Heimia Alkaloid Structures

[Auxin]

For years people have been having a hard time finding the structures of the Heimia salicifolia alkaloids, after wading through a bunch of old scientific journals I found them. Sofar I have transcribed the structures for the biphenyl type Heimia alkaloids (the main ones), as soon as I finish wading through some more journals and drawing them I'll also post the non-biphenyl alkaloid structures, then I'll work on a 'chemistry of heimia alkaloids' web page including info about TLC developers, alkaloid level manipulation, basics of the biosynthetic pathways, etc.

Pictures moved to my new http://hometown.aol.com/polyploid2/heimia/Heimia.htmlAlkaloids of Genus Heimia page.

[ 27. April 2003, 16:56: Message edited by: Auxin ]

[Darklight]

I wish I could draw like you

[Auxin]

"I wish I could draw like you"

:D

Sure am glad I remember my trigonometry or I could never have got the rings looking that good.

I knew Soh Cah Toa would come in handy

Befoer erowid spies start copying these pics it should be noted that I am gonna update these structures to include chirality at C-4 and C-10 (once I get the C-10 isomerism for each one confirmed by multiple sources). Also a few minor alkaloids are missing (I have the basic structure of anelisine, but cant find out the cis/trans isomerism ). Anyway, the pieces of the puzzle are starting to come together. I am getting some work done on the non-biphenyl alkaloids, but I'm not in a rush as it seems they disappear after the plants are two weeks old which would make them irrelevant as far as the Heimia brew is concerned because the plants are always older than two weeks when harvested.

I also found out about a third Heimia that has some of the same alkaloids plus some new ones. Anyone ever heard of Heimia montana? Its pretty new to western science (earliest reference I found sofar was from 1986) and I have not yet found reports about it being used by humans, but if nothing else it could provide some interesting data on biochemical pathways.

[bloodbob]

if those journels have the effects and relative strengths of the different compounds can you chuck them up too if its no trouble?

The heimidine looks interesting because out of the ones you listed its the only one with any real different chemistry.

[theobromos]

So, if you were to destructively distill some of these compounds (in a pipe, for example) what sort of changes might you expect? I would think the oxygens in the ester linkage could destroy the ring they are attached to and produce what could be regarded as a heavily-substituted phenethylamine. Perhaps not every time, but under certain favourable conditions. This is, of course, pure speculation based on other threads on the effects of smoking this plant.

Heimia montana was regarded as a subspecies of H. salicifolia. The previous discussion of this seems to have disappeared.

[bloodbob]

free oxygen radicals will attack just about everything

[Auxin]

I have not yet found the individual effects and relative strengths of those, but I am still looking (I'll be surprised if any list the effects we are looking for, or if more than one or two Heimia biphenylquinolizidine lactones have been tested for that, but we can always hope).

I still have to resolve the difference between heimidine and lythridine, the difference is odviously chirality at the carbon bearing the aliphatic hydroxyl, but I havent found definate configuration for either yet.

I dont know about the products from oxidative pyrolysis, that stuff gets pretty complex and it depends largely on temperature and level of oxidation. Ester pyrolysis should be expected to break the lactone into the conjugate acid and introduce a double bond into the ring. Another thing that should be expected to react is the phenol, but that gets a little more complex, also it would not be unlikely to have some degridation of the tirtiary nitrogen.

[woof woof woof]

Auxin, I need some chemistry lessons & a cool teacher, will you?

Hey why not a seperate chemistry site / forum for basic (alkaloid/plant) chemistry.

[ 03. April 2003, 06:55: Message edited by: brian ]

[theobromos]

Possibly splitting off the phenylpropene part?

[Auxin]

Before getting into chemistry talk, I'm half the way done updating those pics for optical isomerism- the new pics should be uploaded in nine hours (I found the difference between heimidine and lythridine, its optical isomerism at C-10 ).

Anyway...

"Possibly splitting off the phenylpropene part?"

Not really splitting off. The p-coumaric acid residue your refering to would possibly shatter starting at the phenol part and ester pyrolysis would seperate it from the quinolizidine portion. Once the phenol group decomposes there are numerous reactions that could happen, several of which would leave much of the broken p-coumaric acid residue connected to the other benzene ring. When the p-coumaric acid portion decomposes it also opens the door to polymerization so several alkaloidal and non-alkaloidal 'tars' would be formed.

