2C-T-22

2C-T-22, also known as 4-(2,2,2-trifluoroethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine, 2C, and 2C-T-x families.^[1][2] It is closely related to 2C-T-21 (the 4-(2-fluoroethylthio) analogue and 2C-T-21.5 (the 4-(2,2-difluoroethylthio) analogue).^[1][2]

2C-T-22

Clinical data
Other names	4-(2,2,2-Trifluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2,2,2-trifluoroethylthio)phenethylamine
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	~6 hours[1]
Identifiers
IUPAC name 2-[2,5-dimethoxy-4-(2,2,2-trifluoroethylsulfanyl)phenyl]ethanamine
CAS Number	648957-48-6
PubChem CID	12063259
Chemical and physical data
Formula	C12H16F3NO2S
Molar mass	295.32 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1CCN)OC)SCC(F)(F)F
InChI InChI=1S/C12H16F3NO2S/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3 Key:LDOOFVKAIHFXAR-UHFFFAOYSA-N

The drug was briefly described by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in the 2C-T-21 entry, but Shulgin only partially completed the chemical synthesis of 2C-T-22 and did not test it.^[2] Subsequently, Daniel Trachsel completed the synthesis of 2C-T-22 and defined its dose as greater than 10 mg orally and its duration as approximately 6 hours.^[1] A total dose of 5 mg plus 5 mg plus 6 mg produced the first signs of effects, but higher doses were not explored.^[1][3] Hence, its precise dose range remains unknown.^[4][1][3]

2C-T-22 shows affinity for the serotonin 5-HT_2A receptor (K_i = 16–102 nM) and the serotonin 5-HT_2C receptor (K_i = 28–151 nM).^[1][5] It has been found to be a potent partial agonist of the serotonin 5-HT_2A and 5-HT_2B receptors.^[5] Other receptor and target interactions have also been described.^[5]

2C-T-22 was first described in the scientific literature by Shulgin in his book PiHKAL in 1991.^[2] Subsequently, Trachsel described and completed the synthesis of 2C-T-22 in 2003^[6] and he and his colleagues defined its properties in humans in 2013.^[1][3]

See also

• 2C (psychedelics)