Theoretical report:

So SWIM decided to get analytical on some jungle spice. injected some more into GC-MS and started looking at the mass spectra of some of the minor components. Note that again dmt again was the major SWIM repeats major component of this mixture. SWIM found a minor peak with a mass of 186 whose spectra matched with 1-methyl-1 2,3,4-tetrahydro-beta-carboline and also evidence for a quinione with methyl substituent peak which could maybe be a break down product of the above beta carboline. also note that the peak shape is very strange for this beta-carboline suggesting that it is actually a bigger molecule falling apart because if you look at the later parts of the peak more ions appear with higher mass the other masses are: 207, 341 (base peak), 475 (also 477 which is the same as yuramamine), and 563. note that the fragmentation of this molecule does not match yuramamine at all but this could be because its falling apart or some other similar artifact is formed and thats whats being seen.

so now SWIMs thoughts. the concentration doesnt make much sense dmt is by far the major component and this peak is basically a trace component barely above the baseline. could this compound be that active!? if so SWIM should not be posting here but publishing haha. but anyway also we could be seeing a sort of half volatilized compound, the temperature used to inject was 290 degrees C so if the main compound has a higher mass then 186 and 186 is just an artifact from heating then this compound as a whole SWIM doubts would be vaporized when smoking jungle spice because DMT vaporizes at much lower temperatures. but the compound could break down and lead to these weird structures SWIM has observed. anyway it appears that jungle spice when analyzed by GC-MS contains trace amounts of a beta carboline like structure which is most likely an artifact resulting from the degradation of either DMT or yuramamine like compound. LC-MS should answer the temperature problems but alas SWIM has not the time to do that theoretical analysis (for now).

anyone know anything about the biological activity of this beta carboline also has anyone tried injesting jungle spice orally?

Interesting. 1-methyl-1,2,3,4-tetrahydro-beta-carboline is also found in Diploterys cabrerana.

SWIM has had "Jungle Spice" effects occasionally from Diploterys cabrerana extracted with DCM. I think this is the chemical responsible for "Jungle Spice" and it simply alters the effects of DMT and increases its potency. The “Jungle Spice” effects SWIM experienced from a Diploterys cabrerana extract was after the 5-MeO-DMT was removed from it.

I am pretty sure this is the "Jungle Spice" compound and it’s most likely also responsible for orally activating the DMT in jurema prepared without an added MAOI.

Like mimosa, Diploterys cabrerana is also orally active without MAOI, but at higher doses.

Very nice data, well done!

I wonder whether you could attach the MS output for us to study it as well. SWIM also thinks that HPLC-MS is the way to go, GS already seems to give plenty of artefactual results...

As for the chemical nature of jungle spice, SWIM is currently theorising on their pharmacokinetics; whatever is inside the jungle spice seems to be exerting a unique synergy with dmt (or so to speak the principal compound). Or it could be the case that by smoking jungle spice one gets the effects primarily from this compound. And that is because the concentration of this beta-carboline (or whatever that may be) certainly does not give any clues about its activity.

Would a Manske precipitation work in purifying this beta carboline?

SWIM thinks it needs to bioassayed alone! It maybe the case that it does more than just a MAO inhibition. SWIM is just theorising on a "super" compound that can produce intense psychedelic experiences (sth like a "vaporised" LSD something!)

Again, very good work!

The Manske tech extracts harmine and harmaline specifically. I know it doesn’t work with harmalol or harmol, and probably also doesn’t work for THH, so I doubt it will work for 1-methyl-1,2,3,4-tetrahydro-beta-carboline. But then again, you never know for sure until you try it. SWIM found that the Manske tech works for DMT, but not that well.

