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Chemical Product CAS:13956-29-11,3-Benzenediol,2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-

CAS:13956-29-1
1,3-Benzenediol,2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-

  • CAS No:

    13956-29-1
  • Name:

    1,3-Benzenediol,2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-
  • Molecular Formula:

    C21H30 O2
  • Molecular Weight:

    314.51
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1,3-Benzenediol,2-[(1R,6R)-3-methyl-6-(1-meth ( CASNO:13956-29-1 )

Identification and Related Records
Name:
1,3-Benzenediol,2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-
CAS Registry number:
13956-29-1
Iupac name:
2-[(1R,
6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,
3-diol
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
Molecular Formula:
C21H30 O2
Molecular Weight:
314.51
Inchi:
InChI=1/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1
InChIKey:
QHMBSVQNZZTUGM-ZWKOTPCHSA-N
Canonical SMILES:
CCCCCC1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O
Isomers smiles:
CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
Chemical and Physical Properties
Density:
1.025 g/cm3
Boiling Point:
463.9 °C at 760 mmHg
Vapour:
3.14E-09mmHg at 25°C
Refractive Index:
1.545
Flash Point:
206.3 °C
Storage temp:
2-8°C
Computed Properties:
Molecular Weight:314.4617 [g/mol]
Molecular Formula:C21H30O2
XLogP3-AA:6.5
H-Bond Donor:2
H-Bond Acceptor:2
Rotatable Bond Count:6
Tautomer Count:10
Exact Mass:314.22458
MonoIsotopic Mass:314.22458
Topological Polar Surface Area:40.5
Heavy Atom Count:23
Formal Charge:0
Complexity:414
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:2
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:2
Effective Rotor Count:6.8
Conformer Sampling RMSD:0.8
CID Conformer Count:28
Safety and Handling
Hazard Codes:
F: Flammable;T: Toxic;
Risk Statements:
R11
Safety Statements:
Poison by intravenous route. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
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.
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
Transport:
UN 1230 3
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.
Report:
EPA Genetic Toxicology Program.
Use and Manufacturing
Usage:
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' .
Biomedical Effects and Toxicity
Biological Activity:
Non-psychotropic constituent of cannabis that is anticonvulsive, antihyperalgesic and neuroprotective in vivo . GPR55 and weak CB 1 antagonist (IC 50 values are 0.445 and 3.35 μ M), CB 2 receptor inverse agonist and inhibitor of anandamide uptake (IC 50 = 27.5 μ M). Also a weak agonist at VR1 vanilloid receptors (EC 50 = 3.5 μ M).
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