4-MeO-DMT

4-MeO-DMT, or 4-methoxy-DMT, also known as 4-methoxy-N,N-dimethyltryptamine or as O-methylpsilocin (PSOM), is a serotonin receptor modulator and possible psychedelic drug of the tryptamine and 4-hydroxytryptamine families.^{[1][2][3][4][5]} It is the O-methylated analogue of psilocin (4-HO-DMT) and a positional isomer of 5-MeO-DMT.^[1][5]

4-MeO-DMT

Clinical data
Other names	4-OMe-DMT; 4-Methoxy-DMT; 4-Methoxy-N,N-dimethyltryptamine; O-Methylpsilocin; PSOM
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 2-(4-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	3965-97-7 Y
PubChem CID	12017578
ChemSpider	23126449 Y
UNII	X4NBI2F334
ChEMBL	ChEMBL32029 Y
CompTox Dashboard (EPA)	DTXSID20475892
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.300 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1=CNC2=CC=CC(OC)=C21
InChI InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3 Y Key:HFYHBTWTJDAYGW-UHFFFAOYSA-N Y
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Use and effects

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 4-MeO-DMT is not known to have been tested in humans.^[6] However, the N,N-diethyl analogue 4-MeO-DET has been tested in humans and was found to be completely inactive at doses of up to 30 mg orally or smoked.^[6]

Interactions

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

Pharmacology

Pharmacodynamics

4-MeO-DMT activities

Target	Affinity (Ki, nM)
5-HT1A	235
5-HT2A	68–1,300
5-HT2C	340
Notes: The smaller the value, the more avidly the drug interacts with the site. Sources:[7][8]

4-MeO-DMT has shown high affinity for several serotonin receptors, including the serotonin 5-HT_1A receptor (K_i = 235 nM), the serotonin 5-HT_2A receptor (K_i = 68–1,300 nM), and the serotonin 5-HT_2C receptor (K_i = 340 nM).^[7][8] Compared to 5-MeO-DMT, 4-MeO-DMT had similar affinity for the serotonin 5-HT_2A receptor, but showed much lower affinity (21-fold) for the serotonin 5-HT_1A receptor.^[7][8] The drug shows pronounced biased agonism at the serotonin 5-HT_2C receptor.^[9]

4-MeO-DMT produces serotonergic psychedelic-like effects in animals, including rodents and monkeys.^{[1][2][3][4][5]} It has been found to disrupt object size discrimination performance in monkeys, suggesting that it may have psychedelic effects in humans.^[1][10] However, whereas 5-MeO-DMT has greater potency than bufotenin (5-HO-DMT), 4-MeO-DMT has lower potency than psilocybin (4-PO-DMT).^[1] This may be due to the fact that the lipophilicity of psilocin is not importantly enhanced by O-methylation, in contrast to the case of bufotenin, which has associated limitations in terms of blood–brain barrier permeability.^[1] Besides psilocin/psilocybin, 4-MeO-DMT is also less potent than 5-MeO-DMT.^[2]

4-MeO-DMT fully substituted for DOM in rodent drug discrimination tests, with an ED₅₀Tooltip median effective dose of about 3.53 mg/kg and about 3-fold lower potency than 5-MeO-DMT.^[11] 4-MeO-DMT also substituted for 5-MeO-DMT in rodent drug discrimination tests, with an ED₅₀ of 3.47 μmol/kg and about 2.7-fold lower potency than 5-MeO-DMT.^[12]

Chemistry

Analogues

Analogues of 4-MeO-DMT include dimethyltryptamine (DMT), 4-methoxytryptamine (4-MT or 4-MeO-T), psilocin (4-HO-DMT), 4-AcO-DMT (psilacetin), 4-MeO-DET, 4-MeO-DiPT, 4-MeO-MiPT, 5-MeO-DMT, 6-MeO-DMT, and 7-MeO-DMT, among others.^[6]

History

4-MeO-DMT was first described in the scientific literature by at least 1968.^[1][13]

Society and culture

Legal status

In the United States 4-MeO-DMT is a Schedule 1 controlled substance as it is a positional isomer of 5-MeO-DMT.^[14]

See also

• Substituted tryptamine