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Changing Medicine Together
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Molecular Structure of Cannabis
And There Synthetic Molecular Copy
Note: There are 2 types of natural cannabiniods; Ones produced in the body, the other in plants.
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Informative Video's on Page
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Cannabinoid Receptors Cannabinoids
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Pharmaceutical Synthetic Cannabiniods
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Note: THC, CBD, CBC Originate from CBGA, geranyl pyrophosphate combined with olivetolic acid create CBGA. then THCA, CBDA,CBCA from CBGA decarboxylation transforms into THC, CBD & CBC.
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Cannabinoid Profiles -
THC, THC-A, THC-V, CBD, CBG, CBN, CBC & Terpenes |
Note: THCV, CBDV, are a finished chemicals like THC, & CBD. THCV don't originate from CBGA, instead geranyl pyrophosphate joins with divarinolic acid, which has two fewer carbon atoms, resulting in CBGVA, from there it's broken down to THCVA etc, to decarboxylation into THCV, CBDV & CBCV
Endo-cannabiniods; Body produced cannabiniods
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Anandamide
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2-AG
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Chemical Name: Anandamide, N-arachidonoylethanolamine AEA,
IUPAC name (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl) icosa-5,8,11,14-tetraenamide Molecular Formula: C22H37NO2 Molar Mass: 347.53 g/mol |
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Chemical Name: 2-Arachidonoylglycerol (2-AG)
IUPAC name 1,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z) - 5,8,11,14-eicosatetraenoate Molecular Formula: C23H38O4 Molar Mass: 378.3/g/mol |
Phyto-cannabiniods; Plant Produced cannabiniods
Tetrahdyrocannabinol (THC)
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Chemical Name: (6aR,10aR)-delta-9-tetrahydrocannabinol, (−)-trans-Δ⁹- tetrahydrocannabinol
Molecular Formula: C21H30O2 Molecular Weight: 314.469 g/mol Boiling point: 155-157°C @ 0.05mmHg, 157-160°C @ 0.05mmHg Solubility in water: 0.0028, (23 °C) mg/mL (20 °C) Bioavailability, Inhaled: 10–35%, Oral: 6 - 20% Protein binding: 97–99% Biological half-life: 1.6–59 h, 25–36 h (orally administered dronabinol |
For a review of the mechanisms behind endocannabinoid synaptic transmission, see Endocannabinoid system.
The actions of THC result from its partial agonist activity at the cannabinoid receptor CB1 (Ki=10nM), located mainly in the central nervous system, and the CB2 receptor (Ki=24nM), mainly expressed in cells of the immune system. The psychoactive effects of THC are primarily mediated by the activation of cannabinoid receptors, which result in a decrease in the concentration of the second messenger molecule cAMP through inhibition of adenylate cyclase.
The actions of THC result from its partial agonist activity at the cannabinoid receptor CB1 (Ki=10nM), located mainly in the central nervous system, and the CB2 receptor (Ki=24nM), mainly expressed in cells of the immune system. The psychoactive effects of THC are primarily mediated by the activation of cannabinoid receptors, which result in a decrease in the concentration of the second messenger molecule cAMP through inhibition of adenylate cyclase.
