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13956-29-1

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Basic Information
CAS No.: 13956-29-1
Name: CANNABIDIOL
Article Data: 50
Molecular Structure:
Molecular Structure of 13956-29-1 (CANNABIDIOL)
Formula: C21H30 O2
Molecular Weight: 314.468
Synonyms: 1,3-Benzenediol,2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, (1R-trans)-;Cannabidiol (7CI); Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, trans-(-)-(8CI); (-)-CBD; (-)-Cannabidiol; (-)-trans-Cannabidiol; CBD; D1(2)-trans-Cannabidiol
EINECS: 200-659-6
Density: 1.025 g/cm3
Melting Point: 62-63°C
Boiling Point: 463.9 °C at 760 mmHg
Flash Point: 206.3 °C
Hazard Symbols: FlammableFToxicT
Risk Codes: 11-23/24/25-39/23/24/25
Safety: Poison by intravenous route. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Transport Information: UN 1230 3
PSA: 40.46000
LogP: 5.84650
Synthetic route

(1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl bis(2,2-dimethylpropanoate)

Conditions
ConditionsYield
With methylmagnesium bromide In diethyl ether; toluene at 110℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;99%
With potassium hydroxide In methanol; dichloromethane at 20℃; Inert atmosphere;91%
Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0℃; for 2h; Solvent;97%
With methyl magnesium iodide In diethyl ether at 0 - 160℃; for 1.5h; Inert atmosphere;62%
With sodium thioethylate In N,N-dimethyl-formamide at 150℃; for 5h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;1.02 g

C30H47NO4

Conditions
ConditionsYield
With sodium hydroxide In methanol at 90℃; for 4h; Inert atmosphere;94%

C25H36O4

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; lithium chloride In dimethyl sulfoxide at 80 - 100℃; Reagent/catalyst; Solvent; Temperature;93%

C26H39NO4

Conditions
ConditionsYield
With sodium hydroxide In methanol at 95℃; for 8h; Inert atmosphere;92%

C28H43NO4

Conditions
ConditionsYield
With sodium hydroxide In methanol at 95℃; for 8h; Inert atmosphere;91%

C30H47NO4

Conditions
ConditionsYield
With sodium hydroxide In methanol at 95℃; for 8h; Inert atmosphere;88%

(1′R,2′R)-2,6-bis((tert-butoxycarbonyl)oxy)-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl trifluoromethanesulfonate

693-25-4

n-pentylmagnesium bromide

Conditions
ConditionsYield
Stage #1: n-pentylmagnesium bromide With lithium chloride; zinc(II) chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (1′R,2′R)-2,6-bis((tert-butoxycarbonyl)oxy)-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl trifluoromethanesulfonate With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) In tetrahydrofuran at 20 - 60℃;
86%
4737-50-2

n-pentylboronic acid

C16H19BrO2

Conditions
ConditionsYield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 16h; Temperature; Suzuki Coupling; Inert atmosphere;80.7%
52154-82-2

(1R,4R)-p-mentha-2,8-dien-1-ol

78463-34-0

4,6-dibromo-5-pentylbenzene-1,3-diol

Conditions
ConditionsYield
Stage #1: (1R,4R)-p-mentha-2,8-dien-1-ol; 4,6-dibromo-5-pentylbenzene-1,3-diol With magnesium sulfate; toluene-4-sulfonic acid In dichloromethane at -20 - -15℃; Inert atmosphere;
Stage #2: With triethylamine; sodium sulfite In methanol; water for 20h; Reflux;
79%
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Chemistry

