Propyl Cannabinoids

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Before 1969 it was thought that all naturally occurring cannabinoids had the pentyl or five carbon side chain in the right hand (benzenoid) ring. Then some samples were discovered which contained small amounts of cannabinoids with a propyl or three carbon side chain instead of the pentyl. The three analogs of CBD, THC and CBN with the propyl side chain are termed cannabidivarol (CBDV), tetrahydrocannabivarol (THCV) and cannabivarol (CBV). Samples having significant amounts of these compounds generally come from India and adjacent areas (Nepal, Afghanistan, Pakistan), South Africa and Indonesia. However, it is assumed that further testing will reveal their presence in marijuana from other areas. Small quantities have been detected in marijuana from 29 countries; only seeds from Morocco, Poland and Turkey yielded plants without at least traces. As the table below shows, some samples may contain up to 50% of their cannabinoids as THCV or CBDV. Some South African plants have as high as 80% of the total cannabinoids present as THCV. It is presently unknown whether the quantity of these compounds is affected by age, sex or plant part in any way significantly different from that of the pentyl cannabinoids. The only relevant data, from South African plants grown indoors, are presented below. It is apparent that higher temperatures favor the production of propyl compounds relative to pentyl and of cannabinoids in the males relative to the females.

MALE FEMALE

THCV 0.14 0.08

THCV 0.02 0.06

(Plants grown from South African seeds indoors at 32° C or 22° C for 16-hour light period, then 12°C for eight-hour dark period.)

It is especially interesting that the duration of action of the propyl cannabinoids is significantly shorter than that of the pentyl compounds. Smoking marijuana with large amounts of THCV should produce a shorter high than usual, but human ex-

TABLE 8

Cannabinoids and Propyl Cannabinoids of High Potency Strains

All values are % of total cannabinoids rounded off to nearest % THCV « Tetrahydrocannabivarin CBDV = Cannabidivarin T = <1%

Marijuana o

SEED ORIGIN

GROWN IN

CONDITION

THC

THCV

CBD

CBDV

Afghanistan

USA (Mississippi)

Vegetative

48

T

Flowering

67

4

4

10

South Africa

France

Immature

70

17

-

-

South Africa

Indoors

Immature

65

30

South Africa

USA (Mississippi)

Flowering

-

54

T

India

USA (Mississippi)

Flowering

11

2

Nigeria

USA (Mississippi)

Vegetative

9

T

Indonesia

Indonesia

Flowering

81

-

3

T

Flowering

3

-

12

50

Flowering

31

-

14

20

Flowering

70

-

6

SEED ORIGIN

GROWN IN

CONDITION

THC

THCV

CBD

CBDV

Thailand (1971)

Norway

Immature

80

-

9

-

Thailand (1972)

Norway

Immature

89

-

8

-

Turkey (1971)

Norway

Flowering

3

-

96

-

Turkey (1972)

