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Old 12-23-2010, 02:49 AM #1
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Secondary metabolites (of cannabis)

Hey all,

The genesis for this thread was a request from a buddy (VF) who asked for recent studies about CBD. It took me longer than I had hoped to collect all of these, but I have enough to start a good thread I think. There are three other threads* in this science sub-forum that also have some relevant studies where Pipeline, Cannaboloist and myself uploaded many studies. Instead of re-uploading the papers again I will link to relevant posts in other threads were appropriate.
* there are two separate threads with the same topic, one is by Pipeline and one by Cananboloist. I think they should be merged into one thread because they both are for the same thing: uploading cannabis specific scholarly papers/research. I think having two of the same threads makes finding studies less easy. The thread by Pipeline was first, so I am humbly ask OldPink (or any other mod) to merge Cannabologist's thread into Pipeline's thread. The third thread is mine, it's a 'request' thread where people can post studies they want to read, but don't have access to. Then myself and others, do our best to get the requested studies and upload them for our fellow Icers.

I will add to this thread as time goes on, but for now I have maybe a dozen or two papers to upload. That should be enough for now, I hope

This thread isn't only about CBD and other cannabinoids, it's also about other secondary metabolites like flavonoids and terpenoids (which are not tepenes, even though they come from tepenes, thus calling terpenoids, terpenes, should be avoided).

OK, here goes. I was going to post the title, authors and journal, along with the abstracts, but posting abstracts takes a while because they have to be formatted correctly. I might post the abstracts at a later date, but now I don't have enough time.


1. General studies on various secondary metabolites in cannabis including THC, CBD, CBC, terpenoids, etc.:


"Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts?"
John M. McPartland and Ethan B. Russo
Journal of Cannabis Therapeutics (2001), Vol.1, No.3/4, pp. 103-132

"Comparison of the subjective effects of ∆9-tetrahydrocannabinol and marijuana in humans"
S. R. Wachtel, M. A. ElSohly, S. A. Ross and J. Ambre H. de Wit
Psychopharmacology (2002) 161:331–339


"Cannabis is more than simply ∆9-tetrahydrocannabinol"
Ethan B. Russo and John M. McPartland
Psychopharmacology (2003) 165:431–432

"Cannabis versus THC: response to Russo and McPartland"
Mahmoud A. ElSohly, Stephen R. Wachtel and Harriet Wit
Psychopharmacology (2003) 165:433–434

"Secondary metabolism in cannabis"
Isvett Josefina Flores-Sanchez and Robert Verpoorte
Phytochem Rev (2008) 7:615–639

"Recent advances in Cannabis sativa research: biosynthetic studies and its potential in biotechnology"
Sirikantaramas S, Taura F, Morimoto S, Shoyama Y.
Curr Pharm Biotechnol. 2007 Aug;8(4):237-43

"A historical overview of chemical research on cannabinoids"
Raphael Mechoulam and Lumır Hanus
Chemistry and Physics of Lipids 108 (2000) 1–13
  • uploaded to this post

"Cannabis Plant Chemistry"
Montana Medical Grower’s Association, in conjunction with Montana Botanical Analysis
  • uploaded to this post


"Chemistry and Analysis of Phytocannabinoids and Other Cannabis Constituents"
Rudolf Brenneisen
From: Forensic Science and Medicine: Marijuana and the Cannabinoids
  • uploaded to this post

"Chemical constituents of marijuana: The complex mixture of natural cannabinoids"
Mahmoud A. ElSohly and Desmond Slade
Life Sciences 78 (2005) 539–548
  • uploaded to this post

[not so...] "Recent Developments in Cannabis Chemistry"
ALEXANDER T. SHULGIN, Ph.D.
Journal of Psychedelic Drugs, vol. II, no. 1 (1971)
  • uploaded to this post

"Human Studies of Cannabinoids and Medicinal Cannabis"
P. Robs on
HEP (2005) 168:719–756
  • uploaded to this post

2. Endocannabinoid system and cytokine network:


"Cannabinoids, Immune System and Cytokine Network"
Massi, P.1; Vaccani, A.1; Parolaro, D.1
Current Pharmaceutical Design, Volume 12, Number 24, August 2006 , pp. 3135-3146(12)

