Alphora Research Inc.

Navindra Jainarine Ramjit

Jason Edward Field

Boris Gorin

Fabio E S Souza

Jan Oudenes

Ming Pan

Ricardo Orprecio

Fabio Eduardo Silva E Souza

Tracey Jende-Tindall

Emma-Louise Moore

Tharsika Tharmanathan

Dronabinol, the tetrahydrocannabinol compound which comprises the active constituent of marijuana and is pharmaceutically useful as an antiemetic, is prepared by a process involving reaction of cis-menth-1-enc-3,8-diol with olivetol to form 1,3-dihydroxy-2-[(1R,6R)-6-(2-hydroxyprop-2-yl)-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene; and cyclizing the 1,3-dihydroxy-2-[(1R,6R)-6-(2-hydroxyprop-2-yl)-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene so formed to obtain dronabinol. A novel synthesis of cis-menth-1-ene-3,8-diol is also provided.

Synthetic route to dronabinol

An individual tetrahydrocannabinol isomer of interest is separated from a mixture containing two or more such isomers, by treating the mixture with an isocyanate or isothiocyanate of formula I:R&#x2014;(CH)&#x2014;N&#x2550;C&#x2550;X&#x2003;&#x2003;(I)where R represents an aromatic ring optionally substituted with one or more electron withdrawing groups, n=0 or 1 and X is oxygen or sulphur; so as to produce a crystallizable THC carbamate of formula II: wherein X and R are as defined above, R' is a C-Calkyl group and the dotted lines indicate optional unsaturation including aromatic, separating the compound of formula II from solution in isolation of other THC derivatives, and hydrolyzing the compound of formula II to form the individual tetrahydrocannabinol isomer of interest.

Separation of tetrahydrocannabinols

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Navindra Jainarine Ramjit