Hehe understandable. SWIM should have everything repaired sometime next week.

men....i just wanted to say that it is truly awesome to read all of your collective chemical genius batting these ideas around. it is because of YOU that we are all able to enjoy these righteous fruits of your labors. just wanted to thank you all from the bottom of my frontal,parietal,temporal and occipital lobes.

LOVE AND GRATITUDE!

Have SWIY had the opportunity to analyze the inactive Bufotenin solution yet, burnt?

Nope got side tracked with other projects Haven't forgotten though.

FYI: Dehydrobufotenine is a zwitterion. It cannot be freebased.

When SWIM had left his bufotenine to mix in calcium hydroxide for 24 hours, the resulting compound could NOT be freebased. That indicates dehydrobufotenine was made and that Shulgin's theory is right. I would like to see someone test this out to be certain of this reaction.

Dehydrobufotenine has an XLogP3 of 2.3 , while bufotenine has an XLogP3 of 1.2. That means that dehydrobufotenine should cross the blood brain barrier better than bufotenine. Now the results of mixing bufotenine with calcium hydroxide for 24 hours produces a non-smokeable result, but it was never tested sublingually or orally. It’s possible that dehydrobufotenine is active sublingually, orally, or by insufflation. SWIM never tried those routes of ingestion with this substance, he only tried smoking it.

Has anyone else made this and tested its activity other than by smoking it?

hmmmm...that is a interesting idea 69ron....SWIM may just have to try out converting some bufo and testing it....would you think that maybe 25mg might be a good starting place for sublingual then to swallow?

That sounds good to me. Whatever the potency is, it’s most likely weaker because snuff left to react for 24 hours is usually said to be weaker not stronger.

By the way, you can safely orally ingest up to 1000 mg of calcium hydroxide per day. Up to 1000 mg of calcium hydroxide is found in some OTC calcium supplements. So don’t worry about traces of food grade calcium hydroxide left in it. You could actually mix 25 mg calcium hydroxide with 25 mg bufotenine in water for 1 day and simply ingest it orally as is without separating it. But if using it sublingually, you’d better separate it because the calcium hydroxide is going to burn like crazy (unlike the stomach, there’s no hydrochloric acid in the mouth to counteract it’s alkalinity).

I bet it’s orally active.

coool

hey, bufo freebase is soluble in ipa and acetone, check this thread

It strikes me that a methyl group might easily transfer from the quaternary nitrogen to the hydroxy group very close nearby via a five-membered cyclic transition state. This would yield O-methylnordehydrobufotenine -the cyclised equivalent of 5-MeO-NMT, which Shulgin mentioned somewhere. That's a molecule that looks like it would be active, too.

This passage appears in my printed copy of TIHKAL, however erowid's online version of TIHKAL left this last paragraph out, I'm not sure why, it was probably a mistake:



More related information concerning potential activity of O-methylnordehydrobufotenine:


We discussed something very similar in THIS thread sometime back, so I'm sorry if this is too similar to post 9 of that thread, but it is relevant here well.

Structurally O-methylnordehydrobufotenine is quite similar to RU-28306 or Bay R 1531 or even LY-293284. RU-28306 being the most interesting in my mind. When I was younger, and had first noticed the mono-methyl-tryptamine moiety burried within the LSD molecule, I figured that if you could add a second methyl group to nitrogen 6 of LSD that you would in turn produce a molecule which would essentially be LSD with a dimethyltryptamine moiety burried within it, but the nitrogen at position 6 of LSD does not have any available valence electrons to facilitate adding this additional nitrogen, so the idea died there, however, RU-28306 could be seen as an LSD/DMT moiety combination, only an entire ring structure had to be basically removed.



There really is not much useful information regarding RU-28306, when I searched all I found was some individuals on sites which I do not use, who seemed to be seeking to get intoxicated, who asking about it, completely useless. As far as research information, not much is out there, I think I remember having had an article or two, but can not locate them.

Brief info on the other tricyclic tryptamine which is structurally similar to O-methylnordehydrobufotenine, bay R 1531.


It's been a while since I have done research regarding these molecules...I have actually learned a ton since the last time I had posted regarding these compounds, the funny thing was, school was only good for the basics, and I was not learning very efficiently, I also could not mention anything relating to psychedelic or psychoactive chemistry in school or to my professors for obvious reasons. It was not until I started working with other chemists outside of school that I really began to learn, I recently took on an apprenticeship with a retired organic chemistry professor, who has a fairly nice laboratory. It was through this recent one on one and hands on learning that I really began to excel and grow at the art of organic chemistry. In the last year and a half I have made more progress than I did with 3 years in school. Though it's all beneficial in the end, every day I learn something new and progress a little further.

Any way, this is getting lengthy and I'm straying off topic periodically, so I will stop here.

Pictures attached are O-methylnordehydrobufotenine, RU-28306 and Bay R 1531.

-eg

Thanks. That's exactly what I was thinking of, although perhaps a link to the other thread would have sufficed for the latter part

That BAYR 1531 is also a dipropylaminotetralin (DPAT) derivative. DPAT derivatives also have some interesting properties. Some fall into the class known as 'serenics', for example.

I'm sure a good deal of these 5HT1 agonists will prove to be "serenic" in nature, as long as its an "agonist that mainly acts on the postsynaptic 5-HT(1A/1B) receptor sites"...



I'm still quite interested in O-Methylnordehydrobufotenine, as well as RU-28306.

Just curious, Are there any 12-methoxy substituted LSD homologues? Or 12 substituted lysergamide compounds in general?

-eg

If you feel the later part is not necessary, I would gladly remove it to improve the thread, just let me know.

-eg

I've often wondered this myself. Kind of the LSD equivalent of 5-MeO-DMT. That's an area of my literature research that really ought to move forward.

To some extent this ties in as well with David Nichols' work where it was found that LSD is metabolised by certain people to form 13-hydroxy-LSD which is a potent dopaminergic agonist and has been linked to the 'dark' aspect that possibly these same certain people experience in the latter part of an LSD trip? Somewhere there's a video where Nichols covers this.

Interesting. Thanks.

I'm actually surprised more has not been done regarding this matter.

I've noticed the last few hours of an LSD experience can be almost amphetamine like, LSD itself does affect dopamine receptor subtypes, as well as adrenoreceptor subtypes, and I've always assumed that this was the source of the stimulant effect encountered in the later LSD experience. I had not considered metabolites, and since this effect is occurs in the later end of the experience this would have been logical.

I'll search out the Nichols video.

-eg

This one, particularly at t=43.36

Or t=47.18 for really cutting to the chase.

Awesome, thanks.

I always take Sundays off the nexus, so Monday there's a good deal to read and write, I would have gotten to this faster otherwise, again, thanks.

-eg

Heh, you're welcome - it gave me something to do while I was feeling really lousy!