I have had some spare time to make up some theoretical chemistry about cactus to help people learn about alkaloid identification. This is for educational purposes only.

Extraction:

A/B (acetic acid acid NaOH base). Defat with xylene. Extract basic solution 5 or so times with CHCl3. Each CHCl3 rinse was rinse 2x with 1M HCl which was pooled and dried.

GC-MS:

We won't get into the instrument specifications. 6 mg crude HCl extract rebasified with 1mL 1M NaOH and extracted into 1mL toluene which was separated and rinsed 1mL water to remove base (base damages GC columns). 3ul injected into instrument.

4 peaks were present. (M+ is short for molecular ion. m/z means mass to charge ratio but its basically the mass of the ions that are present. base = base peak which is largest peak in spectrum often characteristic ion for compounds).

Mescaline major: m/z 211 (M+), 183(B), 167, 148, 107, 77.

Putative identification:

3,4-dimethoxyphenylethylamine: m/z 181 (M+), 152 (base), 137, 107, 91 and 77.

anhalinine: m/z 223 (M+), 222 (base), 208, 179, 151, 107, 77.

1,2,3,4-tetrahydroisoquinoline, 6,7,8-trimethoxy-1-methyl: m/z 237 (M+), 236, 222 (base), 207, 192, 161, 133.

Part two SWIM will think about what might happen if you rinse the crude material with acetone and IPA.

3,4-dimethoxyphenylethylamine has been reported in San pedro. The other two have been reported in cacti but SWIM is not sure if specifically san pedro. Its tough to dig through the references many are very old and hard to find. Correction: All the above except 1,2,3,4-tetrahydroisoquinoline, 6,7,8-trimethoxy-1-methyl have been reported in T. pachanoi. That ID could be something else perhaps or it could be correct. Impossible to say without references or more data.

oh yeahhhh haha awesome once again!

These tests are great and they cost time/effort/money, so its very appreciated..

Few questions: Is it possible to know the ratios of these alks? What about different sources of San Pedro? Would be interesting to test at least 2 different sources, maybe from some known/reputed vendor... All hypothetically of course, and knowing that even dreams cost so maybe some things cant be known for now




also, what about effect of any of these other alkaloids, is there anything known?

I'm really excited to see the rest of this test!!!!

Very interesting theoretical theoretical discussion I see going on here. VERY interested to see if the acetone +/- IPA washes (and IPA recrystallization? ) might remove the 3,4-DMPEA, anhalinine, etc.

Yes. There are two ways with GC. Get references for all compounds and make standard curves and quantify them. Or use a detector that has minimal variation in response factors for each compound. MS detectors tend to have large variation. So if one microgram of a compound A is injected you might get a million ions and if 1ug of compound B is injected you might get 3 million ions. So you can't compare rations. But with flame ionization detectors which are the most common GC detector the response variation is much much less with compounds of similar mass.



This would require a more quantitative extraction method. Doing A/B or STB will tell you the final composition but it might not reflect the actual concentration in the plant. This requires a series of tests to prove that your method is accurate reproducible quantitative etc. Perhaps someone has already developed such an extraction for quantitative analysis of cactus alkaloids. If not then it can be quite time consuming. So basically for screening large amounts of plants you'd want a simple easy and mostly exhaustive extraction.



DMPEA (3,4,dimethoxywhatever) is in Phikhal. They report no effects. Shulgin didn't do these tests he said some researchers did. He is surprised by lack of effects. SWIM has no idea about the others.

Also SWIM should note that the MS has no way of telling whether or not the methoxy groups are in the 3 and 4 position. Although biosynthetically this makes much more sense and its been reported before. But MS can't usually distinguish those kinds of substituents unless you do some really fancy tricks. Well sometimes you can tell because substituents position on aromatic rings tends to vary in stability etc. But yea its not so simple.