3-Thiosymbescaline

3-Thiosymbescaline (3-TSB), also known as 3-ethylthio-4-methoxy-5-ethoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline.^[1][2][3][4] It is the analogue of symbescaline in which the ethoxy group at the 3 position has been replaced with an ethylthio group.^[1][2][3][4] The compound is one of two possible thiosymbescaline (TSB) positional isomers, the other being 4-thiosymbescaline (4-TSB).^[1][2][3][4]

Other names3-TSB; 3-Ethylthio-4-methoxy-5-ethoxyphenethylamine; 3-EtS-4-MeO-5-EtO-PEA

Routes of
administrationOral^[1]

ATC code

• None

Duration of actionUnknown^[1]

Quick facts Clinical data, Other names ...

3-Thiosymbescaline

Clinical data
Other names	3-TSB; 3-Ethylthio-4-methoxy-5-ethoxyphenethylamine; 3-EtS-4-MeO-5-EtO-PEA
Routes of administration	Oral[1]
ATC code	None
Pharmacokinetic data
Duration of action	Unknown[1]
Identifiers
IUPAC name 2-(3-ethoxy-5-ethylsulfanyl-4-methoxyphenyl)ethanamine
CAS Number	90132-51-7
PubChem CID	44374939
ChemSpider	21106412
UNII	28S8H9WR9W
ChEMBL	ChEMBL349363
Chemical and physical data
Formula	C13H21NO2S
Molar mass	255.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC1=C(C(=CC(=C1)CCN)SCC)OC
InChI InChI=1S/C13H21NO2S/c1-4-16-11-8-10(6-7-14)9-12(17-5-2)13(11)15-3/h8-9H,4-7,14H2,1-3H3 Key:BTJFGKUKBHSKHI-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-TSB's dose as greater than 200 mg orally and its duration as unknown.^[1][2][3] The compound produced no effects whatsoever at a dose of up to 200 mg orally.^[1]

The chemical synthesis of 3-TSB has been described.^[1][4]

3-TSB was first described in the scientific literature by Shulgin and Peyton Jacob III in 1984.^[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]