Chemistry informtion about Cannabidiol (CAS NO.13956-29-1) is:
IUPAC Name: 2-[(6r)-3-Methyl-6-Prop-1-En-2-Ylcyclohex-2-En-1-Yl]-5-Pentylbenzene-1,3-Diol
Synonyms: (-)-Trans-2-P-Mentha-1,8-Dien-3-Yl-5-Pentylresorcinol ; (-)-Trans-Cannabidiol ; ,(1r-Trans)- ; 1,3-Benzenediol, 2-[3-Methyl-6-(1-Methylethenyl)-3-Cyclohexen-1-Yl]-5-Pentyl- ; 2-(3-Methyl-6-(1-Methylethenyl)-2-Cyclohexen-1-Yl)-5-Pentyl-3-Benzenediol ; 2-(6-Isopropenyl-3-Methyl-2-Cyclohexen-1-Yl)-5-Pentyl-1,3-Benzenediol ; 8-Dien-3-Yl-5-Pentyl-2-P-Mentha-(-)-(E)-Resorcino ; Delta1(2)-Trans-Cannabidiol
Product Categories: Cannabinoid receptor 
MF: C21H30O2
MW: 314.46 
Density: 1.025 g/cm3
Flash Point: 206.3 °C
Boiling Point: 463.9 °C at 760 mmHg
Vapour Pressure: 3.14E-09 mmHg at 25°C 
Enthalpy of Vaporization: 75.31 kJ/mol
Storage temp.: 2-8°C
Following is the molecular structure of Cannabidiol (CAS NO.13956-29-1) is:

 

Uses

In April 2005, Canadian authorities approved the marketing of Sativex, a mouth spray for multiple sclerosis to alleviate pain. Sativex contains tetrahydrocannabinol together with Cannabidiol (CAS NO.13956-29-1). Initial research is showing that CBD has an effect in reducing schizophrenic symptoms in patients. Further research has verified these results. Leweke et al., (2009) performed a double blind, 4 week, explorative study controlled clinical trial, to compare the effects of purified cannabidiol and the atypical antipsychotic amisulpride on improving the symptoms of schizophrenia in 42 patients with acute schizophrenia. 'Both treatments were associated with a significant decrease of psychotic symptoms after 2 and 4 weeks as assessed by BPRS and PANSS. However, there was no statistical difference between both treatment groups. In contrast, cannabidiol induced significantly less side effects (EPS, increase in prolactin, weight gain) when compared to amisulpride'. The authors conclude cannabidiol revealed substantial antipsychotic properties in acute paranoid schizophirenia (Leweke et al., 2009). This led the authors to suggest the endocannabinoid system plays an adaptive role in the development of paranoid schizophirenia and that this research provides evidence that this mechanism may be a valuable target for 'antipsychotic treament strategies' .

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 254mg/kg (254mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 154, 1946.
monkey LD50 intravenous 212mg/kg (212mg/kg) behavioral: muscle contraction or spasticity) cardiac: arrhythmias (including changes in conduction) lungs, thorax, or respiration: dyspnea Toxicology and Applied Pharmacology. Vol. 58, Pg. 118, 1981.
mouse LD50 intravenous 50mg/kg (50mg/kg)   Journal of Medicinal Chemistry. Vol. 18, Pg. 213, 1975.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Poison by intravenous route. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes:
FlammableF
ToxicT
Risk Statements:
R11:Highly flammable. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R39/23/24/25:Toxic by inhalation, in contact with skin and if swallowed and danger of very serious irreversible effects.
Safety Statements:
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S16:Keep away from sources of ignition. 
S7:Keep container tightly closed.
RIDADR: UN 1230 3/PG 2
WGK Germany: 1
RTECS: VH1600000

Specification

Cannabidiol (CAS NO.13956-29-1) is a psychoactive cannabinoid found in Cannabis. It is a major constituent of the plant, representing up to 40% in its extracts.It is not intoxicating but displayed sedative effects in animal tests. Some research, however, indicates that CBD can increase alertness. It may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver. CBD appears to affect both the CB1 and CB2 receptors- with higher affinity for the CB2 receptors . Cannabis indica dominant strains of the plant are known to be higher in CBD than Cannabis sativa strains. Medically, it appears to relieve convulsion, inflammation, anxiety, and nausea, and to inhibit cancer cell growth. Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia.