Α,N,N,O-TeMS

α,N,N,O-Tetramethylserotonin (α,N,N,O-TeMS), also known as 5-methoxy-α,N,N-trimethyltryptamine (5-MeO-α,N,N-TMT), is a little-known synthetic compound of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families.^[1][2][3] It is the combined derivative of α-methyltryptamine (αMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).^[1][2][3]

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
Identifiers
IUPAC name 1-(5-methoxy-1H-indol-3-yl)-N,N-dimethylpropan-2-amine
CAS Number	101831-90-7
PubChem CID	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

The drug was described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) as a putative psychedelic drug.^[1] However, Shulgin does not appear to have ever synthesized or assayed it.^[1] As such, α,N,N,O-TeMS's effects, dosage, and duration are all unknown.^[1]

α,N,N,O-TeMS is also the N,N-dimethylated derivative of 5-methoxy-α-methyltryptamine (5-MeO-αMT or α,O-DMS) and the N-methylated derivative of 5-methoxy-α,N-dimethyltryptamine (5-MeO-α,N-DMT or α,N,O-TMS).^[1][2][3] 5-MeO-α,N-DMT is less potent and long-lasting than 5-MeO-αMT, with 5-MeO-α,N-DMT having doses of 10 to 20 mg and a duration of 6 to 8 hours versus 5-MeO-αMT having doses of 2.5 to 4.5 mg and a duration of 12 to 18 hours.^[1][4] Similarly, α,N-dimethyltryptamine (α,N-DMT) 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, it appears that N-methylation of α-alkyltryptamines may reduce their activity and potency, by about 3- or 4-fold.^[1][4]

α,N,N,O-TeMS was first described in the literature, specifically in TiHKAL, by 1997.^[1] It is known to have been made at Edgewood 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]

See also

• α,N,N-Trimethyltryptamine (α,N,N-TMT)
• Zalsupindole ((R)-5-methoxy-α,N,N-trimethylisotryptamine; (R)-iso-5-MeO-α,N,N-TMT) – a close isotryptamine analogue of α,N,N,O-TeMS