spectrasonic
Greenlighter
- Joined
- Nov 24, 2007
- Messages
- 39
I've recently been checking out Turin's patents - there's quite a few of them (check gb.espacenet.com) and perhaps the most significant section of his deals with those modifications that can be performed to molecules whilst keeping their vibrational properties similar to the original, but increasing intensity and other changes. You really need to all check out many of the patents for their drawings, particularly "Fragrance compositions comprising benzo[4,5]thieno{3,2-b]pyran-2-one". It appears to my limited understanding that there could be an incredible number of new compounds via these routes.
The only things I searched for - thiophene analogs of amphetamine and DMT appear to be active. Hopefully someone with plenty of chemical/pharmacology knowledge will be able to tell us which of these are applicable and which aren't.
From "Method for increasing the stability and intensity of odorant molecules" patent:
"There are certain odorant substructures which can be interchanged without significantly effecting odor character. Isodonic replacements include, without limitation, aldehyde-nitrile replacement, aldehyde-methyl ether replacement, aldehyde-acetal replacement, ene-cyclopropane replacement, ene-oxirane replacement, ene-thiirane replacement, ene-thioether replacement, isobutenyl-phenyl replacement, isobutenyl-dimethyl cyclopropyl replacement, phenyl-dimethyl cyclopropyl replacement and benzene-thiophene replacement. These replacements are discussed in more detail below.
Double-bond Replacements and their Effect on Odor
Many aromachemicals include an isoprenyl unit and/or other C.dbd.C double bonds. The C.dbd.C double bonds can be replaced by thioether groups, --S--, without marked change in odor character. Alternatively, the carbon double bond can be replaced with a thiirane ring. In these embodiments, the lone pair of electrons on sulfur binds readily to Zn, which increases the odor intensity without significantly altering the odor type.
One or more (if present) C.dbd.C double bonds in an aromachemical can be replaced with cyclopropane, oxirane (OX), or thiirane (TH) moieties. The odor of the compounds remains substantially the same with this substitution, whereas the odorant intensity can be dramatically improved. The odorant intensity can be determined by measuring zinc binding affinity, for example, using the techniques described in Rakow N A, Suslick K S. A colorimetric sensor array for odor visualization. Nature. 2000 Aug. 17;406(6797):710-3., although other methods are available. All four 3-membered rings described above can coordinate to a zinc ion, but they do so in two different fashions. The cyclopropyl group coordinates via its C--C bonds which, because of the strained geometry, have a partial pi character. The three heterocycles coordinate by more conventional lone pair bonding. The 3-membered rings are shown here coordinated to a zinc ion in turn bound to an imidazole ring, which represents the histidine known to be involved in biological binding of zinc to olfactory receptors. The binding energies, as calculated by both semiempirical and ab initio methods are in the following order: TH>CP>DB>OX, wherein DB is the C.dbd.C double bond. Based on the binding energies, it is expected that thiirane and cyclopropane derivatives will bind better to zinc than the C.dbd.C double bond. However, there are other considerations, of course, which enter into the overall affinity of the odorant for its receptor, including but not limited to hydrophobicity, steric hindrance, and the like. The thiirane derivative appears to be the most stable derivative chemically."
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