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Cannabinoids
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Biosynthesis Of THCA
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Tetrahydrocannabinolic Acid (THCA)
Chemical Name: Tetrahydrocannabinolic Acid (THCA)
Molecular Formula: C22H30O4
Molecular Weight: 358.4733 g/mol
Boiling Point:
General Information
Molecular Formula: C22H30O4
Molecular Weight: 358.4733 g/mol
Boiling Point:
General Information
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Tetrahydrocannabinolic acid (THCA, 2-COOH-THC; conjugate base tetrahydrocannabinolate) is a precursor of tetrahydrocannabinol (THC), the active component of cannabis. THCA is found in variable quantities in fresh, undried cannabis, but is progressively decarboxylated to THC with drying, and especially under intense heating such as when cannabis is smoked or cooked into cannabis edibles. THCA is often the majority constituent in cannabis resin concentrates, such as [hashish] and hash oil, when prepared from high-THC cannabis plant material, frequently comprising between 50% and 90% by weight. It has two isomers, THCA-A, in which the carboxyl group is in the 1 position, between the hydroxyl group and the carbon chain, and THCA-B,
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(THCA) Tetrahydrocannabinolic Acid
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in which the carboyxl group is in the 3 position, following the carbon chain. In the past THCA was thought to be formed in plants by cyclization of cannabidiolic acid but studies but in the late 1990s it became apparent that its precursor is cannabigerolic acid, which goes through oxidocyclization through the actions of the enzyme THCA-synthase. It is unstable, and slowly decarboxylates into THC during storage, and the THC itself slowly degrades to cannabinol. When heated or burned, as when cannabis is smoked or included in baked goods, the decarboxylation is rapid but not complete; THCA is detectable in people who smoke or otherwise consume cannabis
Tetrahydrocannabivarin (THCV)
Chemical Name: Tetrahydrocannabivarin (THCV, THV)
Molecular Formula: C19H26O2
Molecular Weight: 286.41 g/mol
Boiling Point: 220 degrees C (428 degrees F )
Molecular Formula: C19H26O2
Molecular Weight: 286.41 g/mol
Boiling Point: 220 degrees C (428 degrees F )
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Tetrahydrocannabivarin (THCV, THV) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of a pentyl (5-carbon) group on the molecule, which makes it produce very different effects from THC.[1] This terpeno-phenolic compound is found naturally in Cannabis, sometimes in significant amounts. The psychoactive effects of THCV in Cannabis preparations are not well characterized. At lower doses, THCV may act as a CB1 antagonist. At higher doses, however, it can switch, behaving as a CB1 agonist, much like THC.
Chemistry Similarly to THC, THCV has 7 double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism). Its melting point is < 220 degrees Celsius, < 428 degrees Fahrenheit. |
(THCV) Tetrahydrcannabivarin
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Description
Plants with elevated levels of propyl cannabinoids (including THCV) have been found in populations of Cannabis sativa L. ssp. indica (= Cannabis indica Lam.) from China, India, Nepal, Thailand, Afghanistan, and Pakistan, as well as southern and western Africa. THCV levels up to 53.7% of total cannabinoids have been reported.
THCV is a cannabinoid receptor type 1 antagonist and cannabinoid receptor type 2 partial agonist. Δ8-THCV has also been shown to be a CB1 antagonist. Both papers describing the antagonistic properties of THCV were demonstrated in murine models.
Biosynthesis
Unlike THC, cannabidiol (CBD), and cannabichromene (CBC), THCV doesn’t begin as cannabigerolic acid (CBGA). Instead of combining with olivetolic acid to create CBGA, geranyl pyrophosphate joins with divarinolic acid, which has two fewer carbon atoms. The result is cannabigerovarin acid (CBGVA). Once CBGVA is created, the process continues exactly the same as it would for THC. CBGVA is broken down to tetrahydrocannabivarin carboxylic acid (THCVA) by the enzyme THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV.
Plants with elevated levels of propyl cannabinoids (including THCV) have been found in populations of Cannabis sativa L. ssp. indica (= Cannabis indica Lam.) from China, India, Nepal, Thailand, Afghanistan, and Pakistan, as well as southern and western Africa. THCV levels up to 53.7% of total cannabinoids have been reported.
THCV is a cannabinoid receptor type 1 antagonist and cannabinoid receptor type 2 partial agonist. Δ8-THCV has also been shown to be a CB1 antagonist. Both papers describing the antagonistic properties of THCV were demonstrated in murine models.
Biosynthesis
Unlike THC, cannabidiol (CBD), and cannabichromene (CBC), THCV doesn’t begin as cannabigerolic acid (CBGA). Instead of combining with olivetolic acid to create CBGA, geranyl pyrophosphate joins with divarinolic acid, which has two fewer carbon atoms. The result is cannabigerovarin acid (CBGVA). Once CBGVA is created, the process continues exactly the same as it would for THC. CBGVA is broken down to tetrahydrocannabivarin carboxylic acid (THCVA) by the enzyme THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV.
