University of the Pacific Scholarly Commons Thomas J. Long School of Pharmacy and Health Pacific nforI mation Service on Street-Drugs Sciences

3-1-1973 Pacific nforI mation Service on Street-Drugs March 1973 School of Pharmacy

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NO. 3 14

Tab 1e 1 - Structures of Cannabi noi ds from sativa L.

R R·1

Cannabinoid R-1 Other

1::.9,10 1::.9-Tetrahydrocannabi no 1 C5Hll 69-Tetrahydrocannabi orco 1 CH ~::.9·10 3 1::.9,10 69_ Tetrahydrocannabi va ri n Cb 69-Tetrahydrocannabi vari ni c Acid COOH C3H7 1::.9,10 1::.9 ,1 0 69-Tetrahydrocannabino lic Acid COOH C5H11 8 1::.8,9 6 -Tetrahydrocannabi no 1 C5H11 IJ.6a,7;1J.8,9;1J.10,10fJ. C5H11 C3H7 IJ.6r:J.7;1::.8,9;1J.10 ,10 a Cannabiorcol CH IJ.6a ,7;ti.8,9;1J. 10,10 a 3 IJ.6a7;1J.8 ,9;1J.10 ,1 0a Cannabi no 1i c Acid COOH C5H11

10

Cannabi noi d R-1 R-2 Other

61, 2; 8,9 OH C5Hll 6 OH C5Hll 61, 2;68,9 Cannabidiol ic acid OH COOH C5Hll 61,2;1::.8 ,9

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Cannabi noi d (cant.) R-1 R- 2 Other

H ll l,2 ;ll8 , 9 Cannabidiol monomethyl ether OCH 3 C5Hl l COOH ll l,2 ;ll8 , 9 Cannabi di o1 i c Acid monomethy l ether OCH 3 C5Hll · Cannabidivarin OH C3H7 ll l,2 ;ll8 ,9 CH COOH ll l,2 ;ll8 ,9 Cannabidivarinic Acid 3 C3H7 ll l,2 ;ll8 ,9 Cannabi di orca 1 OH CH 3

Cannabi e 1soi c Acid OH /" I R 1 R::-..., 10"

Cannabinoid R-1 R-2 Other OCH ll l,2 ;ll4 , 8 Cannabi gero 1 monomethyl ether 3 C5Hll ll l,2 ;ll4 , 8 OH COOH C5Hll COOH ll l,2 ;ll4 , 8 Cannabi gero 1i c Acid monomethyl ether OCH 3 C5Hll Cannabidiolic Acid Tetrahydrocannabitriol Ester

Cannabi noi d Cannabinoid R-1

Cannabi chromene (Cannabipinol) Cannabi chromeni c Acid COOH Cannabi eye 1o 1 i c Acid

