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Chemistry

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Also known as: 13956-29-1, (-)-cannabidiol, (-)-trans-cannabidiol, Epidiolex, Cbd, (-)-cbd
Molecular Formula
C21H30O2
Molecular Weight
314.5  g/mol
InChI Key
QHMBSVQNZZTUGM-ZWKOTPCHSA-N
FDA UNII
19GBJ60SN5

Cannabidiol
Compound isolated from Cannabis sativa extract.
The mechanism of action of cannabidiol is as a Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C9 Inhibitor, and Cytochrome P450 2C19 Inhibitor, and UGT1A9 Inhibitor, and UGT2B7 Inhibitor, and Cytochrome P450 1A2 Inhibitor, and Cytochrome P450 2B6 Inhibitor, and Cytochrome P450 2B6 Inducer.
1 2D Structure

Cannabidiol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
2.1.2 InChI
InChI=1S/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
2.1.3 InChI Key
QHMBSVQNZZTUGM-ZWKOTPCHSA-N
2.1.4 Canonical SMILES
CCCCCC1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O
2.1.5 Isomeric SMILES
CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
2.2 Other Identifiers
2.2.1 UNII
19GBJ60SN5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,3-benzenediol, 2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, (1r-trans)-

2. Epidiolex

2.3.2 Depositor-Supplied Synonyms

1. 13956-29-1

2. (-)-cannabidiol

3. (-)-trans-cannabidiol

4. Epidiolex

5. Cbd

6. (-)-cbd

7. Gwp42003-p

8. Cannabidiol [usan]

9. (-)-trans-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol

10. Delta1(2)-trans-cannabidiol

11. 2-[(1r,6r)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

12. 19gbj60sn5

13. Chembl190461

14. 3556-78-3

15. .delta.1(2)-trans-cannabidiol

16. Chebi:69478

17. Btx-1204

18. Btx-1503

19. Gwp42003

20. Gwp-42003-p

21. Gwp-42003

22. Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, (-)-(e)-

23. 2-[1r-3-methyl-6r-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol

24. C21h30o2

25. 1,3-benzenediol, 2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, (1r-trans)-

26. 2-((1r,6r)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol

27. (1'r,2'r)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydrobiphenyl-2,6-diol

28. Cannabidiol Solution

29. 2-[(1r,6r)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol

30. (-)-cannabidiol (cbd)

31. Cannabidiolum

32. Unii-19gbj60sn5

33. 1,3-benzenediol, 2-[(1r,6r)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-

34. 1,3-benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, (1r-trans)-

35. Epidiolex (tn)

36. 1,3-benzenediol, 2-((1r,6r)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-

37. P0t

38. Cannabidiol (7ci)

39. Cardiolrx

40. (+/-)-cannabidiol

41. Cannabidiol [mi]

42. Cannabidiol [inn]

43. Cannabidiol (usan/inn)

44. D1(2)-trans-cannabidiol

45. Cannabidiol [inci]

46. Cannabidiol [mart.]

47. Cannabidiol [usp-rs]

48. Cannabidiol [who-dd]

49. (-)-cannabidiol (synthetic)

50. Schembl119679

51. Gtpl4150

52. Zyn002

53. 2-(6-isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol #

54. 2-(6-isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol

55. Delta(1(2))-trans-cannabidiol

56. Cannabidiol [orange Book]

57. Dtxsid00871959

58. Dtxsid301038839

59. Zinc4097406

60. Bdbm50121429

61. Bdbm50318484

62. Cannabidiol Solution [usp-rs]

63. Akos032948358

64. Db09061

65. Ncgc00386518-01

66. (-)-cannabidiol 1.0 Mg/ml In Methanol

67. Ac-34022

68. Db-093531

69. Sativex (cbd + Thc, Fixed-dose Oral Spray)

70. C07578

71. D10915

72. Nabiximols (cbd + Thc, Fixed-dose Oral Spray)

73. Q422917

74. (-)-cannabidiol (cbd) 100 Microg/ml In Methanol

75. (-)-cannabidiol (cbd) 1000 Microg/ml In Methanol

76. (-)-cannabidiol (cbd) 250 Microg/ml In Acetonitrile

77. (3r,4r)-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol

78. Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, (+-)-

79. Resorcinol, 2-p-mentha-1,8-dien-3-yl-5-pentyl-, Trans-(-)- (8ci)

80. 1,3-benzenediol, 2-(4-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, Trans-

