5-Thiometaescaline

5-Thiometaescaline (5-TME), also known as 3-ethoxy-4-methoxy-5-methylthiophenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline.^[1][2][3] It is the analogue of metaescaline in which the methoxy group at the 5 position has been replaced with a methylthio group.^[1][2][3] The drug is one of three possible positional isomers of thiometaescaline (TME), the others being 3-thiometaescaline (3-TME) and 4-thiometaescaline (4-TME).^[1][2][3]

Other names5-TME; 3-Ethoxy-4-methoxy-5-methylthiophenethylamine; 3-EtO-4-MeO-5-MeS-PEA

Routes of
administrationOral^[1]

ATC code

• None

Duration of actionUnknown^[1]

Quick facts Clinical data, Other names ...

5-Thiometaescaline

Clinical data
Other names	5-TME; 3-Ethoxy-4-methoxy-5-methylthiophenethylamine; 3-EtO-4-MeO-5-MeS-PEA
Routes of administration	Oral[1]
ATC code	None
Pharmacokinetic data
Duration of action	Unknown[1]
Identifiers
IUPAC name 2-(3-ethoxy-4-methoxy-5-methylsulfanylphenyl)ethanamine
CAS Number	90132-39-1
PubChem CID	44374913
ChemSpider	21106385
UNII	FSA7T3D9DJ
ChEMBL	ChEMBL160106
Chemical and physical data
Formula	C12H19NO2S
Molar mass	241.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC1=C(C(=CC(=C1)CCN)SC)OC
InChI InChI=1S/C12H19NO2S/c1-4-15-10-7-9(5-6-13)8-11(16-3)12(10)14-2/h7-8H,4-6,13H2,1-3H3 Key:BRABKKMYSDDDCR-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 5-TME's dose as greater than 200 mg orally and its duration as unknown.^[1][2] The effects of 5-TME have been reported to include possible tinnitus, a possible brush of lightheadedness, and nothing else, but these changes could not be clearly ascribed to the drug.^[1]

The chemical synthesis of 5-TME has been described.^[1][3]

5-TME was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984.^[3] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]