2-TOET

2-TOET, also known as 2-methylthio-4-ethyl-5-methoxyamphetamine or as 2-thio-DOET, is a psychoactive drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOET.^[1][2][3][4] It is the analogue of DOET in which the methoxy group at the 2 position has been replaced with a methylthio group.^[1][2][3][4] The drug is one of two possible TOET (thio-DOET) positional isomers, the other being 5-TOET.^[1][2][3][4]

Other names2-Methylthio-4-ethyl-5-methoxyamphetamine; 4-Ethyl-2-methylthio-5-methoxyamphetamine; 2-Thio-DOET; 2T-DOET; 2-Methylthio-DOET

Routes of
administrationOral^[1]

Drug classPsychoactive drug

ATC code

• None

Quick facts Clinical data, Other names ...

2-TOET

Clinical data
Other names	2-Methylthio-4-ethyl-5-methoxyamphetamine; 4-Ethyl-2-methylthio-5-methoxyamphetamine; 2-Thio-DOET; 2T-DOET; 2-Methylthio-DOET
Routes of administration	Oral[1]
Drug class	Psychoactive drug
ATC code	None
Pharmacokinetic data
Duration of action	Unknown (but long-lasting)[1]
Identifiers
IUPAC name 1-(4-ethyl-5-methoxy-2-methylsulfanylphenyl)propan-2-amine
CAS Number	779279-63-9
PubChem CID	15915347
ChemSpider	21106408
UNII	28GRS3DSL2
Chemical and physical data
Formula	C13H21NOS
Molar mass	239.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC1=CC(=C(C=C1OC)CC(C)N)SC
InChI InChI=1S/C13H21NOS/c1-5-10-8-13(16-4)11(6-9(2)14)7-12(10)15-3/h7-9H,5-6,14H2,1-4H3 Key:TZIBUOSWJBKVTA-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOET's dose as greater than 65 mg orally and its duration as unknown (but long-lasting).^[1][2][4] The drug is more than 10-fold less potent than DOET, which has a listed dose range of 2 to 6 mg orally.^[1][2][3]

The effects of 2-TOET have been reported to include slight lightheadedness, feeling physically a bit fragile, possible appetite loss, possible erectile dysfunction, and next-day residual fragility.^[1] It was described as inactive as a hallucinogen at assessed doses, and higher doses were not tested.^[1][2]

The chemical synthesis of 2-TOET has been described.^[1][4] The phenethylamine analogue, 2C-2-TOET (2-thio-2C-E), has been synthesized, but was not tested and its properties are unknown.^[1]

2-TOET was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983.^[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]