24H-NBF

24H-NBF
Clinical data
Drug class	Serotonin receptor modulator; 5-HT2A receptor agonist; putative psychedelic (hallucinogenic drug)
ATC code	none;
Identifiers
	IUPAC name 2-(2,4-Dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethan-1-amine;
Chemical and physical data
3D model (JSmol)	Interactive image;
	SMILES COc1cc(OC)ccc1CCNCc1ccccc1F;
	InChI InChI=InChI=1S/C17H20FNO2/c1-20-15-8-7-13(17(11-15)21-2)9-10-19-12-14-5-3-4-6-16(14)18/h3-8,11,19H,9-10,12H2,1-2H3; Key:JQZYDEUAIHIHLI-UHFFFAOYSA-N;

24H-NBF also known as N-(2-fluorobenzyl)-2,4-dimethoxyphenethylamine (2,4-DMPEA-NBF) is a serotonin receptor modulator and a putative psychedelic from the 24-NB family; it is an N-(2-fluorobenzyl) derivative of 2,4-dimethoxyphenethylamine and is a positional isomer of many other compounds in the "NBF" class (which are N-benzyl derivatives of other methoxyphenethylamines with a fluorine substituent at the 2-position of the carbon in the N-benzyl moiety; amongst these (including compounds such as 25H-NBF), it is the most potent in terms of efficacy and binding to the serotonin 5-HT_2A receptor).^[1]^[2]

Pharmacology

Pharmacodynamics

24H-NBF is a full agonist (E_max was 106–107 per cent) of the serotonin 5-HT_2A receptor, with an EC₅₀ of 158 nM; this was measured by assessing the extent to which the receptor binds the β-arrestin 2 protein.^[1]^[2]

It was known that 24H-NBF had an anxiolytic effect, suppressing emotions and motor activity in vivo.^[3]

References

1 2 Pottie, Eline; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Stove, Christophe P. (2021-04-28). "Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers". ACS Chemical Neuroscience. 12 (9): 1667–1673. doi:10.1021/acschemneuro.1c00124. ISSN 1948-7193.
1 2 Kupriyanova, Olga V.; Shevyrin, Vadim A.; Shafran, Yuri M. "Potential of chromatography and mass spectrometry for the differentiation of three series of positional isomers of 2‐(dimethoxyphenyl)‐ N ‐(2‐halogenobenzyl)ethanamines". Drug Testing and Analysis. 14 (6): 1102–1115. doi:10.1002/dta.3232. ISSN 1942-7603.
↑ Demin, Konstantin A.; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Derzhavina, Ksenia A.; Krotova, Nataliya A.; Ilyin, Nikita P.; Kolesnikova, Tatiana O.; Galstyan, David S.; Kositsyn, Yurii M.; Khaybaev, Abubakar-Askhab S.; Seredinskaya, Maria V.; Dubrovskii, Yaroslav; Sadykova, Raziya G.; Nerush, Maria O.; Mor, Mikael S. (2022-07-06). "Acute behavioral and Neurochemical Effects of Novel N-Benzyl-2-Phenylethylamine Derivatives in Adult Zebrafish". ACS chemical neuroscience. 13 (13): 1902–1922. doi:10.1021/acschemneuro.2c00123. ISSN 1948-7193. PMID 35671176.

[:0-1] 1 2 Pottie, Eline; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Stove, Christophe P. (2021-04-28). "Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers". ACS Chemical Neuroscience. 12 (9): 1667–1673. doi:10.1021/acschemneuro.1c00124. ISSN 1948-7193.

[:1-2] 1 2 Kupriyanova, Olga V.; Shevyrin, Vadim A.; Shafran, Yuri M. "Potential of chromatography and mass spectrometry for the differentiation of three series of positional isomers of 2‐(dimethoxyphenyl)‐ N ‐(2‐halogenobenzyl)ethanamines". Drug Testing and Analysis. 14 (6): 1102–1115. doi:10.1002/dta.3232. ISSN 1942-7603.

[3] Demin, Konstantin A.; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Derzhavina, Ksenia A.; Krotova, Nataliya A.; Ilyin, Nikita P.; Kolesnikova, Tatiana O.; Galstyan, David S.; Kositsyn, Yurii M.; Khaybaev, Abubakar-Askhab S.; Seredinskaya, Maria V.; Dubrovskii, Yaroslav; Sadykova, Raziya G.; Nerush, Maria O.; Mor, Mikael S. (2022-07-06). "Acute behavioral and Neurochemical Effects of Novel N-Benzyl-2-Phenylethylamine Derivatives in Adult Zebrafish". ACS chemical neuroscience. 13 (13): 1902–1922. doi:10.1021/acschemneuro.2c00123. ISSN 1948-7193. PMID 35671176.

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