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Marihuana is an aphrodisiac, it produces organic brain damage, facili­ our 1ack of definitive knowledge of how altered phys i co-bi ochemi ca 1 reactions tates creative thinking, induces respiratory disorders, is toxic to the li~er, affect motivations and emotions and vice-versa: particularly when, in contrast, euphoric, di starts the senses, dtl ates the pupil wit~ reddening of the conJ unc­ knowledge of the biochemical mechanisms regulating, say cardiac function, tival sac, increases heart rate, s1~ells the uvula, d1sturbs motor control, is progressing reasonably well. sensitizes skin to acne, precipitates paranoia, etc. These are some of the terms used in the claims and counterclaims of today's emotional drug mael­ · In spite of dramatic claims to the contrary (23,26,27), no well-designed strom fomented by almost daily articles in lay and pseudoscientific publica­ experimenta 1 data exist showing that marihuana (or THC) produces organic brain tions: As should have been learned from experiences with earlier "miracle damage, although considerable evidence is accumulating that marihuana may drugs" (penicillin, krebiozen, DMSO) subjective op~nions c~n only confou~d, produce more psychic and physi ca 1 depress ions than users acknm1l edge (20 ,28-30) . not resolve, controversy. Relatively few wel1-des1gned ammal and espec1ally Attention span is reduced, brief loss of memory may occur, as 11ell as possibly clinical experiments have been performed with marihuana or h~shish. Unfortu­ a decreased rate of 1earning. The user has an inflated opinion of his menta 1 nately, 1ay impatience, spurred on by overly-zealous .J?u~na l1sm an~ TV, has. and physical capaliil ities, which in combination with poorer critical judge­ not provided enough Ume in wlii ch to perform the def1 m ~1 ve object1 ve expen­ ments plus modest hallucinations, particularly 11ith lights and sounds, and ments needed so badly. This does not mean that conclus1ons cannot n?w be some reduced motor performance, makes for a potentially hazardous car driver: drawn but, in many cases, such conclusions .are, at be~t, only tentat1ve, a problem of major concern and many mixed opinions (3,20,21). Most opinions pending the results of more and better des1gned expenments. seem to support the view that marihuana induced impaired driver performance may be a contributing factor in automobile accidents, although the exact Controversy exists as to whether marihuana is a "true" aphrodisiac (i.e. nature and degree of marihuana effect is still the subject of much controverisal induces increased libido) or whether it exhibits a sedative or anti-anxiety experimentation involving questionable simulated methodology short of actual ("disinhibitory") effect, more similar to that of alcohol. However, little street driving tests. Resolution of this controversy should be forthcoming, argument can be made with the c1 aim that marihuana. enhances se~ua 1 p1 easure since much pressure is being applied to political, legislative and health in a manner more satisfying than alcohol, amphetam1nes or coca1ne - usually officials. considered the more sexually stimulating of drugs (2,20-23). The enhance- ment appears to be due in part to a "disinhi~itory" effect, simila~ to .moderate It is interesting to note that all of the psychic responses to marihuana sedative doses of alcohol. In addition, manhuana appears to prov1de 1n- . . listed in Table 2 can be explained on the basis of a disinhibitory (or sedative) creased sensory awareness: co 1or, sound and texture as well as other moda l1 t1 es activity. Many investigators regard the mild hallucinations as being more appear to be enhanced with the use of marihuana. Feelings of general body a state of brief euphoria resulting from removal of inhibitions and anxiety warmth, brotherhood, empathy and oneness with. oth~rs (a 1so common responses to feelings, and therefore more similar to alcohol depression, than LSD hallu­ alcohol use) are sensations reported as contnbut1n~ to more ple~surable cinations. Increased sensual awareness may be the consequence of removal of sexua 1 re 1ati onships. However, the genera 1 and gem ta 1 anesthes1a reported competitive centra 1 nervous activity ( i . e. decreased cerebra 1 thought processes with alcohol, resulting in reduced performance, is not nearly .as :req~ent an and peri phera 1 motor activity) thereby permitting greater numbers of extern a1 occurrence with marihuana, pro vi ding i ndivi dua 1 1eve 1 of i ntox1 cat10n 1s sensory stimuli to be received and responded to centrally. titrated by the number of inhalat1'ons or "tokes" in a manner analogous to drinks of alcohol. The disinhibitory effect seems to produce a degree of Another psychic consequence of chronic marihuana usage is a tendency to brief euphoria and certainly relief from anxiety (22). decrease long-range planning and "live for today". As a consequence, edu­ cational and occupational goals become of secondary importance with a cor­ One of the more s i gni fi cant findings has been the number of chronic responding increase in schoo 1 and work i neffi ci ency and absenteeism, and marihuana smokers who have developed tolerance to marihuana, as evidenced by eventually rejection by their peer groups (3,21 ,26). These drop-outs must requiring 100 or more grams of marihuana per m?nth. (24). This is ~n agree­ then find ne1~ 11ays for receiving soci a1 acceptance and persona 1 i dentifi cation. ment with earlier reports of tolerance develop1ng 1n m1ce, ~a~s, p1geons, Thus they seek out a new peer group 1·1ith similar problems and frequently in­ chicks and monkeys (25). Physical withdrawal syndromes to 1n~ected THC . volving drugs as part of the solution to their daily problems. Here then is have been reported for pigeons and monkeys but, to date, not 1n man. Th~s the central point of this controversy. Society calls such a marihuana peer question may be answered soon if the current European trend to use the flVe group (drug culture) as being non-productive for society in spite of the peer to ten times more potent occurs in the U.S. as expected (24). group's claim to greater intellectual creativity. The marihuana peer group states that because of the lowered tensions, increased sensual awareness and Often times the drug user miscontrues the psychic responses (i.e. stimulated intellectual creativity, each person now becomes more productive ha 11 uci nations, ~ensua 1 alterness, judgements, etc.) as being caused by individually and thus can now contribute to that particular drug culture. mechanisms entirely different from those precipitating physical responses. Resolution of this intellectual dichotomy will be helped more by philosophical Psychic and physical responses to drugs are the result of drug:ind~ced altera­ and political facts than by pharmacological data. tions in physico-biochemical body reactions. T? assume othenme 1s cont~ar~ to long established physiologic and pharmacolog1c knowledge and fosters w1th1n Scattered throughout the 1iterature are numerous suggestions that smok ­ the user a false sense of security that a drug-induced psychic response is ing marihuana produces, in addition to many behavioral and psychological not as serious as a drug-induced change, say in heart rate or blood pressure. effects, certain physi ca 1 effects-perhaps the most notab 1e being respiratory One of the major differences between psychic and physical drug responses is