"The Cannabinoid System and Cytokine Network"
Thomas W. Klein, Brian Lane, Catherine A. Newton, Herman Friedman
Proceedings of the Society for Experimental Biology and Medicine
Volume 225, Issue 1, pages 1–8, October 2000


"THE ENDOCANNABINOID SYSTEM AND ITS THERAPEUTIC EXPLOITATION"
Vincenzo Di Marzo,Maurizio Bifulco and Luciano De Petrocellis
NATURE REVIEWS, VOLUME 3, SEPTEMBER 2004


"The Endocannabinoid System and the Therapeutic Potential of Cannabinoids"
Billy R. Martin
From: Forensic Science and Medicine: Marijuana and the Cannabinoids


"THE NEURONAL, ENDOCRINE, METABOLIC EFFECTS OF ENDOCANNABINOID SYSTEM AND THE POTENTIAL CLINICAL IMPLICATIONS OF THE CANNABINOID TYPE 1 (CB1) BLOCKER"
JOURNAL OF ENDOCRINOLOGICAL INVESTIGATION, Vol. 29, Suppl. to No. 3 (2006)
  • Includes the following studies:
  1. "The chemistry of endocannabinoids". N.M. Kogan, and R. Mechoulam.
  2. "Endocannabinoid synthesis and degradation, and their regulation in the framework of energy balance". I. Matias, and V. Di Marzo
  3. "Neuromodulatory functions of the endocannabinoid system". G. Marsicano, and B. Lutz
  4. "Endocannabinoids and the gastrointestinal tract". F. Massa, and K. Monory
  5. "Endocannabinoids and energy metabolism". U. Pagotto, and R. Pasquali
  6. "Endocannabinoids as novel mediators of liver diseases". A. Mallat, and S. Lotersztajn


3. Cannabinoids: THC, CBD, etc (natural and synthetic):


"Pharmacological Actions of Cannabinoids"
R. G. Pertwee
Cannabinoids, Handbook of Experimental Pharmacology, 2005, Volume 168, 1-51


"The acute effects of synthetic intravenous D9-tetrahydrocannabinol on psychosis, mood and cognitive functioning"
P. D. Morrison, V. Zois, D. A. McKeown, T. D. Lee, D. W. Holt, J. F. Powell, S. Kapur and R. M. Murray
Psychological Medicine (2009), 39, 1607–1616
  • I have always thought about I.V. THC extract would be very useful for some very sick people, Sam Skunkman has written I.V. of THC has no affect, after reading this paper I am not sure Sam is correct...
  • uploaded to this post


"A tale of two cannabinoids: The therapeutic rationale for combining tetrahydrocannabinol and cannabidiol"
Ethan Russo and Geoffrey W. Guy
Medical Hypotheses (2006) 66, 234–246
  • This paper is one of the bases for "Sativex", from GW Pharmaceuticals with the assistance of HotraPharm BV (for triploid cannabis plants from seed - which HotraPharm BV terms "clones", growing info, etc); Sativex is marketed by Beyer Drugs for GW Pharmaceuticals. Sativex is 50/50 THC/CBD IIRC.
  • upload to this post

"Does cannabidiol protect against the negative effects of THC?"
Cécile Henquet and Rebecca Kuepper
The British Journal of Psychiatry, (2010) 197: 259-260
  • uploaded to this post

"Cannabidiol potentiates pharmacological effects of D9-tetrahydrocannabinol via CB1 receptor-dependent mechanism"
Kazuhide Hayakawaa, Kenichi Mishimaa, Mai Hazekawaa, Kazunori Sanoa, Keiichi Iriea, Kensuke Oritoc, Takashi Egawaa, Yoshihisa Kitamuraa, Naoki Uchidad, Ryoji Nishimurad, Nobuaki Egashiraa, Katsunori Iwasaki and Michihiro Fujiwara
BRAIN RESEARCH 1188 (2008) 157 – 164
  • uploaded to this post




OK, I ran out upload space in this post, I will continue with uploading studies in my next post. Please do not respond to this thread until I am done uploading studies, thanks
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Old 12-23-2010, 04:09 AM #2
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3. (cont.) THC and CBD