Norway

Flowering

13

85

South Africa

Norway

Immature

84

-

4

South Africa

South Africa

Flowering

56-92

-

3-12

-

Burma

Burma

Flowering

9-22

-

11-25

-

Nigeria

Nigeria

Flowering

26-78

-

4-13

-

Jamaica

Jamaica

Flowering

55-98

-

2-17

-

Morocco

Morocco

Flowering

45-66

-

30-40

-

Hashish

SEED ORIGIN

GROWN IN

CONDITION

THC

THCV

CBD

CBDV

Nepal

Nepal

Flowering

3-12

2-6

36-41

9-12

Pakistan

Pakistan

Flowering

15-53

-

39-57

-

Lebanon

Lebanon

Flowering

25-36

-

59-66

-

Afghanistan

Afghanistan

Flowering

42-61

-

35-45

-

SOURCE: R.W. Jenkins and D.A. Patterson, "The Relationship Between Chemical Composition and Geographical Origin of Cannabis," Forensic Science 2 (1973): 59; C.E. Turner et al., "Constituents of Cannabis sativa L. VI," Journal of Pharmaceutical Science 62 (1973): 1739; Mobarak etal., "Studies on Non-Cannabinoids of Hashish. II," Chemosphere 3 (1974): 266; C.E. Turner and K.W. Hadley, "Chemical Analysis of Cannabis sativa of Distinct Origin," Archivos Investigación Medica 5, supplement (1974): 144; M. Paris et al., "Importance des Composes Propyliques dans le Cannabis Originaire d'Afrique du Sud," Plantes Medicinales Phytotherapie 9 (1975): 136; K.H. Davis et al., "The Preparation and Analysis of Enriched and Pure Canna-binoids from Marihuana and Hashish," Lloydia 33 (1970): 453; F. Merkus, "Canna-bivarin and Tetrahydrocannabivarin, Two Constituents of Hashish," Nature 232 (1972): 579; P.S. Fetterman etal., "Mississippi Grown Cannabis sativa L.," Journal of Pharmaceutical Science 60 (1971): 1246; P. Chambón et al.. "Problemes Poses Par la Culture Locale du Chanvre et Dosage des Chanvre," Bulletin des Traveaux de la Societe de Pharmacia de Lyon 16 (1972): 46.

periments have not yet been reported. For further discussion of chain length and chemical syntheses, sec the chemistry section of this book.

Cannabinoid Content of Female Flowering Tops

It is well known that marijuana from various areas of the world varies considerably in potency, but only very recently has any quantitative data become available. Table 8 gives figures in percent of dry weight for the CBD and THC contents of female flowering tops. The high THC strains are generally found south of latitude 30° North, although there are many exceptions to this. For example, one of the wild Illinois strains contained 2.3% THC. Most wild American hemp has derived from plants that were grown for fiber, and often originated from seeds imported from China in the nineteenth century. Though most Chinese strains are probably of the high THC type, natural selection eventually changed these into the high CBD, low THC type. It should be kept in mind that the figures presented are by no means exhaustive of the range of variation existing in each country, and that in many cases much higher contents would be found if more extensive studies on completely mature plants were done. Also, the recent development of an extensive underground traffic in marijuana has led to seeds of diverse origins being deliberately cultivated or scattered about in nearly every country, so we never know for certain (especially for wild stands) whether the particular plants studies derive from numerous inbred generations or if they are the result of a recent cross with seeds from the other side of the world. Nevertheless, Mississippi researchers found a five-fold variation in THC content of plants derived from seeds from a single plant and, undoubtedly, such variation is neither uncommon nor the maximum. It is likewise reasonable to expect more variation in the offspring if the parents are of different strains.

In spite of these difficulties, the data are probably quite typical for plants from the areas indicated. It should be useful to refer to the section on cannabinoid phenotypes before studying table 8.

One point of immediate interest is the extreme variation in potency of samples from one country. The study on Argentinian plants showed a range of 0.5 to 8.3% THC; that is, from very weak to a quality comparable to the best Colombian or Thai marijuana. Mexican marijuana seized at the border was tested and found to be quite weak. Of 40 batches seized, only ten of them had greater than 1% THC, and the range was 0.7 to 2.87%. Evidently there are still hundreds of tons of Mexican weed being imported which are quite incapable of getting anyone stoned. Presumably they are being bought by teenagers who can't tell the difference between grass and oregano. Even the best of the Mexican marijuana tested was still only half as potent as good Colombian, Jamaican or Thai and, furthermore, had the additional disadvantage of higher CBD content than the latter types. A series of samples analyzed in Jamaica averaged 2.96% THC with a range of 0.7 to 10.3%, the latter figure being the equal of the most potent marijuana grown anywhere. Ten Costa Rican samples varied from 1.0 to 3.7%. Similar variation is observed in the plants of the high CBD type, as in wild Illinois marijuana where the CBD ranges from traces to more than 7%.

There is much speculation as to the maximum potency obtainable from marijuana. THC contents over 8% are seldom found, except for a few unpublished studies which claim ranges up to 15%. Values over 10% must be regarded with suspicion, since there is the possibility that hash oil may have been added. This is especially true of hashish. Sampling error is another serious problem, if a small amount chosen for analysis contains mostly flowers or bractlets, very high values might be obtained, but these would not be truly representative of the whole flowering top. Likewise, samples may be biased toward lower values. To avoid this problem, a thoroughly mixed sample of some two to four grams of material should be extracted and analyzed. It is possible that breeding programs may be able to increase potency beyond that which occurs in nature.

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  • margaret lucas
    What is a propyl cannabinoid?
    9 months ago

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