Synthesis of 11-nor-.DELTA.-9-tetrahydrocannabinol-9-carboxylic

Details Synthesis of 11-nor-.DELTA.-9-tetrahydrocannabinol-9-carboxylic Synthesis of 11-nor-.DELTA.-9-tetrahydrocannabinol-9-carboxylic

1991-11-27

1994-03-08

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549396, C07D31180, C07D31100

Patent

active

052928993

ABSTRACT:
A method of producing a deuterated or undeuterated 11-nor-.DELTA..sup.8 -tetrahydrocannabinol (THC) glucuronide or deuterated or undeuterated 11-nor-.DELTA..sup.9 -THC glucuronide by reacting a blocked THC carboxylic acid precursor with a blocked sugar epoxide precursor is disclosed. Also disclosed are: deuterated 11-nor-.DELTA..sup.8 - or .DELTA..sup.9 -THC carboxylic acid glucuronide having a deuterated hydrocarbon chain; 5'-deuterated 11-nor-.DELTA..sup.8 - or .DELTA..sup.9 -THC-carboxylic acid or 5'-deuterated .DELTA..sup.8 - or .DELTA..sup.9 -THC glucuronide. The compositions are useful as GC-MS standards; in methods for preparing antibodies reactive with a THC glucuronide; and, in GC-MS diagnostic methods for THC metabolites.

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