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I Like to Draw Pictures of Random Molecules

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JacksinPA said:
The license period on my copy of ChemOffice 17 expired. Even though I own the earlier 11 version, that's for 32-bit machines & won't work in my Dell 64-bit Windows 7 desktop.

Perkin-Elmer wants over $2900 for ChemOffice 17. Even with the 20% discount they will give me for owning the earlier version, that's still $2500 or so for a program I only use occasionally.

I searched eBay for ChemOffice & found a guy in Spain selling ChemOffice 16 which is Windows 7 compatible. New, with download & license key. Listing #232946706683. For under $5. Three left. My experience with both versions 11 & 17 showed that they were basically the same structure drawing version of ChemDraw. I bought one. He has 3 left. Great value for $5!
Click to expand...

I finally received the download link + password to get into my ChemDraw Professional 16.0. I've been studying a group of structurally related perfume chemicals called irones. Here are the structures. The mixture is extremely expensive due to having to harvest & extract from flower bulbs, then let age for 2 years or so for enzymatic air oxidation. This method makes it too expensive for use in commercial perfumes. I've been running a patent search on synthetic approaches to manufacturing these at lower costs:

Irones.jpg


This is just a test of my new ChemDraw Professional 16.0 & it has all the functionality of my earlier 32-bit ChemDraw 11 & later 64-bit ChemDraw 17. The structures were generated by the program from the alphabetical names. Pretty neat! Saves the time needed to draw the structures manually.
 
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Jack, do u want all 3 isomer of irones, can they be as mixtures or only one isomer is desired in pure form?
 
I just stared downloading pdfs of the articles & patents on the irones this weekend so I haven't had time to get into them all. But it seems that one of the problems with making a good perfume-quality mixture is the ratio on the 3 isomers which is not going to be in the exact ratio of 1:1:1 due to both the structural dissimilarity of the isomers or their precursors & the structural specificity of the oxidizing enzymes(s). In Nature, where your letting the precursors extracted from Iris flower bulbs oxidize naturally, there is no problem getting an acceptable product but it is very expensive. Doing all 3 isomers in the lab & then mixing them to get an acceptable blend is the real challenge. Pure isomers are blended to get the final product. Because the final mixture is so expensive, a lot of work has been done on this by the big perfume companies.

It's a big relief to finally get ChemDraw back. They apparently only gave me a 6-month extension on ver. 17 in response to my helping with their beta-test.
 
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KROKODIL (Desomorphine)

This is a wide-spread opioid of abuse usually made via a 2-step reduction starting from codeine. It is structurally similar to morphine but lacks morphine's allylic alcohol function in what I have labeled as the 'C' ring.

DESOMORPHINE.jpg
 
Crocodile is far from desomorphine, while it is still main actives inside it.
The phosphorus and iodine compounds are not removedm thus very corrosive and make dead tissues, rotten flesh, falling off organs and degraded bones in users.
 
WO2009/106982 Pfizer 2009 CB-1 Receptor Agonists


AMB-FUBINACA.jpg


ADB-FUBINACA.jpg


I haven't gotten into this 289-page patent application yet but it is obvious that some serious medicinal chemistry effort went into designing these indazole compounds. The amide side chains are either esters or amides & have either alpha-isopropyl or -tert-butyl substituents. But the basic pharmacophore is 1-(4-fluorobenzyl)indazole in both.

Pfizer's work on synthetic cannabimimetics goes back over 40 years (1970s). These structures are new to me.
 
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Another 2009 Pfizer patent describes a series of benzimidazolone compounds with activity at CB1/CB2 but the exact mode of activity is not clear. Example 169 (pictured below) seems to be the most active based on the biological data given.

Example-169.jpg
 
It is a street drug & is prepared using some very nasty & corrosive reagents that may not be adequately removed before use. So I agree that desomorphine & KROKODIL may not be the same thing. Desomorphine in pure form is a long way from KROKODIL.
 
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CB. Receptor can accept vast array of molecule,
Align them using your chem 3D with these
- anandamide
- thc
- jwh-018 or similar
- fubinaca or similar

Put the tail together fixed at one spot, put the carbonamide of anandamide, phenolic OH of thc, and carbonyl of jwh and fubintogether,
and lock the bulk hydrophobic group together - the ene of anandamide, terpene of thc, naphthalene of jwh and aminoacid residue of fubi.

You can see the shape and requirement right there afterward, CB is quite a whore recepter (not pun, this is real word)
 
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5-bromo-DMT is found in certain underwater ocean sponges, ostensibly as an underwater weapon, and is likely psychoactive in its own right.