Here are some alternate names for 1-methyl-1,2,3,4-tetrahydro-beta-carboline:

Tetrahydroharman (the most popular name for this compound)
Tetrahydroharmane
Methtryptoline
1,2,3,4-Tetrahydroharmane
1,2,3,4-Tetrahydroharman
Harman, 1,2,3,4-tetrahydro-
2,3,4,9-Tetrahydro-1-methyl-1H-pyrido(3,4-b)indole
1H-Pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-1-methyl- (8CI)(9CI)
N-Methyl-H4-β-carboline
N-methyltetrahydro-beta-carboline
1-methyltetrahydro-β-carboline
1-methyl-1,2,3,4-tetrahydro-β-carboline
1-me-tetrahydro-β-carboline

Here is the image of tetrahydroharman:

Here’s harmaline:

Here’s DMT:


To me tetrahydroharman visually looks like a cross between harmaline and DMT. Imagine DMT with its tail wrapped around and attached to the indole ring, you’d have something like tetrahydroharman. Like DMT, tetrahydroharman doesn’t have a methoxy group hanging off of the indole ring. Harmine, THH, and harmaline all have a methoxy group hanging off of the indole ring. I’m sure the absence of a methoxy group dramatically changes the effects (for example, 5-methoxy-DMT and DMT have very different effects). SWIM finds the poor visual effects of 5-methoxy-DMT similar to harmaline. Is this because of the methoxy group? Hmmm. Maybe tetrahydroharman is more visual than harmaline because it lacks the methoxy group like DMT? A hydroxyl group on that side increases visual effects (like 5-HO-DMT and 4-HO-DMT), but a methoxy group there seems to decrease visual effects (like 5-MeO-DMT). Is this just all coincidence?

Tetrahydroharman is found in Diplotperys cabrerana and seems to also be found in Mimosa hostilis. It is said to be a weak MAOI. However, both Diplotperys cabrerana and Mimosa hostilis are orally active without an additional MAOI, but at higher doses, and in each, tetrahydroharman should only be present in trace amounts. As I understand it, tetrahydroharman is the only beta-carboline present in Diplotperys cabrerana. It may be a weak MAOI, but may also be itself highly psychedelic like DMT because it lacks the methoxy group. And according to it’s structure, it should be orally active without additional MAOI.

I would love to find out if tetrahydroharman is psychedelically active in humans! I bet it is more visual than the other beta-carbolines.

Here’s the image of tetrahydroharmine (THH):

Here’s an image of harmine:

Here’s 5-MeO-DMT:

Here’s 5-HO-DMT:




Harmaline has an XlogP of 0.8. Tetrahydroharman has an XlogP of 2.0. Tetrahydroharman should therefore be much more lipid soluble than Harmaline. That could mean it’s also many times more potent than harmaline. DMT has an XlogP of 2.0 just like tetrahydroharman. So the solubility profile of tetrahydroharman should be more similar to DMT than harmaline.

What is known about tetrahydroharman:

* Melting Point: 144-148 C (R-form), 179-180 C (-+ form) (see Dictionary of Alkaloids By Ian W. Southon, Geoffrey A. Cordell, J. Buckingham, page 1043)
* Produced as a condensation product of tryptamine and acetaldehyde.
* Acts as an MAOI. Said to be a weak MAOI (see http://www.erowid.org/li...a/aya_sec1_dosages.shtml)
* Found in the human body (See TiHKAL #44. 6-MEO-THH).
* Said to be a sedative in animals (see http://www.erowid.org/li..._sec1_harmala_isol.shtml)
* Found in many plants including: Hammada leptoclada (Pop) Iljin, Petalostylis labicheoides, Elaeagnus hortensis, Elaeagnus orientatesm, Elaeagnus spinosa, Arundo donax, Acacia baileyanna, Acacia complanata, Petalostylis labicheoides, Petalostylis labicheoides (also has N,N-DMT), Peganum harmala, Diplopterys cabrerana, Banisteriopsis argentea.
* Look at this interesting bit of data on it: “…the Gimi of the New Guinea Highlands pass into a trancelike state during divination rites by smoking a mixture of tobacco with leaves of an Elaeagnus species (Glick 1967). The genus Elaeagnus is rich in beta-carbolines such as tetrahydroharman (Hegnauer 1966; Allen and Holmstedt 1980)…”

One problem in researching tetrahydroharman is that some people misspell tetrahydroharmine as tetrahydroharman because the spelling is so similar!

Well, there’s next to no information on the human toxicology of tetrahydroharman. It could very well be active, especially by smoking. Most of the beta-carbolines are more effective when smoked.

