Α-Ethylmescaline

α-Ethylmescaline (AEM or 3,4,5-trimethoxy-α-ethylphenethylamine) is a chemical compound of the phenethylamine family related to the psychedelic drug mescaline.^[1][2][3]

AEM

Clinical data
Other names	AEM; 3,4,5-Trimethoxy-α-ethylphenethylamine; α-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 g·mol−1
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

Derivatives

Alexander Shulgin never synthesized further α position-extended mescaline analogues, such as α-propylmescaline (APM) or α-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]

See also

• Substituted mescaline analogue
• α-Methylmescaline (3,4,5-TMA)
• Ariadne (drug) (α-ethyl-DOM)