5-MeO-DMT can be had from milking the venom of giant leaping toads.

DMT:

Indole acetic acid (a common plant hormone) --> indole ethyl alcohol --> indole ethyl bromide --> DMT

I call this synthetic sequence THE BUTTERFLY RXN.
 
Dresden said:
5-bromo-DMT is found in certain underwater ocean sponges, ostensibly as an underwater weapon, and is likely psychoactive in its own right.

5-MeO-DMT can be had from milking the venom of giant leaping toads.

DMT:

Indole acetic acid (a common plant hormone) --> indole ethyl alcohol --> indole ethyl bromide --> DMT

I call this synthetic sequence THE BUTTERFLY RXN.
Click to expand...

The frog is an endangered species & hiking around the Sonoran Desert looking to capture one might cause you to acquire some stainless steel handcuffs from all the ICE in that area. Then how do you get them home & keep them alive? I understand they make a lot of noise.

I have no idea where & how you can find those sponges. Right ID = OK, bad ID = dead or very sick.

We've discussed starting from locally available tryptophan to make DMT. Could be a lot less expensive than IAA. And that reduction you propose involves some dangerous & hard-to-get reagents. And you can't get HBr at your local Walmart.
 
I have known of people who kept pet toads and milked them.

PBr3, actually.

But anyway, by all means, whatever reaction floats your boat. To me it's nothing.
 
Walmart doesn't stock PBr3 either. It's a very hazardous material that is a) difficult to obtain and b) require expertise in handling in specialized glassware with effective ventilation. To buy anything from Sigma-Aldrich you have to prove your a bona fide company. And I'm sure they report sales of certain materials to the DEA. Much easier to start with tryptophan from GNC.
 
Making HBr is not that daunting, food grade H3PO4 plus sodium bromide (pool supply store), mix & distill. Just don't do it in a spider-man coffee mug.

5-XYZ-tryptamines can also be easily made from 5-sub-indole a la Shulgin with oxalyl chloride intermediate. Assuming you have the lithal to do IAA->indole-ethanol.
 
sekio said:
Making HBr is not that daunting, food grade H3PO4 plus sodium bromide (pool supply store), mix & distill. Just don't do it in a spider-man coffee mug.

5-XYZ-tryptamines can also be easily made from 5-sub-indole a la Shulgin with oxalyl chloride intermediate. Assuming you have the lithal to do IAA->indole-ethanol.
Click to expand...

Oxalyl chloride is even nastier that PBr3. I think you were referring to PBr3 in the above.
 
Dresden said:
...indole ethyl alcohol --> indole ethyl bromide...
Click to expand...

The best conditions for that displacement, if one is trying to avoid noxious things, would be the Appel variant that uses triphenylphosphine and tetrabromomethane. It is not by any means atom-economic, but the reagents are crystalline solids and therefore much easier to deal with than bromine or phosphorus tribromide. Still not Wal-Mart specials, of course.
 
There are better variants of the Appel reaction... do they teach this concept of "atom economy" these days? Try for instance triphenylphosphine plus methyl iodide/methyl bromide. That actually ate the inconel off a thermocouple in the heated liquid state, good clean fun.

The fact that all the reactants in an appel reaction are crystalline is actually bad for scaling as you tend to form huge amounts of TPPO sludge... "real men" would use mesyl/benzensulfonyl chloride (liquid) or tosyl chloride (solid) instead to form a group you can displace with e.g. dimethyl amine.

If the tosylate is not suitably reactive then do a quicky finkelstein. R-O-Ts plus KI 1.3eq in DMF (or DMF/acetone mixture, the literature will tell you that you want NaI in acetone but ignore it and trust uncle sekio), heat at 50-60c with stirring, when you find there's no more precipitated KOTs then work up by adding cold water/crushed ice (dissolves KOTs, excess KI, and DMF/acetone) and extracting with suitable nonpolar solvent (less dense than water, maybe MEK or IBK for polars? ether works fine for most iodides). Decolorize product with sodium sulfite or the like then dry the nonpolars and pop on a rotovap, bam, 80% yield every time

indol-3-yl-N,N-dimethylglyoxylamides are the intermediates used in TiHKAL for a lot of tryptamine synthesis. You don't need neat oxalyl chloride, the 2M solutions people sell for Swern rxns will work fine too. Oxalyl is smelly but has good atom economy due to low equivalent m.w.
 
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