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ARCHIVE:  April 2, 2001

THC and Lichens

Dear Dr. Shulgin:

In PIHKAL you have mentioned that the chemicals obtained from lichens can easily be brought to react with certain essential oils from natural sources, to make synthetic tetrahydrocannabinol.  Are there more detailed references to this process beyond what is in your book? –Tengu

Dear Tengu:

There certainly are! The tetrahydrocannabinol molecule from Cannabis can be viewed as a combination of two very different halves. 

The right half (as the structure is usually drawn) resembles the nucleus of many of the substituted benzene-ring containing components found throughout the lichen world. Isolation of these products can give the raw materials that can be converted to the compound olivetol, a simple amyl-substituted resorcinol compound. 

The left half is a terpene which contains ten carbon atoms, and which is substantially identical to the essential oil, pulegone. This component makes up some 80 to 90% of the Oil of Pennyroyal.

The fusion of these two materials has been shown (Claussen et al., Tetrahedron Vol. 24 p. 2879 (1968)), to produce several products, one of which is delta-3-THC. This is a close structural isomer of delta-9-THC, the principal active component of marijuana, and is known to be active in man.

-- Dr. Shulgin

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