5-TOET

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

Other names2-Methoxy-4-ethyl-5-methylthioamphetamine; 4-Ethyl-2-methoxy-5-methylthioamphetamine; 5-Thio-DOET; 5T-DOET; 5-Methylthio-DOET

Routes of
administrationOral^[1]

Drug classSerotonergic psychedelic; Hallucinogen

ATC code

• None

Quick facts Clinical data, Other names ...

5-TOET

Clinical data
Other names	2-Methoxy-4-ethyl-5-methylthioamphetamine; 4-Ethyl-2-methoxy-5-methylthioamphetamine; 5-Thio-DOET; 5T-DOET; 5-Methylthio-DOET
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Onset of action	30 minutes[2] Peak: 4 hours[2]
Duration of action	8–24 hours[1]
Identifiers
IUPAC name 1-(4-ethyl-2-methoxy-5-methylsulfanylphenyl)propan-2-amine
CAS Number	207740-43-0
PubChem CID	15915351
ChemSpider	21106386
UNII	53KPR8B3A4
ChEMBL	ChEMBL127095
Chemical and physical data
Formula	C13H21NOS
Molar mass	239.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC1=CC(=C(C=C1SC)CC(C)N)OC
InChI InChI=1S/C13H21NOS/c1-5-10-7-12(15-3)11(6-9(2)14)8-13(10)16-4/h7-9H,5-6,14H2,1-4H3 Key:CBSUPAQTEZIWSK-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 5-TOET's dose as 12 to 25 mg orally and its duration as 8 to 24 hours.^[1][3][2] Its onset is about 30 minutes and its time to peak is about 4 hours.^[2] The drug is around 5-fold less potent than DOET, which has a listed dose range of 2 to 6 mg orally.^[1][4]

The effects of 5-TOET have been reported to include closed-eye imagery and fantasy, open-eye visuals such as brightness around objects and visual movement, feelings of joy, beauty, love, and serenity, erotic enhancement, restlessness, lightheadedness, pupil dilation, sleep disturbances, and next-day afterglow as well as lethargy.^[1][2] One user described it as "superb", "exquisite", and potentially "extraordinary".^[1] It has much less physical discomfort than 5-TOM.^[1][2] There also appears to be significant interindividual variability in intensity of 5-TOET, with two of eight people being roughly twice as sensitive as the others.^[1][2] In addition, an unintentional overdose in one person, despite a similar dose taken as others, was described as intense, exhausting, and too long-lived.^[1]

The chemical synthesis of 5-TOET has been described.^[1][2] The phenethylamine analogue, 2C-5-TOET (5-thio-2C-E), has been synthesized, but was not tested and its properties are unknown.^[1]

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