So I've been doing a little reading around and research on pinoline. The info out there seems pretty limited. A few in vitro and animal studies, mainly looking at its antioxidant capacity and other biochemical interactions, and it gets mentioned a lot on sites discussing darkness meditation and DMT, the pineal gland and mysticism.

Anyhow, it seems to me that this could be very interesting stuff to experiment with indeed. It would be fascinating to see how our endogenous MAOI would interact with our other endogenous tryptamines such as DMT, 5-MeO-DMT and bufotenine.

From Wikipedia:

Pinoline is a methoxylated tryptoline that occurs in the pineal gland during the metabolism of melatonin. Its chemical names are 5-methoxytryptoline and 6-methoxy-1,2,3,4-tetrahydro-β-carboline (6-MeO-THBC). The biological activity of this molecule is of interest as a potential free radical scavenger (antioxidant), similar to that function of melatonin.[1] It also acts as an endogenous MAOI.

From TiHKAL:

6-Methoxytetrahydro-b-carboline (6-MeO-THbC, pinoline) is a naturally occurring component of human blood and cerebral spinal fluid. Like 6-MeO-THH, it is readily formed from 5-methoxytryptamine, but with formaldehyde rather than with acetaldehyde. The levels have been found to be similar in schizophrenics and psychiatrically healthy patients, suggesting that it is not a factor in the chemistry of mental illness. It is a natural component of the human pineal gland and is quite effective in binding to serotonin sites in human platelets. It has been suggested that the balanced interplay between melatonin and pinoline in the manipulation of serotonin levels, might be an explanation of the sleep/dream state. The carbolines just might play an endogenous role in creating dreams, our "asleep" visual tripping.

&...

I have decided to completely eliminate the dosage, duration and qualitative comments for this compound, and all related harman analogues. The reason is painfully obvious -- virtually nothing is known about their psychopharmacology. Despite their enormous potential for someday being understood as possible intermediates in brain chemistry, they remain almost unexplored.


So it seems that the amino acid tryptophan is the precursor to melatonin and pinoline, so it can't hurt to make sure one is getting some tryptophan rich foods in their diet to provide their brains with the raw fuel for this stuff. It is structurally close to melatonin and the beta-carboline alkaloids harmine and harmaline. Glancing at the TiHKAL page it seems that conversion of melatonin into pinoline wouldn't be a straight forward affair to the laymen. I'm guessing this same applies if one would hope to convert harmine or harmaline into pinoline. Are any chemists able to chime in on this?

I've had a few experiences having woken in the night, after taking melatonin, having used DMT and most notably returning from Peru, having been introduced to ayahuasaca. These experiences were all distinctly psychoactive to some degree, they reminded me of caapi but were more subtle than that. I don't believe them to be the effects of melatonin per se, which to me doesn't seem to display much psychoactivity on its own but rather its metabolite pinoline. I also had an experience with 150mg Moclobemide + 125mg DMT fumarate + 3mg melatonin. After taking the melatonin, quite quickly there was a distinct shift in the nature of the experience...it became much more out of body, dreamy and blissful and there was a distinct twisting sensation or buzzing of energy around my third eye area that was distinct. I've read that during darkness retreats, melatonin levels build up after a few days, and once they cross a threshold pinoline production begins and builds up over the course of a few days, then once this reaches a certain threshold 5-Meo-DMT and DMT production can begin. This might be nothing more than hearsay, but I'm wondering if my prior experience occured because I was already MOAI'd up on the moclobemide, so when I took the melatonin, levels rapidly built up and led to pinoline production, which gave rise to the strong psychoactive effects experienced that are quite uncharacteristic of melatonin. I have felt something similar to this buzzing on iboga.

Animal tests seem to indicate pinoline has a psychoactive effect. I know one should be careful to extrapolate from such studies to humans, but can it be assumed that pinoline will have psychoactive effects in humans when ingested? It almost seems a bit bizarre to me that there isn't more interest in this compound and that there aren't more reports out there on human trials with it... Is anyone aware of any botanical sources of pinoline? I think Trout's Notes mentions it as being a trace component of some species of Desmodium. I know the botanical beta-carbolines seem to do the job very well of course, pinoline really intrigues me though being endogenous.

Seems like this could be a very interesting frontier to be explored.

Any thoughts on this stuff??

oh you and me brother..I would like to know more and get ahold this stuff. I have been reading everything I could find about pinoline for a few years and trying to find a source for it...

Phalaris grasses have tryptoline beta carbolines that are structurally similar to pinoline.