2C-T-27

2C-T-27, also known as 4-benzylthio-2,5-dimethoxyphenethylamine, is a serotonin 5-HT_2A receptor agonist and serotonergic psychedelic of the phenethylamine and 2C families.^[1][2][3][4] It was first synthesized and described by Daniel Trachsel in 2003.^[2][3]

2C-T-27

Clinical data
Other names	4-Benzylthio-2,5-dimethoxyphenethylamine
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 2-(4-benzylsulfanyl-2,5-dimethoxyphenyl)ethanamine
PubChem CID	12063261
Chemical and physical data
Formula	C17H21NO2S
Molar mass	303.42 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1CCN)OC)SCC2=CC=CC=C2
InChI InChI=1S/C17H21NO2S/c1-19-15-11-17(16(20-2)10-14(15)8-9-18)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3 Key:GRZVJRPTNCONNT-UHFFFAOYSA-N

In addition to the serotonin 5-HT_2A receptor, 2C-T-27 interacts with the serotonin 5-HT_2C receptor.^[4] It showed higher affinity for the serotonin 5-HT_2A receptor than any other 2C drug (K_i = 1.6 nM), but its activational potency and efficacy were among the lowest (EC₅₀Tooltip half-maximal effective concentration = 26 nM; E_maxTooltip maximal efficacy = 27%).^[5][4]

The drug produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents.^[5] However, the HTR induced by 2C-T-27 is relatively weak.^[1]

2C-T-27 has been reported to produce hallucinogenic effects in humans.^[1] Its dosage was reported by Trachsel to be 80 mg or more orally and no duration was listed.^[1]

See also

• 2C-T-33
• 2C-T-8
• Aleph-6
• 3C-BZ
• Benzscaline (BZ)
• 2C-Ph