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anhydrocannabisativine, and other alkaloids in cannabis.

Migrated topic.
Marijuana's active constituents contain no nitrogen and thus are not alkaloids, the cannabinoids produced by the marijuana plant are terpenoid hydrocarbons.

Yet alkaloids have been identified and do exist in cannabis plants...

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The first Cannabis alkaloid to be fully identified was cannabisativine which was isolated in Mississippi in 1975 from the roots of a Mexican variant (Lotter et al., 1975). TLC indicated the presence of this substance in the leaves of the plant as well. "

Article: Historical overview of chemical research on cannabinoids
·Raphael Mechoulam
·L Hanus

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So it caught my attention when I read of "anhydrocannabisativine" an alkaloid produced by a variant of the cannabis sativa plant.

Cannabimine A, may be identical to anhydrocannabisativine, which shares the same molecular formula (-bottom of page)

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Abstract
Ethanol extracts of the leaves and roots of a Mexican variant of Cannabis sativa L. (marijuana) afforded, after partitioning and chromatography, the new spermidine alkaloid, anhydrocannabisativine. The structure was determined by spectral analysis and semisynthesis.


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Though further information regarding anhydrocannabisativine is sparse...

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For many years during the 19th century the possible presence of alkaloids was discussed. Preobrajensky (1876) claimed the presence of nicotine in Cannabis sativa resin but this was refuted by Kennedy (1886). Hay (1883) was able to obtain an alkaloid, tetanocannabin, which pos-sessed strychnine like properties when tested on a frog. Although the balance of evidence was in favor of some alkaloidal substance (in addition tocholine and trigonellin) being present in small quantity in Indian hemp, almost no further work along these lines was undertaken.This lack of data apparently did not prevent the marketing of ‘Cannabine Alkaloid Merck’ (MerckIndex, 1896), as ‘fine needles ... hypnotic without dangerous secondary effects’.The first solid indication of the presence of alkaloids in Cannabis, in addition to the above-described simple nitrogenous bases, was put for-ward much later in Klein et al. (1971). Alkaloidal mixtures were extracted from plant material. The total crude yield was 0.02%. Four alkaloids, named cannabimines A – D, were isolated bypreparative TLC. High-resolution mass spectro-metric data indicated molecular weights of 279 –363. Structural assignments could not be made.No further work on these alkaloids has been reported. Cannabimine A, C21H37N3O2 may be identical to anhydrocannabisativine, which sharesthe same molecular formula.The firstCannabisalkaloid to be fully identifiedwas cannabisativine which was isolated in Missis-sippi in 1975 from the roots of a Mexican variant(Lotter et al., 1975). TLC indicated the presenceof this substance in the leaves of the plant as well.The structure of cannabisativine was elucidatedby X-ray crystallography. A second alkaloid,named anhydrocannabisativine, was isolated in aminiscule yield by the same group from the leavesand roots of a Mexican variant ofCannabis sati6a(ElSohly and Turner, 1976). Anhydrocannabis-tivine has been found in plant samples ofCan-nabisfrom 15 different geographical locations.Several related spermidine alkaloids palustrineand palustridine (both found inEquisetumspe-cies) are known in nature.While the crude alkaloidal mixture caused de-creased activity in mice, in view of the low con-centration of the alkaloids in the plant, it isdoubtful whether these components are relevant to Cannabis activity in man. For a detailed reviewof cannabinoid alkaloids see Mechoulam (1988 )


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-eg
 
"Cannabinoids"

Caryophyllene CBC CBCV CBD CBDV CBG CBGM CBGV CBL CBN CBV Epigallocatechin gallate Gallocatechol Perrottetinene Serinolamide A THC THC-C4 THCA THCV Yangonin, 8,11-DiOH-THC 11-COOH-THC 11-OH-THC, Arachidonoyl ethanolamide (Anandamide or AEA) 2-Arachidonoylglycerol (2-AG) 2-Arachidonyl glyceryl ether (noladin ether) N-Arachidonoyl dopamine (NADA) Oleamide RVD-Hpα Virodhamine, A-40174 A-41988 A-42574 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-926 AM-938 AM-2389 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol (HU-211) DMHP Dronabinol HHC HU-210 HU-243 JWH-051 JWH-133 JWH-139 JWH-161 JWH-229 JWH-359 KM-233 L-759,633 L-759,656 Levonantradol (CP 50,5561) Menabitan Nabazenil Nabidrox (Canbisol) Nabilone Nabitan Naboctate O-224 O-581 O-774 O-806 O-823 O-1057 O-1125 O-1191 O-1238 O-2048 O-2113 O-2365 O-2372 O-2373 O-2383 O-2426 O-2484 O-2545 O-2694 O-2715 O-2716 O-3223 O-3226 Parahexyl Pirnabine THC-O-acetate THC-O-phosphate Cannabicyclohexanol CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 HU-308 HU-320 HU-331 HU-336 HU-345 HU-910 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1871 SPA-229 Tinabinol 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