Some of the alkaloids (like lyfoline) have phenol groups on both aromatic centers so those could really shatter when both phenols are disrupted.

[t st tantra]

curious about other lythraceae sp which have some of these and similar alkaloids,eg decodon,lythrum and lagerstroemia.

emboden says cryogenine is the most active alkaloid,it is anticholinergic,antispasmodic and tranquilizing.also experiments have shown effects stabilizing blood pressure and releiving experimentally induced anxiety states from the whole alkaloid complex.

t s t .

[Auxin]

Pictures moved to my new http://hometown.aol.com/polyploid2/heimia/Heimia.htmlAlkaloids of Genus Heimia page.

"emboden says cryogenine is the most active alkaloid"

First I'll assume they are refering to entheogenic effects, because it is not the best diuretic Heimia alkaloid (sometimes people forget Heimia has several medicinal uses).

Anyway, I think the jury is still out on that one, cryogenine (vertine) is the one in the highest concentration but there is a acknowledged descrepency between the effects of pure heimia alkaloids and the traditional brew, vertine does definatly hold promise though...

"Most of the animal studies discussed here have focused on the ataractic, antiinflammatory and antispasmodic potential of vertine"- Heimia salicifolia: a phytochemical and phytopharmacologic review. Malone MH, Rother A

You know what ataractic means dont you? It means it produces a perfect peace or calmness of mind: used especially to designate a detached serenity without depression of mental faculties or clouding of conciousness. Sounds sweet doesnt it? I'd like some of that before meditation (one instance where a lack of Heimia induced auditory hallucinations would be desierable ).

[ 27. April 2003, 16:57: Message edited by: Auxin ]

[bloodbob]

Okay thats good info you might be able to selectively condense/dehydrate heimidine to vertine. The esterification of the that free hydroxil group this could be done on just the bulk extraction of Heimia alkoids the only probably of course is the methoxide ion don't like water . My guess is if vertin is potentiated by having its free hydroxil group converted to a ester then the bulk should be even further pontentiated as vertin as its two substituants on the bottom ring are methyl esters. Then again a ester replacing the free hydroxil group my just make it worse :/

[t st tantra]

i'm finding objection to the term auditory hallucinations,i'd say sounds are greatly enhanced and then dealt with in a different way but never not there or distorted.it was more about relationship with aural environment and may be useful for deep meditation.

t s t .

[Auxin]

Yeah, it wouldnt be too hard to dehydrate heimidine because the resulting double bond is highly favored due to resonance, and the product would be mostly vertine under proper conditions (some trans isomer would sneak in though).

The methoxy groups at the bottom are methyl ethers, not esters. And you probably wouldnt want to mess with the phenols (hydroxyls at the bottom) at first because you'll notice that all of the alkaloids have a free hydroxyl on the p-coumaric acid portion (the lower ring on the right), so if you were looking for synthetic analogs that work would come later in the project.

I dont think we even need to think about synthetic analogs at this point because a lot of work remains to be done on the natural Heimia alkaloids first- you dont want to go into analog chem. blindly (plus I dont think any of us have the resources to do analog testing safely).

[bloodbob]

LOL @ me yeah I'm a bit tired and stressed from me IT project atm.

[Auxin]

OK, I've moved those pics to their new home:

http://hometown.aol.com/polyploid2/heimia/Heimia.htmlAlkaloids of Genus Heimia

I added pics depicting the origination of the atoms in the structures of the three different classes of Heimia alkaloids (if you water the plants with a solution of phenylalanine those same molecules become a major part of the alkaloids- it was proven with radioisotopes, bet ya didnt know that) and I started to put a little data in. Its all VERY crude at this point, I just wanted to get it on the net, mainly for the pics. Many upgrades are comming.

[ 27. April 2003, 16:58: Message edited by: Auxin ]

[Auxin]

 

http://hometown.aol.com/polyploid2/heimia/Heimia.htmlOK, I moved the page so people wouldnt stomp all over the SAB server. If you had it bookmarked you might want to update your bookmark.