Jonathan Ott reports that 7.5 mg harmaline is effective as an MAOI when snuffed or taken sublingually. That’s a very low dose. Ott reports the oral MAOI dose needed for HIM is about 40 mg harmaline. Most people need about 75 mg – 100 mg. But everyone is different. Perhaps tetrahydroharman is active as an MAOI at as little as 1 mg when smoked? That could explain the “Jungle Spice” effect SWIM got from smoking 5 mg of a Diplopterys cabrerana alkaloid extract.

If the “Jungle Spice” effect is from a mix of tetrahydroharman and DMT, and the interaction is from the MAOI effects of tetrahydroharman, then why is the trip so short? Shouldn’t the trip last about 1 hour and have a slower onset? I think it is maybe not MAOI at play here. The “Jungle Spice” effect is not at all the same as harmine + DMT. So I think that possibly tetrahydroharman is itself contributing strong psychedelic effects and it may be much stronger that DMT, 5-MeO-DMT, and 5-HO-DMT. It occurs in such low quantities that in order to feel it’s effects it must be very potent.

All of this is of course theory. I would very much like to se tetrahydroharman tested in man. How can you isolate it?

hmm...

swim may have inadvertently synthed some tetrahydroharman back in '06 from tryptophan, by refluxing with cyclohexanol and cyclohexanone, then methylating.

Was it active?

swim would say so.. definite body buzz, and about 8 minutes of vague CEVs, mainly shifting colored sine waves and patterns. swim would imagine there might have been a small amount of dmt in it, but mostly beta-carbolines

although i love this discussion we should also be very careful discussing the psycho-activity of these compounds. it may give certain governments an excuse to ban this compound and plants containing it. seriously its something to think about.

anyway THH can easily be made from other beta carbolines that are much easier to isolate. i forget how to do it but i think its just heating in acid. something rather simple. oops sorry SWIM mixed up THH with the tetrahydroharman. then yea SWIMMERs need another way to get it. by THH SWIM meant tetrahydroharmaline haha, ah nomenclature.

SWIM think the idea that some compound is synergising with DMT in jungle spice is a very resonable possibility. MS isn't good to determine concentrations without reference standards so SWIM can't say for sure how much is in this mixture with this method and yea LC-with UV-MS would be better at least for comparative purposes. but yea the likely hood that its an MAOI effect is small. if the mix is active orally them maybe its an MAOI effect but then the concentration is too low and suggests that this tetrahydroharman is just an artifact of perhaps something not being seen in the MS spectrum. unless tetrahydroharman is orally active on its own also.

anyway SWIM will try to post a copy of the spectrum does anyone know how to post shit like that?

HA HA HA. I see this all the time. Even from respectable authors. And you did it again. THH is tetrahydroharmine, not tetrahydroharmaline which doesn’t exists, and this other one were’re talking about is tetrahydroharmane or tetrahydroharman. All it takes is to accidentally swap an “a” for an “i” near the end and you're talking about the wrong chemical! Actually I like the name methtryptoline more because it's less confusing, but few people call it that.

I think tetrahydroharman is active. SWIM tried harmalol once and experienced a short mushroom like trip. The effects were nothing like harmine or harmaline.

Here’s a pic of harmalol:

Compare that with tetrahydroharman (methtryptoline):

Compare that with harmine:

See how similar tetrahydroharman is to harmalol. Harmalol’s effects are nothing like harmine or harmaline. SWIM never tried a large dose of harmalol and only did it once, but he remembers it was like a very short mild mushroom trip that lasted about 90 minutes. He only got very mild visuals from it, but the dose was very low. He would like to try it at a larger dose someday. Harmalol doesn’t have a methoxy group like harmine or harmaline. The main difference between harmalol and tetrahydroharman is that harmalol has an additional oxygen atom on the indole ring making it more water soluble with an XlogP of 0.4 while tetrahydroharman has an XlogP of 2.0. Theoretically, because tetrahydroharman is more lipid soluble than harmalol, its probably far more psychoactive. Like tetrahydroharman, harmalol is a weak MAOI. Also harmalol feels like a true psychedelic at low doses, feeling a lot like a low dose of psilocin (again SWIM never tried a large enough dose for visuals). SWIM could easily have mistaken it for a low dose of psilocin. The body feeling and the euphoria was the same.

