DELTA 1-TETRAHYDROCANNABINOL,*

A FAT-SOLUBLE "VITAMIN M" FROM MARIJUANA

Abstract. Delta 1-Tetracannabinol, delta 1-THC, the major active ingredient of marijuana, (1), has numerous physical, chemical, biochemical, metabolical and medical relationships with the fat-soluble vitamins. Two new metabolite formulas are presented. These relationships are close enough to suggest that delta 1-THC could also be a fat soluble vitamin! Delta 1-THC is herein named Vitamin M.

Marijuana, the flowering tops of female Cannabis sativa L., is known to contain a physiologically and psychologically active ruby-red oil that is not soluble in water, but is soluble in alcohols, ethers and other lipid solvents, (1). This active, ruby-red oil is different from most lipids in that it does not form soaps and is classified as a non-saponifiable lipid along with essential fragrances and flavors, fat-soluble vitamins, steroids and plant pigments, (2). This active, ruby-red oil is known to contain several major ingredients, including variable proportions of cannabidiol, CBD, delta 1-tetrahydrocannabinol, delta 1- THC, and cannabinol, CBN, (Fig.1)(1). The relatively inactive oil, CBD, is photosynthetically isomerized to the major active oil, delta 1-THC, and then the delta 1- THC is slowly oxidized to the relatively inactive oil, CBN, (Fig.1)(1). The high concentration of these oils in the female flowers suggests that they play an important role in the reproduction of the plant.

Fig. 1. The major oils of the active red oil of marijuana, (1).
Cannabidiol (CBD), Delta 1-Tetrahydrocannabinol (Delta 1-THC), Cannabinol (CBN)

Many of the properties of delta 1-THC are similar to those of the fat-soluble vitamins. These properties include the fact that the best known source of delta 1-THC, Cannabis sativa L., is one of man's oldest crops. It is man's oldest medicine and it's oil rich seeds are very rich in Vitamins E and K. The leaves are very rich in Vitamin A and the other leafy-green vegetable vitamins and minerals.

Table 1. Some properties of fat-soluble vitamins, (2), & delta 1-THC, (1).

Name___Vitamin___Source___Appearance___Formula____Use___Dose(mg/d)


Retinol_______A ____ Veg._____Clear oil_____C20H30O____Vision___2.4
Ergocalciferol__ D____Yeast____White xtls____ C27H41O____Bone____0.02
Tocopherol____E_____Wheat___Clear oil_____C29H50O2___Fertility___2.0?
Phytonadione__K_____Alfalfa___Clear oil______C31H46O2___Blood___2.0?
Delta 1-THC__M____Cannabis__Clear oil______C21H30O2___Nerves__2.0?

Not only are these properties of delta 1-THC similar to those of the fat-soluble vitamins, but also the chemical structure of delta 1-THC, (Fig.2), has a unique relationship with those of the fat-soluble vitamins, (Fig.2)(1&2). The chemical structure of vitamin A includes a beta-ionone moiety and a side chain of two isoprene units, (Fig.2)(2). The chemical structure of vitamin K includes a naphoquinone moiety and a side chain of four isoprene units,(Fig.2)(2). The chemical structure of vitamin E includes a benzopyran moiety and a side chain of three isoprene units, (Fig. 2)(2). The chemical structure of delta 1-THC includes a dibenzopyran moeity and a side chain of one isoprene unit, (Fig.2)(1). The chemical structure of vitamin D includes a steroid moiety, cyclopentanophenanthrene, and a side chain of one isoprene unit, (Fig.2)(2). The chemical structure of delta 1-THC fits the apparent sequence of fat-soluble vitamin structures between vitamins E and D and is most similar the chemical structures of vitamin E and K, (Fig.2).

Not only is the chemical structure of delta 1-THC related to those of the fat-soluble vitamins, but also the metabolites of delta 1-THC are analogous with the metabolites of vitamin A. Delta 1-THC is known to be metabolized to 7-hydroxy delta 1-THC by the liver soon after administration, (Fig.3)(3). This active alcohol group on 7-hydroxy delta 1-THC is known to be further metabolized to an aldehyde group, (Fig.4), and ultimately oxidized to a carboxyl group, (Fig.6), and excreted, (4). Vitamin A, an alcohol metabolite of carotenoid plant pigments, is known to be metabolized to an active aldehyde metabolite, retinene, by a dehydrogenase enzyme and nicotinamide adenine dinucleotide, NAD, and ultimately to a carboxyl metabolite, (2). Both metabolites conjugate to protein, but retinene is involved in the visual process and metabolism and the carboxyl metabolite is only involved in general metabolism, (2). The active alcohol metabolite of delta 1-THC, 7-hydroxy delta 1-THC, may be further metabolized to an active aldehyde metabolite, such as 7-formyl delta 1- THC, 7-HCO delta 1-THC, by NAD, analogous to retinene, (Fig.4). Some of this metabolite could conjugate to protein and may even transaminate to other active intermediate metabolites, such as 7-amine delta 1-THC, 7-NH2 delta 1-THC, (Fig.5). These metabolites are ultimately oxidized to the carboxyl metabolite, 7-carboxyl delta 1-THC, 7-COOH delta 1-THC, with an additional hydroxyl group on one of the first three carbons of the side chain, (Fig.6)(4). This metabolite occurs free, but most occurs conjugated to protein, (4). No glucuronides of delta 1-THC have been found, as have been found after administration of many harmful substances, (1). The activity of any carboxyl metabolite of delta 1-THC is still unknown, (4), but the carboxyl metabolites of vitamin A are active, (2).