"Benzoindoles"
1-Butyl-3-(2-methoxybenzoyl)indole 1-Butyl-3-(4-methoxybenzoyl)indole 1-Pentyl-3-(2-methoxybenzoyl)indole AM-630 AM-679 AM-694 AM-1241 AM-2233 GW-405,833 (L-768,242) Pravadoline RCS-4 WIN 54,461

"Naphthoylindoles"
AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 EAM-2201 JWH-007 JWH-015 JWH-018 JWH-019 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-164 JWH-182 JWH-193 JWH-198 JWH-200 JWH-210 JWH-398 JWH-424 MAM-2201 WIN 55,212-2

"Naphthylmethylindoles"
JWH-175 JWH-184 JWH-185 JWH-192 JWH-194 JWH-195 JWH-196 JWH-197 JWH-199

"Phenylacetylindoles"
Cannabipiperidiethanone JWH-167 JWH-203 JWH-249 JWH-250 JWH-251 JWH-302 RCS-8
JWH-030 JWH-147 JWH-307 JWH-369 JWH-370, AM-883 AM-1346 ACEA ACPA Methanandamide (AM356) O-585 O-689 O-1812 O-1860 O-1861 4-HTMPIPO 5-Fluoropentyl-3-pyridinoylindole 5F-PB-22 A-796,260 A-834,735 A-836,339 A-955,840 Abnormal cannabidiol AB-001 AB-FUBINACA AB-PINACA ADB-FUBINACA ADBICA AM-1248 AM-1714 APINACA AZ-11713908 BAY 38-7271 BAY 59-3074 CB-13 CB-86 CBS-0550 GW-842,166X JWH-176 JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-7 MDA-19 NESS-040C5 NMP-7 O-889 O-1269 O-1270 O-1399 O-1602 O-2220 Org 28312 Org 28611 PF-03550096 PSB-SB-1202 QUCHIC QUPIC S-444,823 SDB-001 (2NE1) SDB-006 SER-601 STS-135 Tedalinab UR-12 (MN-25) UR-144 URB-447 VSN-16 WIN 56,098 XLR-11 Org 27569 Org 27759 Org 29647 RTI-371

"Endocannabinoid
activity enhancers"
4-Nonylphenylboronic acid AM-404 Arachidonoyl serotonin Arvanil Biochanin A CAY-10401 CAY-10429 Genistein IDFP JNJ 1661010 JZL184 JZL195 Kaempferol LY-2183240 O-1624 O-2093 Oleoylethanolamide (OEA) Olvanil Palmitoylethanolamide (PEA) PF-04457845 PF-622 PF-750 PF-3845 PHOP URB-447 URB-597 URB-602 URB-754 VDM-11

"Cannabinoid
receptor
antagonists and
inverse agonists"
AM-251 AM-281 AM-630 AM-1387 AM-4113 AM-6527 AM-6545 BML-190 CAY-10508 CB-25 CB-52 CB-86 Drinabant (AVE1625) Hemopressin Ibipinabant (SLV319) JTE-907 LH-21 LY-320,135 MDA-77 MJ-15 MK-9470 NESS-0327 NIDA-41020 O-606 O-1184 O-1248 O-1918 O-2050 O-2654 Otenabant (CP-945,598 ) PF-514273 PipISB PSB-SB-487 Rimonabant (SR141716) Rosonabant (E-6776) SR-144,528 Surinabant (SR147778 ) Taranabant (MK-0364) TM-38837 VCHSR

(Great information regarding cannabinoids in the link above, an invaluable resource, plentiful accurate scientific information regarding cannabinoids and related topics)

-eg
 
Still doing research involving cannabis, but I'm about to call it quits and return to tryptamines, phenethylamines, and lysergamides. These hydrocarbon terpenoid compounds (and diterpenoid hydrocarbons in salvia divinorum) are very interesting, and much fun to research, very unique in terms of plant psychoactives, which are almost always alkaloids, which is an upside and a downside when researching these compounds

(Information in regards to "alkaloids in cannabis" )

