25F-NBOMe

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;

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 activities
Target	Affinity (K_i, nM)
5-HT_1A	ND
5-HT_1B	6,331
5-HT_1D	5,052
5-HT_1E	ND
5-HT_1F	ND
5-HT_2A	3.3 (K_i) 16 (EC₅₀Tooltip half-maximal effective concentration) 75% (E_maxTooltip maximal efficacy)
5-HT_2B	7.5 (K_i) ND (EC₅₀) ND (E_max)
5-HT_2C	43 (K_i) (rat) 25 (EC₅₀) 92% (E_max)
5-HT₃	ND
5-HT₄	ND
5-HT_5A	ND
5-HT₆	80
5-HT₇	ND
α_1A–α_1D	ND
α_2A–α_2C	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 (K_i) ND (IC₅₀Tooltip half-maximal inhibitory concentration) ND (EC₅₀)
NETTooltip Norepinephrine transporter	ND (K_i) ND (IC₅₀) ND (EC₅₀)
DATTooltip Dopamine transporter	ND (K_i) 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: ^[1]^[2]

Pharmacology

Pharmacodynamics

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]

References

^ ^a ^b ^c ^d ^e Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
^ ^a ^b ^c ^d ^e Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.

External links

[Hansen_2010-1] Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.

[Hansen_2014-2] Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.

[1]

[2]