Unfortunately, the exact metabolic roles of these metabolites of delta 1-THC are still unknown, as are the roles of any metabolite of vitamin E. Most animal studies of marijuana and delta 1-THC use large toxic doses that animals are averse to, rather than small daily doses that animals could benefit from, (5). The subtle physiological and psychological effects of delta 1-THC are analogous to those of the fat-soluble vitamins in that toxic doses are easily recognized compared to the difficulty of recognizing the very subtle and elusive biochemical effects of minimum daily requirements of the fat-soluble vitamins and delta 1-THC, (Table 1), and deficiencies. More research is needed to determine the effects of small doses of delta 1-THC on metabolism and growth, as was done with the vitamins. All that is known about deficiency effects is that no typical drug-withdrawal symptoms occur, (6). The relationship of marijuana and glaucoma suggests some parallel with vitamin A and vision.

The numerous therapeutic applications of marijuana suggest that it may help relieve many common symptoms such as poor appetite, nervous tension, headaches, minor pains, constipation, insomnia, mental depression, side effects and withdrawal symptoms of many drugs, aggression, anxiety and "The Blues", (6,7&8). Marijuana, if decriminalized and used properly, could alleviate an important part of the world's two major problems, malnutrition and suffering. It could also increase our freedom, brotherhood, happiness and consciousness!

Delta 1-Tetrahydrocannabinol, delta 1- THC, the major active ingredient of marijuana, (1), has numerous physical, chemical, biochemical, metabolical and medical relationships with the fat-soluble vitamins. These relationships are close enough to suggest that delta 1-THC could also be a fat-soluble vitamin, herein named Vitamin M.

Fig. 2.Chemical Structures of fat-soluble vitamins, (2), & delta 1-THC, (1).
Fig. 3.Metabolite 1 of delta 1-THC, 7-hydroxy delta 1-THC, (1,4).
Fig. 4.Metabolite 2 of delta 1-THC, 7-formyl delta 1-THC, (New).
Fig. 5.Metabolite 3 of delta 1-THC, 7-amine delta 1-THC, (New).
Fig. 6.Metabolite 4 of delta 1-THC, 2"hydroxy-7carboxy delta 1-THC, (4).

* Ed. Note: Old Numbering System, Delta 1-THC = New Numbering System, Delta 9-THC.

Ed. Note: Includes two new unpublished formulas! Both of which could probably be injected directly into the brain as can 7-hydroxy delta 1-THC. (for scientific purposes only).

See also Related Ubiquinone Formula. Not only is Ubiquinone (aka: CoQ10) similar to Phytonadione, Vitamin K, but also to the quinone derived from THC when THC is dissolved in 95%EtOH-KOH Solution (The Famous Purple Beam Test for THC).

References and Notes

  1. R. Mechoulam, Science 168, 1159 (1970) & 169, 611 (1970).
  2. I. Liener, Organic and Biological Chemistry, p. 48-52, 167, 421-431, Roland Press, N.Y. (1966).
  3. R. Foltz, A. Fentiman, Jr., E. Leighty, J. Walker, H. Draws, W. Schwartz, T. Page, Jr. E. Truitt, Jr., Science 168, 844 (1970). I. Nilsson, S. Argurell, J. Nilsson, A. Ohlsson, F. Sandberg, M. Wahlqvist, Science 168, 1228 (1970). H. Christensen, R. Freudenthal, J. Gidley, R. Rosenfeld, G. Boegli, L. Testino, D. Brine, C. Pitt, M. Wall, Science 172, 165 (1971). L. Lemberger, N. Tamarkin, J. Axelrod, I. Kopin, Science 173 72 (1971). L. Lemberger, R. Crabtree, H. Rowe, Science 177, 62 (1972).
  4. S. Burnstein, J. Rosenfeld, T. Wittstruck, Science 176, 423 (1972).
  5. T. Elsmore, G. Fletcher, Science 175, 911 (1972).
  6. A. Weil, N. Zinberg, J. Nelson, Science 162, 1234 (1968). L. Holister, Science 172, 21 (1971).
  7. R. Walton, Therapeutic Applications of Marijuana, reprinted in The Marijuana Papers, p. 447- 454, Signet Books, N.Y. (1966).
  8. F. Mikes, P. Waser, Science 172, 1158 (1970). M. Galanter, R. Wyatt, L. Lemberger, H. Weingartner, T. Vaughan, W. Roth, Science 176, 934 (1972).
  9. December 1972. (anonymous)

Clinical Endocannabinoid Deficiency Syndrome, 2004


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