Synephrine and Raspberry Ketone: Why No Central Effects?

Synephrine and raspberry ketone are structurally similar compounds found in Citrus Aurantium peel and Rubus Idaeus, respectively. Both compounds have a pharmacological profile that suggests that they cause lipolysis through activation of β3 adrenergic receptors. There is also likely some general adrenergic stimulation caused by affinity for other adrenergic receptors, and the exact pharmacology will depend on the compound of interest, with synephrine being composed of a number of structural isomers that differ slightly in their affinities for receptors. Further, capsaicin from the Capsiucum chili pepper also may have similar activity as it is structurally related to both synephrine and raspberry ketone. The basic structure of synephrine and raspberry ketones is that of a phenol ring with a side chain containing nitrogen. In this regard the structures are similar to central nervous stimulants including amphetamine and ephedrine. However, synephrine and raspberry ketones do not stimulate the central nervous system and this likely relates to their inability to cross the blood brain barrier. This may be because the hydroxyl group on the phenol ring in position 3 and 4 inhibits this activity. As amphetamine and ephedrine are not hydroxylated in either position 3 or 4 of the phenol ring, they can cross the blood brain barrier and provide significant stimulatory effects on the consumer. 

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Rossato, L. G., Costa, V. M., Limberger, R. P., de Lourdes Bastos, M. and Remião, F. 2011. Synephrine: from trace concentrations to massive consumption in weight-loss. Food and Chemical Toxicology. 49(1): 8-16

About Robert Barrington

Robert Barrington is a writer, nutritionist, lecturer and philosopher.
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