"Cannabinoid Receptor 1 Binding Activity and Quantitative Analysis of Cannabis sativa L. Smoke and Vapor"
Justin FISCHEDICK, Frank VAN DER KOOY and Robert VERPOORTE
Chem. Pharm. Bull. 58(2) 201—207 (2010)
  • uploaded to this post


"Pharmacological and therapeutic targets for ∆9-tetrahydrocannabinol and cannabidiol"
Roger G. Pertwee
Euphytica 140: 73–82, 2004.
  • uploaded to this post


"Action of Cannabidiol on the Anxiety and Other Effects Produced by D9-THC in Normal Subjects"
A.W. Zuardi, I. Shirakawa, E. Finkelfarb and I.G. Karniol
Psychopharmacology (1982) 76:245-250
  • uploaded to this post



"Cannabidiol: an overview of some chemical and pharmacological aspects. Part I: chemical aspects"
Raphael Mechoulam, Lumır Hanus
Chemistry and Physics of Lipids 121 (2002) 35-43
  • uploaded to this post


"Cannabidiol: an overview of some pharmacological aspects"
R Mechoulam, LA Parker and R Gallily
J Clin Pharmacol (2002) 42: 11S
  • uploaded to this post


"Cannabidiol: from an inactive cannabinoid to a drug with wide spectrum of action"
Antonio Waldo Zuardi
Rev Bras Psiquiatr. 2008;30(3):271-80
  • uploaded to this post


"Cannabidiol as a potential medicine"
Roger G. Pertwee
From: Cannabinoids as Therapeutics. (2005) Edited by R. Mechoulam
  • uploaded to this post


"Impact of cannabidiol on the acute memory and psychotomimetic effects of smoked cannabis: naturalistic study"
Celia J. A. Morgan, Gráinne Schafer, Tom P. Freeman and H. Valerie Curran
The British Journal of Psychiatry (2010) 197: 285-290
  • uploaded to this post


"Cannabidiol"
Peter G. Jones, Larry Falvello, Olga Kenenard and George M. Sheldrick
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, (1977) Volume 33, Part 10, pp. 3211-3214


4. Tepenoids:



"A chemotaxonomic analysis of terpenoid variation in Cannabis"
Karl W. Hillig
Biochemical Systematics and Ecology 32 (2004) 875–891


"The Volatile Oil Composition of Fresh and Air-Dried Buds of Cannabis sativa"
Samir A. Rossi and Mahmoud A. ElSohly
J. Nut. Prod. 1996, 59, 49-51
  • uploaded to this post



"Essential oil of Cannabis sativa L. strains"
Vito Mediavilla and Simon Steinemann
Journal of the International Hemp Association, (1997) 4(2): 80-82[list][*]online here:https://www.internationalhempassociat.../jiha4208.html[/LIST



"Plant terpenoids: applications and future potentials"
Sam Zwenger and Chhandak Basu
Biotechnology and Molecular Biology Reviews, (2008) Vol. 3 (1), pp. 001-007


"Chemistry Of Terpenoids And Carotenoids"
G. Singh
Discovery Publishing House (2008) ISBN 8183562795, 9788183562799
  • This book was written for B.Sc, B.Sc. (Hons.) and M.Sc., students. And what I find funny about that book is on the front cover is a picture of a nice cannabis bud, but when searching the book for the terms "cannabis", "marijuana" and "hemp" I found nothing...odd



OK, I'm done upload papers for now. If anyone has papers they think are relevant to this thread please feel free to upload them! I will add to this thread in the near future...

