4-MeO-DMT

4-MeO-DMT (4-methoxy-N,N-dimethyltryptamine) is a tryptamine derivative which has some central activity in animal tests similar to that of related psychedelic tryptamine drugs, although with significantly lower potency than either 5-MeO-DMT or 4-hydroxy-DMT (psilocin).^[1]^[2]^[3]^[4]

Quick Facts Identifiers, CAS Number ...

4-MeO-DMT
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
^NY (what is this?) (verify)

References

[1]
Glennon RA, Young R, Benington F, Morin RD (February 1982). "Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts". Life Sciences. 30 (5): 465–7. doi:10.1016/0024-3205(82)90463-5. PMID 6801410.
[2]
Kline TB, Benington F, Morin RD, Beaton JM (August 1982). "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry. 25 (8): 908–13. doi:10.1021/jm00350a005. PMID 7120280.
[3]
Kline TB, Benington F, Morin RD, Beaton JM, Glennon RA, Domelsmith LN, Houk KN, Rozeboom MD (November 1982). "Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives". Journal of Medicinal Chemistry. 25 (11): 1381–3. doi:10.1021/jm00353a021. PMID 6815326.
[4]
Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. pp. 95–142.
[5]
"Lists of Scheduling Actions Controlled Substances Regulated Chemical" (PDF). deadiversion.usdoj.gov. Retrieved 8 April 2023.

4-MeO-DMT


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
^NY (what is this?) (verify)

[1]
Glennon RA, Young R, Benington F, Morin RD (February 1982). "Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts". Life Sciences. 30 (5): 465–7. doi:10.1016/0024-3205(82)90463-5. PMID 6801410.
[2]
Kline TB, Benington F, Morin RD, Beaton JM (August 1982). "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry. 25 (8): 908–13. doi:10.1021/jm00350a005. PMID 7120280.
[3]
Kline TB, Benington F, Morin RD, Beaton JM, Glennon RA, Domelsmith LN, Houk KN, Rozeboom MD (November 1982). "Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives". Journal of Medicinal Chemistry. 25 (11): 1381–3. doi:10.1021/jm00353a021. PMID 6815326.
[4]
Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. pp. 95–142.
[5]
"Lists of Scheduling Actions Controlled Substances Regulated Chemical" (PDF). deadiversion.usdoj.gov. Retrieved 8 April 2023.

Legality