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2C-B-morpholine

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Pharmaceutical compound
2C-B-morpholine
Clinical data
Other names2C-B-Norphenmetrazine; 2-(4-Bromo-2,5-dimethoxyphenyl)morpholine
Drug classSerotonin receptor modulator;Serotonin5-HT2A receptorligand
ATC code
  • None
Identifiers
  • 2-(4-bromo-2,5-dimethoxyphenyl)morpholine
CAS Number
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC12H16BrNO3
Molar mass302.168 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1C2CNCCO2)OC)Br
  • InChI=1S/C12H16BrNO3/c1-15-10-6-9(13)11(16-2)5-8(10)12-7-14-3-4-17-12/h5-6,12,14H,3-4,7H2,1-2H3
  • Key:OUTZYBJUJMETRJ-UHFFFAOYSA-N

2C-B-morpholine, also known as2C-B-norphenmetrazine or as2-(4-bromo-2,5-dimethoxyphenyl)morpholine, is aserotonin receptor modulator of thephenylmorpholine (phenmetrazine) andcyclized phenethylamine groups.[1] It is aligand of theserotonin5-HT2A receptor, with anaffinity of 20.6 nM and anEmaxTooltip maximal efficacy of 4%.[1] The drug showed 103-fold lower affinity for this receptor thanR(–)-DOB and had minimalagonist activity (withR(–)-DOB having anEmax of 51% in the assay), so for practical purposes would act as an antagonist at the 5-HT2A receptor under most circumstances, despite being technically classified as a partial agonist.[1] 2C-B-morpholine was first described in thescientific literature byRichard Glennon and colleagues by 2004.[1]

See also

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References

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  1. ^abcdGlennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, et al. (November 2004)."Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane".Journal of Medicinal Chemistry.47 (24):6034–6041.doi:10.1021/jm040082s.PMID 15537358.One of the first compounds prepared and examined in this investigation was morpholine analogue 2. Compound 2 bears an ether oxygen atom at the benzylic position that is tethered to the terminal amine. However, its 5-HT2A affinity (Ki) 20.6 nM) is 100-fold lower than that of R(-)DOB (Ki) 0.2 nM), and its agonist efficacy in the 5-HT2-mediated calcium mobilization assay is minimal (Table 1). There are several possible explanations for these unfavorable findings. Apart from the molecule possessing a chiral center, the ether oxygen atom might not be tolerated by the receptor and/or the added ethylene "bridge" might not be readily accommodated by the receptor and its presence detracts from affinity. A more plausible explanation, based on prior structure-affinity investigations, is that the secondary amine of 2 contributes to decreased affinity. That is, we have previously shown that addition of small N-alkyl substituents can reduce the 5-HT2A receptor affinity of DOB and DOB-related compounds.16,17

External links

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