25T4-NBOMe

25T4-NBOMe, also known as N-(2-methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine, is a serotonergic psychedelic of the 25-NB (NBOMe) family.^[2][3][4][5] It is the NBOMe analogue of 2C-T-4.^[2][3][4][5]

25T4-NBOMe

Clinical data
Other names	2C-T-4-NBOMe; NBOMe-2C-T-4; N-(2-Methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine
Routes of administration	Sublingual[1]
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(2,5-dimethoxy-4-propan-2-ylsulfanylphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number	1354632-17-9
PubChem CID	125181243
Chemical and physical data
Formula	C21H29NO3S
Molar mass	375.53 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)SC1=C(C=C(C(=C1)OC)CCNCC2=CC=CC=C2OC)OC
InChI InChI=1S/C21H29NO3S/c1-15(2)26-21-13-19(24-4)16(12-20(21)25-5)10-11-22-14-17-8-6-7-9-18(17)23-3/h6-9,12-13,15,22H,10-11,14H2,1-5H3 Key:BOWHVFJVXBVJCU-UHFFFAOYSA-N

Use and effects

25T4-NBOMe's reported active dose range has been described as 150 to 1,200 μg, with a typical dose estimate of 500 μg.^[1] The route is sublingual administration.^[1]

Interactions

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

Pharmacology

Pharmacodynamics

25T4-NBOMe activities

Target	Affinity (Ki, nM)
5-HT1A	2,500
5-HT1B	ND
5-HT1D	ND
5-HT1E	ND
5-HT1F	ND
5-HT2A	1.6 (Ki) 1.3–130 (EC50Tooltip half-maximal effective concentration) 46% (EmaxTooltip maximal efficacy)
5-HT2B	ND (Ki) 200 (EC50) 27% (Emax)
5-HT2C	16 (Ki) ND (EC50) ND (Emax)
5-HT3	ND
5-HT4	ND
5-HT5A	ND
5-HT6	ND
5-HT7	ND
α1A	580
α1B, α1D	ND
α2A	260
α2B, α2C	ND
β1–β3	ND
D1	4,900
D2	1,700
D3	1,900
D4, D5	ND
H1	5,400
H2–H4	ND
M1–M5	ND
I1	ND
σ1, σ2	ND
ORs	ND
TAAR1Tooltip Trace amine-associated receptor 1	1,500–1,600 (Ki) (mouse) 120 (Ki) (rat) 4,700 (EC50) (mouse) 1,100 (EC50) (rat) >10,000 (EC50) (human) 33% (Emax) (mouse) 31% (Emax) (rat)
SERTTooltip Serotonin transporter	8,100 (Ki) 14,000 (IC50Tooltip half-maximal inhibitory concentration) ND (EC50)
NETTooltip Norepinephrine transporter	4,300 (Ki) 28,000 (IC50) ND (EC50)
DATTooltip Dopamine transporter	6,200 (Ki) 58,000 (IC50) ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9]

25T4-NBOMe acts as a highly potent and selective agonist of the serotonin 5-HT₂ receptors.^[7][8] Its affinities and activities at a variety of other receptors and transporters have also been described.^[7]

History

25T4-NBOMe was first described in the scientific literature by at least 2012.^[10]

See also

• 25-NB
• 25T-NBOMe
• 25T2-NBOMe
• 25T7-NBOMe