulgin described AEM in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

References

[1]
Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal001.shtml
[2]
Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67â137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. In the case of TMA, a continuous extension of this alpha-group led to the alpha-ethyl homologue alpha-ethylmescaline (AEM) which showed no human activity at over 200mg, and the longer-chained homologues were not evaluated. This alpha-homologation is discussed below for some of the 2,4,5-trisubstituted analogues.
[3]
Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46â58. PMID 4576313. Archived from the original on 2025-07-12. The actions of a compound that results from the combination of the features of mescaline and of amphetamine have been described (24). This compound is 3,4,5-trimethoxyamphetamine (3,4,5-trimethoxyphenylisopropylamine, TMA, 13) and it has been established as being an effective sensory distorting agent at levels of about 175 mg (25). It is thus about twice as potent as mescaline.3 An extension of this chain to the 4-carbon homolog (alpha-ethylmescaline, 14) produces a compound that lacks all central and peripheral activity in human subjects at acute levels as high as 220 mg (27). These several chemicals have laid the groundwork for all of the substances to be discussed below, namely that the three carbon chain, the phenylisopropylamine or amphetamine structure, has proved to be optimum for the generation of these sensory distortion effects. A decrease of the chain length to two carbons (the loss of the alpha-methyl group) usually retains the nature of activity but with some decrease in potency. A lengthening of the chain to four carbons (the substitution of an alpha-ethyl group) changes the qualitative nature of the pharmacological response.
[4]
Shulgin AT (March 1963). "Psychotomimetic agents related to mescaline". Experientia. 19: 127â128. doi:10.1007/BF02171586. PMID 13988773. In human subjects, the potency of trimethoxyamphetamine (I, R = CH3) has been established as over twice that of mescaline2. Evaluation of the immediate homologue, Î±-ethyl mescaline (I, R = ethyl) at oral levels in excess of 2.5 mg/kg (as the free base), produced neither central activity nor psychic disturbance, thus demonstrating a psychotomimetic potency of less than half that of trimethoxyamphetamine, and suggesting that three carbons represent an optimum chain length.
[5]
Corne SJ, Pickering RW (1967). "A possible correlation between drug-induced hallucinations in man and a behavioural response in mice". Psychopharmacologia. 11 (1): 65â78. doi:10.1007/BF00401509. PMID 5302272.
[6]
"Sub-acute oral effects â AEM" (PDF). 1961-03-05. Archived from the original (PDF) on 2025-04-15.