Attached Files
File Type: pdf Pharmacological and therapeutic.PDF (107.1 KB, 11 views)
File Type: pdf Action of Cannabidiol.PDF (695.6 KB, 21 views)
File Type: pdf Review cannabidiol part 1.PDF (239.0 KB, 15 views)
File Type: pdf cannbidiol an overview.PDF (233.6 KB, 16 views)
File Type: pdf Cannabidiol from an inactive cannabinoid to a drug.PDF (666.3 KB, 13 views)
File Type: pdf Cannabidiol as a potential medicine.pdf (133.3 KB, 13 views)
File Type: pdf Impact of cannabidiol on the acute.PDF (341.8 KB, 13 views)
File Type: pdf Cannabinoid Receptor 1 Binding.PDF (203.0 KB, 15 views)
File Type: pdf The Volatile Oil Composition.PDF (372.9 KB, 16 views)
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Old 09-25-2012, 06:37 PM #3
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What the f***ing f***.... Amazing posts.
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Old 09-25-2012, 09:39 PM #4
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I concur great links!

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Old 10-06-2012, 04:34 AM #5
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Where is the discussion? This is a great archive!!!

Damn shame shit like this gets overlooked.....
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Old 10-11-2012, 02:22 AM #6
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I agree. I've been thinking about starting a thread that is similar to this but wasn't sure if this section or the medical section would be more appropriate. Well then, lets get the discussion rolling then shall we.........
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Old 10-16-2012, 05:00 PM #7
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Holy cow, what an amazingly useful trove of information. Thanks for posting.
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Old 10-16-2012, 05:07 PM #8
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Nice job Spurr wow lots of material to read lol tanks headband 707
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Old 10-30-2012, 07:33 AM #9
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Polyketide synthases in Cannabis sativa L

Isvett J. Flores Sanchez • Robert Verpoorte

Pharmacognosy Department, Institute of Biology, Gorlaeus Laboratories, Leiden
University
Leiden, The Netherlands
Published in Phytochem Rev (2008) 7:615-639

Cannabis sativa L. is an annual dioecious plant from Central Asia.
Cannabinoids, flavonoids, stilbenoids, terpenoids, alkaloids and lignans are some of the secondary metabolites present in C. sativa. Earlier reviews focused on isolation and identification of more than 480 chemical compounds; this review deals with the biosynthesis of the secondary metabolites present in this plant. Cannabinoid biosynthesis and some closely related pathways that involve the same precursors are discussed.

Full Text
https://openaccess.leidenuniv.nl/bits...pdf?sequence=2

I.4 Outline of the thesis
The studies described in this thesis are focused on biochemical and molecular aspects of PKSs involved in the biosynthesis of precursors from cannabinoid, flavonoid or stilbenoid pathways. A review about general aspects of plant PKS is given in Chapter 2. Enzymatic activities of PKSs in plant cannabis tissues and a correlation with the content of cannabinoids and flavonoids is described in Chapter 3. Isolation of PKS mRNAs and an expression in silicio are presented in Chapter 4. Finally, as cell cultures can be used as model systems to study secondary metabolite biosynthesis, cannabis cell suspension cultures were treated with biotic and abiotic elicitors to evaluate their effect on the cannabinoid biosynthesis (Chapter 5).

Chapter 1
https://openaccess.leidenuniv.nl/bits...D8E?sequence=6

Chapter 2
https://openaccess.leidenuniv.nl/bits...pdf?sequence=7

Chapter 3
https://openaccess.leidenuniv.nl/bits...pdf?sequence=8

Chapter 4
https://openaccess.leidenuniv.nl/bits...pdf?sequence=9

Chapter 5
https://openaccess.leidenuniv.nl/bits...df?sequence=10

Concluding remarks and perspectives
https://openaccess.leidenuniv.nl/bits...df?sequence=11

Summary
https://openaccess.leidenuniv.nl/bits...df?sequence=12

References
https://openaccess.leidenuniv.nl/bits...df?sequence=14

Propositions
https://openaccess.leidenuniv.nl/bits...pdf?sequence=1

A great overview of plant metabolism from the man who taught me Pharmacognosy, Dr. Eric Yarnell, ND, RH (AHG). With this overview the Figure 15. A general scheme of the primary and secondary metabolism in C. sativa. found in Chapter 1 pg. 28 (the last page in Chapter 1) will hopefully be more useful.





Yarnell, ND, RH (AHG), Eric L. Phytochemistry And Pharmacy For Practitioners Of Botanical Medicine. Washington: Healing Mountain Publishing, Inc., 2004. Print.


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Old 10-30-2012, 06:23 PM #10
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great post thanks!
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