5-MeO-NBnT

5-MeO-NBnT
Clinical data
Other names5-MeO-T-NB; N-Benzyl-5-methoxytryptamine; 3-(2'-Benzylaminoethyl)-5-methoxyindol
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • N-benzyl-2-(5-methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H20N2O
Molar mass280.371 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2CCNCC3=CC=CC=C3
  • InChI=1S/C18H20N2O/c1-21-16-7-8-18-17(11-16)15(13-20-18)9-10-19-12-14-5-3-2-4-6-14/h2-8,11,13,19-20H,9-10,12H2,1H3
  • Key:FQRAHCLOFRBKKA-UHFFFAOYSA-N

5-MeO-NBnT, also known as N-benzyl-5-methoxytryptamine or as 5-MeO-T-NB, is a serotonin receptor agonist of the tryptamine and 5-methoxytryptamine families related to 5-MeO-NMT.[1][2][3][4]

Pharmacology

Pharmacodynamics

5-MeO-NBnT binds to the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors (Ki = 5.3–55 nM, 16.6 nM, and 95.5–370 nM, respectively).[2][4] It was assessed and found to be a potent partial agonist of the serotonin 5-HT2A receptor (EC50Tooltip half-maximal effective concentration = 20.4–100 nM; EmaxTooltip maximal efficacy = 30–63%) and full agonist of the serotonin 5-HT2C receptor (EC50 = 14.5 nM; Emax = 113%).[3][5][6][4] The drug was not evaluated in terms of effects in animals.[2][3][4]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-NBnT has been described.[3]

Analogues

Analogues of 5-MeO-NBnT include N-benzyltryptamine (NBnT), 4-HO-NBnT, 5-MeO-NBOMeT, and 5-MeO-NB3OMeT, among others. It is also analogous to N-benzylphenethylamines, for instance 25-NB (NBOMe), 25B-NB (N-benzyl-2C-B), and 25I-NBOMe.

History

5-MeO-NBnT was first described in the scientific literature by Keijiro Takagi and colleagues by 1969.[1]

See also

References

  1. ^ a b Takagi K, Takayanagi I, Irikura T, Nishino K, Ito M (June 1969). "A potent competitive inhibitor of 5-hydroxytryptamine: 3-(2'-benzylaminoethyl)-5-methoxyindol hydrochloride". Japanese Journal of Pharmacology. 19 (2): 234–239. doi:10.1254/jjp.19.234. PMID 5308828.
  2. ^ a b c Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–1935. doi:10.1021/jm00039a004. PMID 8027974.
  3. ^ a b c d Heim R (2003). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Thesis) (in German). Berlin: Freie Univ. Tab. 3-10. 5-HT2A-Rezeptoraktivität der N-Benzyl-2-(1H-indol-3-yl)ethylamin-Derivate 199 – 207, untersucht an 5-HT2ARezeptoren der isolierten Rattenschwanzarterie [...] [Compound:] 204 [...]
  4. ^ a b c d Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK (2019). "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE. 14 (1) e0209804. Bibcode:2019PLoSO..1409804T. doi:10.1371/journal.pone.0209804. PMC 6328172. PMID 30629611.
  5. ^ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD.). Universität Regensburg. Table 5.1: Agonistic potency (pEC50) and intrinsic activity (Emax) of 5-HT2AR partial agonistic arylethylamines (indole, methoxybenzene and quinazolinedione derivatives) used in the study. [...] [Compound] 204 [...]
  6. ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
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