α,N,N,O-TeMS

Clinical data
Other names	5-Methoxy-α-methyl-N,N-dimethyltryptamine; 5-Methoxy-α,N,N-trimethyltryptamine; α,N,N,O-Tetramethylserotonin; 5-MeO-α,N,N-TMT; 5-MeO-α-methyl-DMT; 5-MeO-α-Me-DMT; α,N,N,O-TeMS;N,N-Dimethyl-5-MeO-AMT
Identifiers
IUPAC name 1-(5-methoxy-1H-indol-3-yl)-N,N-dimethylpropan-2-amine
CAS Number	101831-90-7
PubChemCID	58946
ChemSpider	53134
CompTox Dashboard(EPA)	DTXSID90906668
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CNC2=C1C=C(C=C2)OC)N(C)C
InChI InChI=1S/C14H20N2O/c1-10(16(2)3)7-11-9-15-14-6-5-12(17-4)8-13(11)14/h5-6,8-10,15H,7H2,1-4H3 Key:WDKDEBAFCKHQPF-UHFFFAOYSA-N

α,N,N,O-Tetramethylserotonin (α,N,N,O-TeMS), also known as5-methoxy-α,N,N-trimethyltryptamine (5-MeO-α,N,N-TMT), is asyntheticcompound of thetryptamine,α-alkyltryptamine, and5-methoxytryptamine families.^[1][2][3] It is the combinedderivative ofα-methyltryptamine (αMT) and5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).^[1][2][3]

α,N,N,O-TeMS was described byAlexander Shulgin in his bookTiHKAL (Tryptamines I Have Known and Loved) as a putativepsychedelic drug.^[1] However, Shulgin does not appear to have eversynthesized orassayed it.^[1] As such, α,N,N,O-TeMS's effects,dose, andduration are all unknown.^[1]

α,N,N,O-TeMS is theN,N-dimethylated derivative of5-MeO-αMT (α,O-DMS) and theN-methylated derivative of5-MeO-α,N-DMT (α,N,O-TMS).^[1][2][3] 5-MeO-α,N-DMT is lesspotent and shorter in duration than 5-MeO-αMT, with 5-MeO-α,N-DMT having a dose range of 10 to 20 mg and a duration of 6 to 8 hours versus 5-MeO-αMT having a dose range of 2.5 to 4.5 mg and a duration of 12 to 18 hours.^[1][4] Similarly,α,N-DMT (α,N-dimethyltryptamine) is less potent than αMT, with doses of 50 to 100 mg for α,N-DMT and doses of 15 to 30 mg for αMT.^[4] Hence, of potential relevance to α,N,N,O-TeMS, it appears thatN-methylation of α-alkyltryptamines may reduce their activity by several-fold.^[1][4]

Analogues of α,N,N,O-TeMS (N,N-dimethyl-5-MeO-AMT) includeα-methyltryptamine (AMT),α,N-DMT (N-methyl-AMT),α,N,N-TMT (N,N-dimethyl-AMT),α-methylserotonin (5-HO-AMT),5-MeO-AMT (α,O-DMS), andα,N,O-TMS (N-methyl-5-MeO-AMT), among others.^[1] Another compound,zalsupindole ((R)-N,N-dimethyl-5-MeO-isoAMT), is a closeisotryptamine analogue of α,N,N,O-TeMS.^[5]

α,N,N,O-TeMS was first described in the literature, specifically inTiHKAL, by 1997.^[1] It is known to have been made atEdgewood Arsenal, but the facility never published anything on the compound.^[2] α,N,N,O-TeMS does not appear to have been otherwise described in the literature.^[2][3]

• Substituted α-alkyltryptamine

• 5-MeO-α-methyl-DMT - Isomer Design

• Alpha-Alkyltryptamines
• N,N-Dialkyltryptamines
• Dimethylamino compounds
• 5-Methoxytryptamines

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