Can you post it as an image? That would be easy.

thats exactly what I thought of and asked in some other thread (forgot where) but someone said that jungle spice was tested orally and it is not active..

so questions to be asked: if this beta carboline in jungle spice is responsible for pure jurema activity, then how does this explain the fact that for jurema to be active by itself it needs to be a cold water infusion, without acid and heat? Dont people exactly heat up AND use acid when making extraction, and still get jungle spice in the end?



new information, never heard of that.. interesting... want to estimate doses (even though obviously it all depends on the batch you have and so on) ?

That was probably me....however, jungle spice is NOT orally active mimosa. Orally active mimosa is made by cold water infusion. Jungle spice is extacted from heated, or highly basified MHRB before extraction. My guess is that all of the chemicals that are found in cold water extracted Mimosa are not the same as the chemicals found in jungle spice. In fact, my understanding is that different teks will give different types of jungle spice. A STB extraction does not give the same jungle spice as an A/B extraction. Again this is only what I have read, I have only done one jungle spice extraction and did not find it to my liking.

The reports that I have read about oral jungle spice has said that even at high doses (200+mgs) there was very little activity. I personally have not tested oral jungle spice or cold water extracted Mimosa, so I am only going on reports I have read.

SWIM has noticed a very distinct similarity between the visuals of 5-methoxy-DMT and 7-methoxy-harmalan (which is actually harmaline) and believes it is related to the methoxy group on the indole ring. That group seems to prevent full on visuals from manifesting keeping the visuals dark and like that of a daydream.

Here’s an image of harmalan:



Here’s an image of harmaline (7-methoxy-harmalan):



The difference between harmalan and harmaline is similar to the difference between DMT and 5-methoxy-DMT. Harmine, harmaline, and THH all have that same methoxy group and they all produce visuals that are dark and distance like 5-methoxy-DMT visuals.

SWIM theorizes that harmalan should be more visual than 7-methoxy-harmalan (harmaline) based on that reasoning. SWIM never tried harmalan though. Has anyone else tried it?

Like harmalan, tetrahydroharman (methtryptoline) has no methoxy group on the indole ring, but it is more lipid soluble than harmalan and should be more psychoactive than harmalan.

Here are the XlogPs of the b-carbolines discussed:
2.5 - harmine
2.0 - tetrahydroharman (methtryptoline)
1.9 - tetrahydroharmine (THH)
0.8 - harmaline
0.8 - harmalan
0.4 - harmalol

B-carbolines with a methoxy group on potision 7 of the indole ring:
Harmaline
Harmine
Tetrahydroharmine (THH)

B-carbolines with oxygen at position 7 of the indole ring:
Harmalol

B-carbolines with nothing at position 7 of the indole ring:
Tetrahydroharman (methtryptoline)
Harmalan

DMT is highly visual.
5-HO-DMT is highly visual (when smoked as freebase, and apparently not when injected as a salt).
4-HO-DMT is highly visual.
5-methoxy-DMT is hardly visual at all but very psychedelic.
7-methoxy-DMT is said to be inactive.
6-methoxy-DMT is said to be inactive.
4-methoxy-DMT is said to be inactive.
DPT is highly visual.
5-methoxy-DPT is hardly visual at all.

DET is highly visual.
4-HO-DET is highly visual.
5-methoxy-DET is hardly visual at all.

A methoxy group seems to mess up the visuals or even cause inactivity. Harmine and harmaline are definitely psychedelic in their own way, but both lack strong visuals. Their visuals are mostly like that of 5-MeO-DMT in that they are dark and distant. At high doses visual looping is present as with 5-MeO-DMT causing “trails” or “tracers”, and there’s some light visual patterning, etc. It’s very much like 5-MeO-DMT.

Do you see what I’m getting at? Judging by the chemical structure, tetrahydroharman is the most like DMT of all the beta-carbolines I’ve listed in this thread and the others are more like 5-methoxy-DMT. Tetrahydroharman is also highly lipid soluble so it should easily cross the blood brain barrier so it should be relatively potent. It should also be orally active just like the other b-carbolines are.

What about 5-MEO-MIPT? This one is very visual at doses above 15mgs.

Probably the exception to the rule?

this is an awesome thread

That could be a good explanation, a bigger molecule breaking down. That could expain why even some experienced people have unfavorable results when extracting jungle spice. Are the visuals really that drastically different? I've kind of always assumed that this might just be some kind of reaction with plant oils and more of mind over matter at play because the spice looks more menacing.

