5-MeO-2-TMT

5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT, 5-MeO-TMT), also known as 2-methyl-5-methoxy-N,N-dimethyltryptamine (2-Me-5-MeO-DMT), is a serotonin receptor modulator and psychedelic drug of the tryptamine and 2-alkyltryptamine families.^{[1][3][4][2][5]} It was first synthesized by Alexander Shulgin and reported in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).^[1]

5-MeO-2-TMT

Clinical data
Other names	5-Methoxy-2,N,N-trimethyltryptamine; 5-MeO-2,N,N-TMT; 5-MeO-TMT; 2-Methyl-5-methoxy-N,N-dimethyltryptamine; 2-Me-5-MeO-DMT; Indapex; MMDT; 5-Methoxy-2-methyl-DMT
Routes of administration	Oral[1][2]
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A
Pharmacokinetic data
Duration of action	5–10 hours[1][2]
Identifiers
IUPAC name 2-(5-methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	67292-68-6
PubChem CID	49756
ChemSpider	45143 Y
UNII	XZ2CCP18I2
ChEMBL	ChEMBL7143 Y
CompTox Dashboard (EPA)	DTXSID10217627
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=C(N1)C=CC(=C2)OC)CCN(C)C
InChI InChI=1S/C14H20N2O/c1-10-12(7-8-16(2)3)13-9-11(17-4)5-6-14(13)15-10/h5-6,9,15H,7-8H2,1-4H3 Y Key:ACEHBQPPDDGCGZ-UHFFFAOYSA-N Y
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Dosage and effects

According to Alexander Shulgin in TiHKAL, 5-MeO-TMT has a dose range of 75 to 150 mg orally and a duration of 5 to 10 hours.^[1] It produces effects including sexual stimulation, enhanced orgasm, relaxation, sedation, tingling, sleep disturbances, chills and cold sensations, time dilation, reduced heart rate, reduced respiratory rate, mild nausea, motor incoordination, visual waviness, mild to pronounced closed-eye visuals, emotional lability, crying, body temperature fluctuations, uncomfortableness, gastrointestinal disturbances, and abdominal pain.^[1] It has been said that 5-MeO-TMT at a dose of 150 mg is definitely hallucinogenic and can be compared to a moderate 300 mg dose of mescaline.^[1]

Pharmacology

5-MeO-2-TMT activities

Target	Affinity (Ki, nM)
5-HT1A	200
5-HT1B	>10,000
5-HT1D	250
5-HT1E	1,800
5-HT1F	ND
5-HT2A	>10,000 (rat)
5-HT2B	ND
5-HT2C	4,020 (rat)
5-HT3	ND
5-HT4	ND
5-HT5A	10,450
5-HT6	60–80
5-HT7	145
α1A–α2C	ND
β1–β3	ND
D1–D5	>10,000
H1	>10,000
H2	ND
H3, H4	>10,000
M1–M5	>10,000
I1	ND
σ1, σ2	ND
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	>10,000
NETTooltip Norepinephrine transporter	6,380
DATTooltip Dopamine transporter	>10,000
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][3][5]

The affinities of 5-MeO-TMT for numerous targets have been reported.^[3][5] 2-Methyltryptamines like 5-MeO-TMT show a loss of affinity for the serotonin 5-HT_2A receptor but retained affinity for the serotonin 5-HT₆ receptor.^[4][5][3] It also retains significant affinity for the serotonin 5-HT_1A, 5-HT_1D, and 5-HT₇ receptors.^[3][5] In contrast to 5-MeO-DMT, 5-MeO-TMT is orally active, suggesting that the 2-methyl group blocks metabolism by monoamine oxidase (MAO).^[1]

See also

• 2-Methyltryptamine (2-MT or 2-Me-T)
• 2-Methyl-N,N-diethyltryptamine (2-Me-DET)
• 2,N,N-Trimethyltryptamine (2,N,N-TMT or 2-Me-DMT)
• 2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT)
• 5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7-TMT or 7-Me-5-MeO-DMT)
• 2-Ethyl-5-methoxy-N,N-dimethyltryptamine (EMDT; 2-Et-5-MeO-DMT)
• BGC20-761 (5-MeO-2-phenyl-DMT)