Cannabidiol (CBD)
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Chemical Name: Cannabidiol; (-)-trans-Cannabidiol; 13956-29-1; (-)-trans-2-p-Mentha-1,8-dien-3-yl-5-pentylresorcinol
Molecular Formula: C21H30O2 Molecular Weight: 314.469g/mol Melting Point: 66 °C (151 °F) Bioavailability, Oral: 13 - 19% Inhaled: 11 - 45% Biological Half Life: 9 hrs Cannabidiol is a phytocannabinoid derived from Cannabis species, which is devoid of psychoactive activity, with analgesic, anti-inflammatory, antineoplastic and chemopreventive activities. Upon administration, cannabidiol (CBD) exerts its anti-proliferative, anti-angiogenic and pro-apoptotic activity through various mechanisms, which |
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likely do not involve signaling by cannabinoid receptor 1 (CB1), CB2, or vanilloid receptor 1. CBD stimulates endoplasmic reticulum (ER) stress and inhibits AKT/mTOR signaling, thereby activating autophagy and promoting apoptosis. In addition, CBD enhances the generation of reactive oxygen species (ROS), which further enhances
apoptosis. This agent also upregulates the expression of intercellular adhesion molecule 1 (ICAM-1) and tissue inhibitor of matrix metalloproteinases-1 (TIMP1) and decreases the expression of inhibitor of DNA binding 1 (ID-1). This inhibits cancer cell invasiveness and metastasis. CBD may also activate the transient receptor potential vanilloid type 2 (TRPV2), which may increase the uptake of various cytotoxic agents in cancer cells. The analgesic effect of CBD is mediated through the binding of this agent to and activation of CB1. |
(CBD) Cannabidiol
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Cannabidiolic Acid (CBDA)
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Chemical Name: Cannabidiolic Acid (CBDA)
Molecular Formula: C22H30O4 Molecular Weight: 358.47 g/mol General description Cannabidiolic acid (CBDA) is a non-psychoactive cannabinoid found in Cannabis that reportedly has therapeutic efficacy in the treatment of cancer. This Certified Spiking Solution® is suitable for cannabidiolic acid testing methods by GC/MS, LC/MS or HPLC for applications in testing of Cannabis potency or impurity profiling, pharmaceutical research, and forensic analysis. Cerilliant solution Certified Reference Materials (CRMs) of cannabinoids are supplied in a convenient, quantitative, US DEA-exempt solution format and with TK#s for Canadian customers. |
(CBDA) Cannabidiolic Acid
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Cannabidivarin (CBDV)
Chemical Name: Cannabidivarin (CBDV)
Molecular Formula: C19H26O2
Molecular Weight: 286.41 g/mol
Boiling Point:
Molecular Formula: C19H26O2
Molecular Weight: 286.41 g/mol
Boiling Point:
Cannabidivarin (CBDV) is a non-psychoactive cannabinoid found in Cannabis. It is a homolog of cannabidiol (CBD), with the side-chain shortened by two methylene bridges (CH2 units). Plants with relatively high levels of CBDV have been reported in feral populations of C. indica ( = C. sativa ssp. indica var. kafiristanica) from northwest India, and in hashish from Nepal. CBDV has anticonvulsant effects.
Similarly to CBD, it has 7 double bond isomers and 30 stereoisomers (see: Cannabidiol#Double bond isomers and their stereoisomers). It is not scheduled by Convention on Psychotropic Substances. It is being actively developed by GW Pharmaceuticals (as GWP42006) because of a demonstrated neurochemical pathway for previously-observed anti-epileptic and anti-convulsive action. GW has begun a phase 2 trial for adult epilepsy and is to begin trials of this CBDV product in children in 2016 in Australia.
Similarly to CBD, it has 7 double bond isomers and 30 stereoisomers (see: Cannabidiol#Double bond isomers and their stereoisomers). It is not scheduled by Convention on Psychotropic Substances. It is being actively developed by GW Pharmaceuticals (as GWP42006) because of a demonstrated neurochemical pathway for previously-observed anti-epileptic and anti-convulsive action. GW has begun a phase 2 trial for adult epilepsy and is to begin trials of this CBDV product in children in 2016 in Australia.
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Cannabigerol (CBG)
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Cannabigerol (CBG) is a non-intoxicating cannabinoid found in the Cannabis genus of plants, as well as certain other plants including Helichrysum umbraculigerum.[1] CBG is the non-acidic form of cannabigerolic acid (CBGA), the parent molecule (“mother cannabinoid”) from which many other cannabinoids are made. By the time most strains of cannabis reach maturity, most of the CBG has been converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD), usually leaving somewhere
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below 1% CBG in the plant. CBG has been found to act as a high affinity α2-adrenergic receptor agonist, moderate affinity 5-HT1A receptor antagonist, and low affinity CB1 receptor antagonist. It also binds to the CB2 receptor as an antagonist. CBG does not trigger THC-like activity in mice, rats, gerbils and non-human primates, consistent with it being non-intoxicating. Moreover, CBG was without effect up to 80 mg/kg in the mouse tetrad test of cannabimimetic activity (locomotor suppression, catalepsy, hypothermia and analgesia).