I'm sure there are exceptions to the rule. I don't know much about 5-MEO-MIPT so I can't really comment on it. In general most methoxy versions of hallucinogenic drugs are less visual then their parent alkaloids.

I’m really curious to know if anyone has tested any of the non methoxy beta-carbonlines like harmalol, harmol, harman, harmalan, and tetrahydroharman (methtryptoline). TiHKAL states that harman is inactive at up to 250 mg orally. Harmalol produces sexual stimulation in rats.

In the one test my friend did with pure harmalol, he said it was like psilocin and nothing like harmine or harmaline. I can’t find any text book reports of its use in humans. The same is true for harman, harmalan and tetrahydroharman. All of the activity reports are from harmine and harmaline, which both have 7-methoxy groups and as I’ve shown above, the addition of a methoxy group on the indole ring usually hinders visual activity for most tryptamines. But that might mean nothing for beta-carbolines.

Guiera senegalensis contains harman, tetrahydroharman, harmalan, all of which have no methoxy group.

Here’s the structure for harman:



Here’s the structure for harmol:


Is Guiera senegalensis hallucinogenic? Look at this

It appears that Guiera senegalensis is active at least as a sedative. But is it hallucinogenic? We can’t tell by animals tests.

What does this mean: “attenuated amphetamine-induced stereotype behavior in rats”?

alright i have been having trouble posting these spectra without making the images look like crap so i'm going to post them as tiff attachments, so you can download and examine. alright thats making the images look like shit too so i'm going to post the whole mess of spectra as a powerpoint file ill label all the things nicely for ya'll. if someone can figure out how to post these things please explain or help i'm bad at these kind of things.

anyway enjoy the theoretical report. remember most of what I say is all lies and bullshit.

There is more empirical indication for a MAOI in MHRB coming from SWIM's latest jungle spice extraction:

Extraction:

Briefly, STB was performed on MHRB, pulled with xylene and alkaloids were precipitated out using fumaric acid saturated acetone. Fumarate alkaloids were collected, dissolved in water and the solution was basified. Clouds of precipitation were collected using a centrifuge. These freebased alkaloids were washed with naphtha to get dmt out, leaving all the rest alkaloids (thereafter called "jungle spice" ) behind.

This "jungle spice" wouldn't solidify, even after it was dissolved in acetone and acetone was left to evaporate. Not a big problem however, it finally was absorbed onto some parsley leaves.

Bioassay:

Enhanced parsley leaves corresponding to 10mg "jungle spice" were smoked.

No effect whatsoever, followed by the slight disappointment that comes from failed lift-offs

So SWIM decided to smoke 40mg dmt.

The trip was much more intense than anticipated. After the eyes were opened OEVs continued for a good 40min. They were also frightening and uncomfortable at times.

The total duration of the effect and the afterglow were reminiscent to SWIM of the combination of eaten harmala alkaloids and smoked dmt and of fumahuasca.

This was repeated the very next day and very similar observations were made.

SWIM's "jungle spice" has MAOI activity.

Your tests show it to most likely be an MAOI causing the “Jungle Spice” effect. It sounds to me like tetrahydroharman (1-methyl-1,2,3,4-tetrahydro-beta-carboline) is most likely responsible for the “Jungle Spice” effect. That explains why some Diplopterys extracted with DCM also produces the “Jungle Spice” effect in SWIM. Some strains of Diplopterys are higher in tetrahydroharman than others.

NOTE: I want to be clear here, tetrahydroharman is not to be confused with tetrahydroharmine (THH) which is a different compound that is present in caapi. Tetrahydroharman is found in Mimosa and Diplopterys and not found in caapi.

It could be that the betacarboline is slightly altered by the heating, but still remains an active betacarboline with slightly different effects. For example, boiling harmaline with fuming hydrochloric acid produces harmalol, which is also active but has different effects.



The dosage needed for Diploterys cabrerana to be active orally without MAOI is about 10 times the normal dosage needed with an MAOI. But this depends on the strain used. Some strains are inactive without an MAOI. This is probably because the tetrahydroharman content varies from strain to strain.