2C-tBu

2C-tBu, or 2C-t-Bu, also known as 4-tert-butyl-2,5-dimethoxyphenethylamine, is a serotonin receptor agonist and putative serotonergic psychedelic of the phenethylamine and 2C families.^[1][2]

2C-tBu

Clinical data
Other names	2,5-Dimethoxy-4-tert-butylphenethylamine; 4-tert-Butyl-2,5-dimethoxyphenethylamine; 2C-TBU; 2C-t-Bu
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(4-tert-butyl-2,5-dimethoxyphenyl)ethanamine
PubChem CID	117347542
ChemSpider	76370331
Chemical and physical data
Formula	C14H23NO2
Molar mass	237.343 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)C1=C(C=C(C(=C1)OC)CCN)OC
InChI InChI=1S/C14H23NO2/c1-14(2,3)11-9-12(16-4)10(6-7-15)8-13(11)17-5/h8-9H,6-7,15H2,1-5H3 Key:MHNFTGKRRUDUST-UHFFFAOYSA-N

Use and effects

The active dose of 2C-tBu in humans is >5 mg orally per Daniel Trachsel and its duration is unknown.^[1] Initial tests with 7 mg and with 10 mg (as 5 mg plus 5 mg 2 hours apart) orally produced no psychedelic effects in humans, but instead induced a pronounced and long-lasting tiredness.^[1] It was hypothesized by Daniel Trachsel and colleagues that 2C-tBu might be a serotonin 5-HT_2A receptor antagonist and might thereby be hypnotic,^[1] but it was instead shown to be an agonist in subsequent studies.^[2]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

2C-tBu is a potent serotonin 5-HT_2A receptor agonist (K_i = 9.9–35 nM, EC₅₀Tooltip half-maximal effective concentration = 4.2 nM) and also binds to the serotonin 5-HT_2C receptor (K_i = 7–24 nM).^[1][2] The drug produces a robust head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[2] It also produces hyperlocomotion in rodents.^[2]

Chemistry

Analogues

Analogues of 2C-tBu include 2C-Bu, 2C-iBu, 2C-sBu, and DOTB, among others.^[1]

History

2C-tBu was first described in the scientific literature by Daniel Trachsel and colleagues in 2013.^[1]

See also

• 2C (psychedelics)