1.1.Alkaloids For many years during the 19th century thepossible presence of alkaloids was discussed. Preobrajensky (1876) claimed the presence ofnicotine in Cannabis sativa resin but this was refuted by Kennedy (1886). Hay (1883) was able to obtain an alkaloid, tetanocannabin, which pos-sessed strychnine like properties when tested on a frog. Although the balance of evidence was in favor of some alkaloidal substance (in addition to choline and trigonellin) being present in small quantity in Indian hemp, almost no further workalong these lines was undertaken.
This lack of data apparently did not prevent the marketing of ‘Cannabine Alkaloid Merck’ (MerckIndex, 1896), as ‘fine needles ... hypnotic without dangerous secondary effects’.The first solid indication of the presence of alkaloids in Cannabis, in addition to the above-described simple nitrogenous bases, was put for-ward much later in Klein et al. (1971). Alkaloidalmixtures were extracted from plant material. Thetotal crude yield was 0.02%. Four alkaloids,named cannabimines A – D, were isolated bypreparative TLC. High-resolution mass spectro-metric data indicated molecular weights of 279 –363. Structural assignments could not be made.No further work on these alkaloids has beenreported. Cannabimine A, C21H37N3O2may beidentical to anhydrocannabisativine, which sharesthe same molecular formula.The firstCannabisalkaloid to be fully identifiedwas cannabisativine which was isolated in Missis-sippi in 1975 from the roots of a Mexican variant(Lotter et al., 1975). TLC indicated the presenceof this substance in the leaves of the plant as well.The structure of cannabisativine was elucidatedby X-ray crystallography. A second alkaloid,named anhydrocannabisativine, was isolated in aminiscule yield by the same group from the leavesand roots of a Mexican variant ofCannabis sati6a(ElSohly and Turner, 1976). Anhydrocannabis-tivine has been found in plant samples ofCan-nabisfrom 15 different geographical locations.Several related spermidine alkaloids palustrineand palustridine (both found inEquisetumspe-cies) are known in nature.While the crude alkaloidal mixture caused de-creased activity in mice, in view of the low con-centration of the alkaloids in the plant, it isdoubtful whether these components are relevanttoCannabisactivity in man. For a detailed reviewof cannabinoid alkaloids see Mechoulam (1988 )
(Bottom left of page two)

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While researching terpenes from plant sources other than cannabis, as well as their structural relationship to cannabis produced compounds, I would frequently recall shulgin talking about producing THC from "lichen and pennyroyal", it's a pulgone/olivetol condensation reaction in which he is describing, and regardless of the practicality of the notion I always found it am using.

In the below section shulgin discusses using a terpene compound derived from pennyroyal (pulgone) in a condensation reaction with benzene compounds derived from lichens (olivetol), to give delta-3-THC.

(Similar methods for production of delta-9-THC also exist)

(The "delta-9" is referring to the double bond (C=C) in the top right-hand section of ring C of the THC molecule, this double bond can occur in positions all around ring C... so "delta-3" suggest the double bond in ring C is in position number three, "delta-9" suggest the double bond is in position 9 of ring C. Each of these positional isomers of THC has distinst activity, pharmacology, and legal status)

Ok, now for shulgins comments: (under the line in the below section)

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The tetrahydrocannabinol molecule from Cannabis can be viewed as a combination of two very different halves.

The right half (as the structure is usually drawn) resembles the nucleus of many of the substituted benzene-ring containing components found throughout the lichen world. Isolation of these products can give the raw materials that can be converted to the compound olivetol, a simple amyl-substituted resorcinol compound.

The left half is a terpene which contains ten carbon atoms, and which is substantially identical to the essential oil, pulegone. This component makes up some 80 to 90% of the Oil of Pennyroyal.

The fusion of these two materials has been shown (Claussen et al., Tetrahedron Vol. 24 p. 2879 (1968)), to produce several products, one of which is delta-3-THC. This is a close structural isomer of delta-9-THC, the principal active component of marijuana, and is known to be active in man.

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Again, I'm about finished with my cannabinoid research.

...and though I use cannabis flowers and Hashish daily, and I use hash and marijuana flowers as an entheogen and meditation aide, and though I love chemistry and psychoactives, I think I have learned enough in this area.

I see marijuana in a way that most people see...let's say coffee, I use it every day, it has slight psychogogical effect, and I enjoy it....but you don't see coffee drinkers obsessing over their coffee the way marijuana users (specially recreational marijuana users) do. I think marijuana needs to be normalized and incorporated into daily life, and it's these people who obsesssvely "make a big deal" about their marijuana, and who treat it like a street drug who are misusing marijuana...I see marijuana as a daily sacrament, it's something jah has put here to keep man stress-free, relaxed, healthy, happy, and sending vibrations of happiness, comfort, peace, love and unity into their surrounding world.

...watch the movie "half-baked", everything in that movie is a perfect example of what Im talking about, every single way those people act towards and use marijuana, it's these attitudes and behaviors that I dislike...but that's a discussion for another thread...

-eg
 
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