25F-NBOMe

25F-NBOMe, also known as 2C-F-NBOMe or NBOMe-2C-F as well as N-(2-methoxybenzyl)-4-fluoro-2,5-dimethoxyphenethylamine, is a serotonin 5-HT₂ receptor agonist and possible serotonergic psychedelic of the phenethylamine, 2C, and 25-NB (NBOMe) families.^[1][2] It is the NBOMe (N-(2-methoxybenzyl)) derivative of 2C-F.^[1][2]

25F-NBOMe

Clinical data
Other names	2C-F-NBOMe; NBOMe-2C-F; N-(2-Methoxybenzyl)-4-fluoro-2,5-dimethoxyphenethylamine
Drug class	Serotonin 5-HT2 receptor agonist; Possible serotonergic psychedelic; Possible hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number	1373917-84-0 1539266-23-3 (hydrochloride)
PubChem CID	121230755
Chemical and physical data
Formula	C18H22FNO3
Molar mass	319.376 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)F)OC
InChI InChI=1S/C18H22FNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3 Key:DFTJMIFNIHIWAJ-UHFFFAOYSA-N

Pharmacology

Pharmacodynamics

25F-NBOMe activities

Target	Affinity (Ki, nM)
5-HT1A	ND
5-HT1B	6,331
5-HT1D	5,052
5-HT1E	ND
5-HT1F	ND
5-HT2A	3.3 (Ki) 16 (EC50Tooltip half-maximal effective concentration) 75% (EmaxTooltip maximal efficacy)
5-HT2B	7.5 (Ki) ND (EC50) ND (Emax)
5-HT2C	43 (Ki) (rat) 25 (EC50) 92% (Emax)
5-HT3	ND
5-HT4	ND
5-HT5A	ND
5-HT6	80
5-HT7	ND
α1A–α1D	ND
α2A–α2C	ND
β1–β3	ND
D1–D5	ND
H1–H4	ND
M1–M5	ND
I1	ND
σ1, σ2	ND
ORs	ND
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	ND (Ki) ND (IC50Tooltip half-maximal inhibitory concentration) ND (EC50)
NETTooltip Norepinephrine transporter	ND (Ki) ND (IC50) ND (EC50)
DATTooltip Dopamine transporter	ND (Ki) ND (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: [3][4]

25F-NBOMe acts as a potent agonist of the serotonin 5-HT_2A and 5-HT_2C receptors and also shows interactions with certain other targets, such as the serotonin 5-HT_2B receptor.^[1][2] However, it shows more than an order of magnitude lower potency as a serotonin 5-HT_2A receptor agonist than certain other NBOMe drugs like 25I-NBOMe and 25B-NBOMe in vitro.^[2]

History

25F-NBOMe was first described in the scientific literature by 2010.^[1]

See also

• 25-NB
• 2C-F
• DOF