2,5-Dimethoxy-4-ethoxyamphetamine

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.^[1] It was first described by Alexander Shulgin by 1968.^[2]

MEM

Clinical data
Other names	2,5-Dimethoxy-4-ethoxyamphetamine; 4-Ethoxy-2,5-dimethoxyamphetamine; MEM
Routes of administration	Oral[1]
Drug class	Serotonin receptor agonist; Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	CA: Schedule I UK: Class B
Pharmacokinetic data
Duration of action	10–14 hours[1]
Identifiers
IUPAC name 1-[(4-ethoxy-2,5-dimethoxy)phenyl]propan-2-amine
CAS Number	16128-88-4 Y
PubChem CID	542053
ChemSpider	472023 Y
UNII	3I0ORO8174
ChEMBL	ChEMBL8225 Y
CompTox Dashboard (EPA)	DTXSID00337348
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1cc(OC)c(cc1OC)CC(N)C)CC
InChI InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 Y Key:ITZLAXJQDMGDEO-UHFFFAOYSA-N Y
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Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MEM's dose as 20 to 50 mg orally and its duration as 10 to 14 hours.^[1][3] Its effects have been reported to include color enhancement, visual phenomena, and pattern movement, among others.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

MEM activities

Target	Affinity (Ki, nM)
5-HT1A	>10,000
5-HT1B	>10,000
5-HT1D	>10,000
5-HT1E	>10,000
5-HT1F	ND
5-HT2A	73.0–3,948 (Ki) 47.5–295 (EC50Tooltip half-maximal effective concentration) 88–105% (EmaxTooltip maximal efficacy)
5-HT2B	64.5–763 (Ki) 437–557 (EC50) 70–96% (Emax)
5-HT2C	124–>10,000 (Ki) 29.9–248 (EC50) 98–129% (Emax)
5-HT3	>10,000
5-HT4	ND
5-HT5A	>10,000
5-HT6	>10,000
5-HT7	7,156
α1A, α1B	>10,000
α1D	ND
α2A–α2C	>10,000
β1, β2	>10,000
β3	ND
D1–D5	>10,000
H1–H4	>10,000
M1–M5	>10,000
I1	>10,000
σ1	5,077
σ2	>10,000
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	>10,000 (Ki)
NETTooltip Norepinephrine transporter	>10,000 (Ki)
DATTooltip Dopamine transporter	>10,000 (Ki)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [4][5][6][7][8][9][10]

MEM is a serotonergic psychedelic and acts as a selective serotonin 5-HT₂ receptor agonist.^{[6][7][8][9][10]} It is specifically a full agonist of the serotonin 5-HT_2A and 5-HT_2C receptors and to a lesser extent is a partial to full agonist of the serotonin 5-HT_2B receptor.^[6][7][9] The psychedelic effects of MEM are thought to be mediated by serotonin 5-HT_2A receptor activation.^[7]

Chemistry

MEM, also known as 2,5-dimethoxy-4-ethoxyamphetamine, is a phenethylamine, amphetamine, and DOx derivative. It is the analogue and derivative of 2,4,5-trimethoxyamphetamine (TMA-2) in which a 4-ethoxy group is present instead of a 4-methoxy group.

Synthesis

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

Derivatives

A variety of derivatives of MEM have been developed and studied, for instance by Daniel Trachsel and colleagues.^[11][12] These include MPM, MIPM, MALM, MMALM, MFEM, MDFEM, and MTFEM, among others.^[11][12]

History

MEM was first synthesized by Alexander Shulgin.^[1][2] It was first described by him in the scientific literature by 1968.^[2] Subsequently, Shulgin described MEM in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

See also

• 2,5-Dimethoxy-4-substituted amphetamines (DOx)