Cannabigerolic Acid (CBGA)
Chemical Name: CBGA
Molecular Formula: C22H32O4
Molecular Weight: 360.49 g/mol
General description
A non-psychoactive cannabinoid, cannabigerolic acid (CBGA), is the precursor to THCA, CBDA, and CBCA cannabinoids in Cannabis. Cannabigerolic acid reportedly has efficacy in treatment of cancer and schizophrenia. This Certified Spiking Solution® is suitable for CBGA testing methods by HPLC, LC/MS, or GC/MS for applications in testing of Cannabis potency or impurity profiling, pharmaceutical research, and forensic analysis.
Molecular Formula: C22H32O4
Molecular Weight: 360.49 g/mol
General description
A non-psychoactive cannabinoid, cannabigerolic acid (CBGA), is the precursor to THCA, CBDA, and CBCA cannabinoids in Cannabis. Cannabigerolic acid reportedly has efficacy in treatment of cancer and schizophrenia. This Certified Spiking Solution® is suitable for CBGA testing methods by HPLC, LC/MS, or GC/MS for applications in testing of Cannabis potency or impurity profiling, pharmaceutical research, and forensic analysis.
Cannabichromene (CBC)
Cannabichromene (CBC) is ultimately formed when its precursor acid form, Cannabichrome Carboxylic Acid (CBCa), is converted to its neutral form - CBC. CBCa is one of the three major cannabinoid branches formed by Cannabigerolic Acid (CBGa). The cannabis plant possesses natural enzymes, referred to as "synthases", that break the CBGa down and convert it to one of the major cannabinoids. As shown in this graphic, we see how CBC is formed via decarboxylation of CBCa. Out of the big three cannabinoids (THC, CBD & CBC), Cannabichromene (CBC) rarely gets any attention beyond a mention. Unlike Tetrahydrocannabinol (THC), CBC does not share its psychoactive effects. SIDEBAR: You might see claims asserting that CBC is the second most concentrated cannabinoid in the plant after THC. My research indicates that assertion is based on only two studies and is not accurate. As described on the Cannabis Library page, cannabinoids interact with the CB1-R and CB2-R receptors, but they also interact with other receptors, too. CBC is known to interact with the TRPV1 receptor and other receptors as well. The research on CBC continues to indicate that it might modulate the effect of THC and other cannabinoids in important tways.
In addition to the possible medical benefits listed below, there's also now a growing interest in CBC's potential to treat gastrointestinal and inflammatory disorders and many other Ailments.
- Anti-bacterial effects: Study 1; Study 2
- Analgesic/pain relieving benefits: Study 1;Study 2
- May help inhibit depression: Study 1
- CBC may increase the viability of developing brain cells, a process known as neurogenesis. Study 1
- Might be neuroprotective, but may have opposite effect too: Study 1
- Stimulate bone growth,
In addition to the possible medical benefits listed below, there's also now a growing interest in CBC's potential to treat gastrointestinal and inflammatory disorders and many other Ailments.
- Anti-bacterial effects: Study 1; Study 2
- Analgesic/pain relieving benefits: Study 1;Study 2
- May help inhibit depression: Study 1
- CBC may increase the viability of developing brain cells, a process known as neurogenesis. Study 1
- Might be neuroprotective, but may have opposite effect too: Study 1
- Stimulate bone growth,
Cannabicyclol (CBL)
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Cannabicyclol, also called CBL, is one of the least known and studied cannabinoids in the cannabis plant. Although it is commonly found in many varieties, in particular those with a higher content of CBC (Cannabichromene), the amount of CBL produced in trichomes is always very low, One of the main characteristics of CBL is the absence of psychoactivity in its effect, which is why it is not listed in the Convention of Psychotropic Substances. In fact, CBL shares its formula with many of the other phytocannabinoids produced by cannabis, even with psychoactive compounds, although it differs slightly – as in the other cases – in its structure, in the ordering of the atoms that make up the molecule, meaning that its effects vary enormously. For example, THC or tetrahydrocannabinol (the main psychoactive cannabinoid of cannabis) and CBL differ mainly in the absence of double bond in the second molecule.
