N-Methylcoclaurine

• CAT Number: R053739
• CAS Number: 5096-70-8
• Molecular Formula: C18H21NO3
• Molecular Weight: 299.37
• Purity: 95%
• Target: ĸ opioid receptor
• Storage: -20°C
• Related CAS: 57256-02-7
• IUPAC Name: (1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
• InChI: InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m1/s1
• InChIKey: BOKVLBSSPUTWLV-MRXNPFEDSA-N
• SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)O)OC

N-Methylcoclaurine(CAS 5096-70-8) is a kind of alkaloids extracted from Glaucium leiocarpum and other plants. N-Methylcoclaurine shows binding affinities for the ĸ opioid receptor with the equilibrium dissociation constant (Ki) value of 0.9 ± 0.1 uM. N-methylcoclaurine also shows promising butyrylcholinesterase inhibition activities, with the IC50 value of 15.0 ± 1.4 uM.

Reference

1. Nat Prod Commun. 2015 Apr;10(4):577-80.
Alkaloids from Peumus boldus and their acetylcholinesterase, butyrylcholinesterase and prolyl oligopeptidase inhibition activity.
Hošt'álková A, Opletal L, Kuneš J, Novák Z, Hrabinová M, Chlebek J, Čegan L, Cahlíková L.
Eleven isoquinoline alkaloids (1-11) were isolated from dried leaves of Peumus boldus Mol. by standard chromatographic methods. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analysis, and by comparison with literature data. Compounds isolated in sufficient amount were evaluated for their acetylcholinesterase, and butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro-p-nitroanilide was used as substrate. Promising butyrylcholinesterase inhibition activities were demonstrated by two benzylisoquinoline alkaloids, reticuline (8) and N-methylcoclaurine (9), with IC50 values of 33.6 ± 3.0 µM and 15.0 ± 1.4 µM, respectively. Important prolyl oligopeptidase inhibition activities were shown by N-methyllaurotetanine (6) and sinoacutine (4) with IC50 values of 135.4 ± 23.2 µM and 143.1 ± 25.4 µM, respectively. Other tested compounds were considered inactive.