Pinoline

Pinoline, also known as 6-methoxytryptoline or as 6-methoxy-1,2,3,4-tetrahydro-β-carboline (6-MeO-THβC), is a β-carboline long-claimed to be produced in the pineal gland during the metabolism of melatonin, however its pineal occurrence remains controversial. Its more common name is a contraction of "pineal β-carboline". The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant, and as a monoamine oxidase A inhibitor.

Pinoline, also known as 6-methoxytryptoline or as 6-methoxy-1,2,3,4-tetrahydro-β-carboline (6-MeO-THβC), is a β-carboline long-claimed to be produced in the pineal gland during the metabolism of melatonin, however its pineal occurrence remains controversial. Its more common name is a contraction of "pineal β-carboline". The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant, and as a monoamine oxidase A inhibitor. Pinoline shows affinity for serotonin receptors, including the serotonin 5-HT 1A , 5-HT 2A , 5-HT 2B , 5-HT 2C , and 5-HT 7 receptors (K i = 156–4,335 nM). It is a high-efficacy partial agonist of the serotonin 5-HT 2A receptor, an antagonist of the serotonin 5-HT 2B receptor, and a full agonist of the serotonin 5-HT 2C receptor, with ( ) values of 2,140 nM (75%) at the serotonin 5-HT 2A receptor and 33 nM (95%) at the serotonin 5-HT 2C receptor and an of 1,120 nM at the serotonin 5-HT 2B receptor. Hence, pinoline appears to act as a potent and selective serotonin 5-HT 2C receptor agonist. The drug shows affinity for the serotonin transporter (SERT) (K i = 172–572 nM). It is a serotonin reuptake inhibitor, with an value of 1,100 nM. Pinoline shows affinity for the imidazoline I 2 receptor (K i = 1,640 nM) and for the α 2 -adrenergic receptor (K i = 7,830 nM). Conversely, it shows no affinity for the dopamine D 2 receptor (K i = >10,000 nM). The drug is a weak monoamine oxidase inhibitor (MAOI), with an value for inhibition of of 41,500 nM. Both pinoline and tryptoline partially substitute for the psychedelic drug LSD in rodent drug discrimination tests. The substitution by tryptoline was further assessed and was found to be blocked by the serotonin receptor antagonist pizotifen and by the serotonin synthesis inhibitor para-chlorophenylalanine (PCPA). Pinoline has also been reported to produce anxiogenic-like effects in rodents, which theoretically might be mediated by agonism of serotonin 5-HT 2C receptors. In addition, it has been reported to produce antidepressant-like effects in rodents.

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