CBL synthesis
As with other cannabinoids found in marijuana, In this case, Cannabicyclol CBL comes from the degradation of CBC, mainly by the action of light; When the CBC is subjected to oxygen or UV light, CBL is obtained. The plant produces very small amounts of CBL-A, the acidic form of CBL. Although, it is very difficult to decarboxylate CBL, being the most resistant cannabinoid to this process, so getting the active form (CBL) from the acid (CBL-A) is complicated.
like CBG (Cannabigerol) is the precursor of the different cannabinoids found in marijuana.
Properties of CBL
Given that, as we have seen, cannabis plants produce only a small quantity of this cannabinoid, research on this compound is unfortunately also very scarce. Many more studies are needed to determine the possible medicinal properties of CBL, and the rest of the cannabinoids and terpenes in the known entourage effect.
However, recent studies by Steep Hill Labs have shown promising conclusions, especially regarding the anti-inflammatory potential and anti-tumor effect of CBL.
the conclusions presented by Steep Hill Labs are promising regarding certain therapeutic properties of CBL, many more studies are necessary
CBL synthesis
As with other cannabinoids found in marijuana, In this case, Cannabicyclol CBL comes from the degradation of CBC, mainly by the action of light; When the CBC is subjected to oxygen or UV light, CBL is obtained. The plant produces very small amounts of CBL-A, the acidic form of CBL. Although, it is very difficult to decarboxylate CBL, being the most resistant cannabinoid to this process, so getting the active form (CBL) from the acid (CBL-A) is complicated.
like CBG (Cannabigerol) is the precursor of the different cannabinoids found in marijuana.
Properties of CBL
Given that, as we have seen, cannabis plants produce only a small quantity of this cannabinoid, research on this compound is unfortunately also very scarce. Many more studies are needed to determine the possible medicinal properties of CBL, and the rest of the cannabinoids and terpenes in the known entourage effect.
However, recent studies by Steep Hill Labs have shown promising conclusions, especially regarding the anti-inflammatory potential and anti-tumor effect of CBL.
the conclusions presented by Steep Hill Labs are promising regarding certain therapeutic properties of CBL, many more studies are necessary
Cannabinol (CBN)
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CBN, or cannabinol, is a mildly psychoactive cannabinoid found in smaller concentrations in cannabis than its more famous cousins like THC and CBD. Unlike those cannabinoids, however, cannabinol does not directly derive from the precursor molecule, CBG. Rather,
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CBN is derived from the oxidation of THCA. As dried cannabis ages, THCA naturally converts into CBNA, the direct precursor of CBN. As such, the overall content of CBNA may broadly be used to ascertain the age of dried cannabis; the more it contains, the older it is.
CBN Medical Research
As is the case for other cannabinoids, medical research into the potential medical properties of cannabinol is currently ongoing. Below we present a small sample of peer-reviewed investigation.
ALS: Cannabinol delays symptom onset in SOD1 (G93A) transgenic mice without affecting survival
Analgesic: Δ9-Tetrahydrocannabinol and Cannabinol Activate Capsaicin-Sensitive Sensory Nerves via a CB1 and CB2 Cannabinoid Receptor-Independent Mechanism
Antibacterial: Antibacterial cannabinoids from Cannabis sativa: a structure-activity study
Appetite: Cannabinol and cannabidiol exert opposing effects on rat feeding patterns
Inflammation: Cannabinoids and the immune system:Potential for the treatment of inflammatory disease.
CBN Medical Research
As is the case for other cannabinoids, medical research into the potential medical properties of cannabinol is currently ongoing. Below we present a small sample of peer-reviewed investigation.
ALS: Cannabinol delays symptom onset in SOD1 (G93A) transgenic mice without affecting survival
Analgesic: Δ9-Tetrahydrocannabinol and Cannabinol Activate Capsaicin-Sensitive Sensory Nerves via a CB1 and CB2 Cannabinoid Receptor-Independent Mechanism
Antibacterial: Antibacterial cannabinoids from Cannabis sativa: a structure-activity study
Appetite: Cannabinol and cannabidiol exert opposing effects on rat feeding patterns
Inflammation: Cannabinoids and the immune system:Potential for the treatment of inflammatory disease.
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Ted Talk Cannabis Saving More Lives Big & Little
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Clinical Application of Cannabinoids and Terpenes | M. Gordon
Very informative, With application knowledge
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