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19 disorders such as bronchiti s, asthma and oropharyngitis (3,21 ,24). Bronchial complaints are chiefly bronchitis 1·1ith dyspnea, productive cough, rales and wheezing . Chest X-rays and sputum cultures are essentially normal. The Table 2 - Human Responses to Smoked Marihuana patients are frequently disabled to the point of being unable to ~10rk and may occasionally require hospita 1i za ti on. Antibiotic therapy does not he 1p. Only a decrease in marihuana consunpti on has appreciably improved their Parameter Response respiratory symptoms ( 24) . Habituation Yes X-rays reveal sinus congestion in hearly all cases, although pain is Tolerance Maybe minima 1. Antibiotics with nasal decongestants usually reso 1ve the rhino­ Psychic dependence pharyngitis, altho11gh continued smoking brought reoccurrence as does renewed Phys i ca 1 dependence ~~rf smoking in marihuana-induced bronchitis and asthmatic attacks. Uvular edema, a common concurrence with marihuana-induced bronchitis and/or rhi nopharyngi tis, Psychic: can be a useful diagnostic sign, more reliable than cardiac or conjunctival Hallucinations Mild signs of a marihuana smoker (24). Euphoria Brief Toxic psychoses No* t·1any young chronic marihuana smokers develop acne and seborrheic dermatiti s , Sensua 1 Awareness Increased but it is difficult to relate these entities specifically to marihuana, as Learning rate Decreased poor personal hygiene in drug users may be as responsible as THC (32). Memory Brief loss Attention span Shortened Diarrhea, ab dominal cramps and emesis have been observed in laboratory Judgement Poor animals as well as in humans smoking or receiving intravenous marihuana prod­ Long-range planning Decreased ucts. \~eight loss usually accompanies the above noted gastrointestinal com­ Self-opinions Inflated plaints (24). Flashbacks No* Physical: Marihuana smoking, particularly by subjects without previous experience, EEG activity Slowed causes an increased heart rate and an increase in peripheral blood flow Sedation Yes through arms and 1egs due to dilatation of the b1 ood vesse 1s. The vasodil a­ Analgesia Maybe* tation results in sufficient blood flow through the skin to result in a drop Blood pressure Increased in body temperature through skin heat loss--a definite hazard to scuba divers, Heart rate Increased skiers or any person 1vho spends time outdoors in a cool or cold environment. Respiratory rate Normal Sti 11 another similarity between marihuana and ethanol activities. The Respiratory depth Irregular currently accepted mec hanism for this cardiovascular response necessitates Rales Yes considerable caution in the concurrent administration of va soactive drugs Uvula Swollen such as amyl nitrite or anesthetics like ethers and alcohol to tho se persons Mouth Dry who may have been smoking marihuana (20,33-38). The field of drug interactions Nausea, anorexia Yes with marihuana is just beginning to be explored, but the potential list of Body weight Loss interactions is every bit as large as the known drug interactions \'lith alcohol. Emesis Maybe* Herein 1i es perhaps the greatest potentia 1 hazard of marihuana today: inter­ Gastrointestinal motility Increased actions with other drugs-a hazard aggrevated by the lack of much experimental Diarrhea Yes activity at this time. Pupillary size Increased Conjunctiva 1 vesse 1s Dilated Body temperature Reduced Ralph vi. Morris, Ph. D. Motor activity Reduced Professor of Pharmacology, and Motor performance Poor Norman R. Farnsworth, Ph.D. Blood levels Normal Professor of Pharmacognosy Hepatotoxicity No College of Pharmacy University of Illinois at the Medical Center Chicago, Illinois 60612 NOTE: * = controvers i a1

