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Possible to turn alkaloid to terpenoid but keep activity?

Nagelfar

Bluelight Crew
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Straight question. Could one make a terpenoid cocaine functional analog or a THC alkaloid functionl analog? If so, any examples? Hygroscopic cannabinoids and lipophillic dopaminergics?
 
Do you really mean terpenoid or do you actually mean hydrocarbon? Terpenoid sort of implies it's constructed from isoprene units, hydrocarbon is the more general term for C, H only.

There are definitely amine analogs of THC, the three classes I can immediately think of being either replacement of the benzopyran ring with a benzoquinoline ring a la levonantradol. adding amine groups to the free phenolic OH somehow (O-1057) or adding amines onto the alkyl "tail" like O-2545.

As for fully hydrocarbon analogs of cocaine, tropoxane seems to be the closest I can think of.

To be truthful, THC is only half terpene. The olivetolic acid group (i.e. the olivetol group - aka 1,3 dihydroxy 5 pentyl benzene) is produced by polyketide synthesis.
And cocaine is not terpene at all: it's derived from amino acids (lysine, phenylalanine, methionine) if I remember right.
 
I was using cocaine as an example of an alkaloid, but yes more terpenoid structure, any isoprene DRI type, lipophilic drugs?
 
That's a mystery. But just know terpenes are easily identified by their empirical formula, which tends to be some multiple of C5H8, e.g. C5H8 (hemiterpenes), C10H16 (monoterpenes), C15H24 (sesquiterpenes), C20H32 (diterpenes). Add NH for every amine or O for every alcohol. Subtract 2 H and add 1 O for ketones.

A structure search of C10H17N, or C15H25N give or take multiples of 2 hydrogens and possibly an oxygen, would be enlightening as a starting point. From there, look for isoprene skeletons or suitable rearrangement products of same.
 
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