Α-Ethylmescaline

α-Ethylmescaline (AEM or 3,4,5-trimethoxy-α-ethylphenethylamine) is a lesser-known psychedelic drug. It is an analog of mescaline. AEM was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 220 mg, and the duration unknown.^[1] AEM produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of AEM.

AEM

Names
Preferred IUPAC name 1-(3,4,5-Trimethoxyphenyl)butan-2-amine
Other names 3,4,5-Trimethoxy-α-ethylphenethylamine α-ethyl-3,4,5-trimethoxyphenethylamine α-Ethyl-3,4,5-trimethoxybenzeneethanamine
Identifiers
CAS Number	17097-73-3 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	177522 Y
PubChem CID	204932
UNII	LT8WCD9HNK Y
CompTox Dashboard (EPA)	DTXSID30937911
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 InChI=1/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 Key: DCYONQVUAUEKAJ-UHFFFAOYAD
SMILES COc1c(cc(cc1OC)CC(N)CC)OC O(c1cc(cc(OC)c1OC)CC(N)CC)C
Properties
Chemical formula	C13H21NO3
Molar mass	239.31 g/mol
Legal status	AU: S9 (Prohibited substance)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Derivatives

Shulgin never synthesized further α position-extended mescaline analogues, such as α-propylmescaline (APM) or α-butylmescaline (ABM), as the inactivity of AEM as a psychedelic discouraged him.^[1] 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 as well.^[2]

See also

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