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BIBLIOGRAPHY

1. Gamage,J.R . and E.L.Zerkin. 1969. A oomprehensive guide to the English­ language literature on Cannabis (marihuana }. Stash Press, Beloit, Hisconsin. 2. Wa11er,C . and J.L.Denny. 1971. Annotated bibliography of marihuana (Cannabi s sativa L. J l964 - l970 . Res .lnst.Pharm .Sci., School of Pharmacy, University , Mississippi. 3. Anon. 1972. Marihuana: a signal of misunderstanding. First Report of the Nation a1 Commission on Marihuana and Drug Abuse, Washington, D.C. 4. Ho11ister,L. 1971 . Marihuana fn man: three years later. Soienoe . 172:21. 5. Harris,L.S. 1971. General and behavioral pharmacology of marihuana . Pharmaool .Rev . 23:285 . 6. Wa11er,C.W. 1971. Chemistry of marihuana. Pharmaool .Rev . 23:265 . 7. Newmeyer,J.L. and R.A.Shagoury . 1971. Chemistry and pharmacology of marihuana. J.Pharm.Soi . 60:14 33 . 8. Pillard,R.C . 1970. Marihuana. New Engl.J.Med . 283:294. 9. Anon. 1970. A review of the biomedioal effeots of marihuana in the military environment . Life Sci .Res.Off., Federation of Amer.Soc.E xptl.Biol., Bethesda, Maryland. 10 . Joyce,C.R.B. and S.H.Curry (Eds .). 1970. The botany and ohemistry of Cannabis . J & A Churchi 11 , London. 11. Mechoulam,R. et al. 1970. Chemical basis of hashish activity. Soienoe . 169:611. 12. Mechoulam,R. 1970. Marihuana chemistry. Soienoe. 168: 1159. 13. Mechoulam,R . 1970. Developments in hashish research. Harokeaoh Hawri . 13:535. 14. Farnsworth,N.R. 1969. Pharmacognosy and chemistry of . J.Amer .Pharm.Assoo. NS9:410. 15. Agure11,S.L. and I.M.Nilsson. 1969. Cannabis-chemistry, biochemistry and pharmacology. Mod .Kemi. 1969(11): 30. 16 . Slatkin,D.J. et al. 1971. Chemical constituents of Cannabis sativa L. root . J.Pharm.Soi. 60:1 891. 17. Klein,F.K . and H.Rappoport . 1971. Cannabis alka loids. Nature . 232:258. 18. Ohlsson,A. et al. 1971. Cannabinoid constituents of male and female Cannabis sativa. BuU .Narootios 23:29. 19. Fetterman,P .S . et al. 1971. Mis sissippi-grown Cannabis sativa L. Pre­ limina ry observation on chemical definition of phenotype and variations in content versus age, sex, and plant part. J.Pharm . Soi . 60:1246. 20. Weil ,A.T. et al. 1968. Clinical and psychological effects of marihuana in man. Soienoe . 162 :1234 . 21. Anon. 1971 . The drug orisis : report on drug abuse in Illinois. Illinois Legislative Commission. Springfield, Illinois. 22. Gay,G.R. and C.W.Sheppard. 1972. Sex in the drug culture. Me dioal Aspeots of Hwnan Sexuality . 28-50. 23. Kolansky,H . and W.T .Moore. 1972. To xic effects of chronic marihuana use. JAMA. 1: 35-41. 24. Tennant,F.S. et al. 1971. Medical manifestations as sociated with ha shish. JAMA. 12:1965-69. 25. Abel ,E.S. et al . 1972. Tolerance to the behavioral and hypothermic effects of delta-9 tetrahydrocannabinol in neonatal chicks. Experientia . 28(10) :11 88. 26. Kornhaber,A. 1971. Marihuana in an adolescent psychiatric outpatient population . JAMA. 215(12) :1988 .

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