81. 2-((1r,6r)-3-methyl-6-(1-methylethenyl)cyclohex-2-enyl)-5-pentylbenzene-1,3-diol

82. 2-(3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol

83. 2-(4-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Trans-

84. 2-(6-isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol (cannabidiol)

85. 2-[(1r,6r)-3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl]-5-pentylbenzene-1,3-diol

86. 2-[3-methyl-6-(methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol

87. Cannabidiol Solution, ~10 Mg/ml In Ethanol, Analytical Standard, For Drug Analysis

88. Cannabidiol Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

89. Cannabidiol Solution, 1.0 Mg/ml In Methanol, Analytical Standard, For Drug Analysis

90. (1'r,2'r)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol

91. (1'r,2'r)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro[1,1'-biphenyl]-2,6-diol

92. 2-((1r,6r)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol

2.4 Create Date
2005-06-08
3 Chemical and Physical Properties
Molecular Weight 314.5 g/mol
Molecular Formula C21H30O2
XLogP36.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass314.224580195 g/mol
Monoisotopic Mass314.224580195 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count23
Formal Charge0
Complexity414
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

When used in combination with delta-9-tetrahydrocannabinol as the product Sativex, cannabidiol was given a standard marketing authorization (ie. a Notice of Compliance (NOC)) by Health Canada for the following indications: 1) as adjunctive treatment for symptomatic relief of spasticity in adult patients with multiple sclerosis (MS) who have not responded adequately to other therapy and who demonstrate meaningful improvement during an initial trial of therapy; Due to the need for confirmatory studies to verify the clinical benefit coupled with the promising nature of the clinical evidence, Sativex was also given a Notice of Compliance with Conditions (NOC/c) by Health Canada for the following indications: 1) as adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis; 2) as adjunctive analgesic treatment in adult patients with advanced cancer who experience moderate to severe pain during the highest tolerated dose of strong opioid therapy for persistent background pain.


Epidyolex is indicated for use as adjunctive therapy of seizures associated with Lennox Gastaut syndrome (LGS) or Dravet syndrome (DS), in conjunction with clobazam, for patients 2 years of age and older.


Treatment of Rett syndrome


Treatment of seizures associated with Dravet Syndrome (DS), Treatment of seizures associated with infantile spasms (IS), Treatment of seizures associated with Lennox-Gastaut Syndrome (LGS), Treatment of seizures associated with Tuberous Sclerosis Complex (TSC)


5 Pharmacology and Biochemistry
5.1 Pharmacology

Although the exact mechanism and magnitude of effects of THC and CBD are not fully understood, CBD has been shown to have analgesic, anticonvulsant, muscle relaxant, anxiolytic, neuroprotective, anti-oxidant, and anti-psychotic activity. This wide variety of effects is likely due to it's complex pharmacological mechanisms. In addition to binding to CB1 and CB2 receptors of the endocannabinoid system, there is evidence that CBD activates 5-HT1A serotonergic and TRPV12 vanilloid receptors, antagonizes alpha-1 adrenergic and -opioid receptors, inhibits synaptosomal uptake of noradrenaline, dopamine, serotonin and gaminobutyric acid and cellular uptake of anandamide, acts on mitochondria Ca2 stores, blocks low-voltage-activated (T-type) Ca2 channels, stimulates activity of the inhibitory glycine-receptor, and inhibits activity of fatty amide hydrolase (FAAH).


5.2 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CANNABIDIOL
5.3.2 FDA UNII
19GBJ60SN5
5.3.3 Pharmacological Classes
Cytochrome P450 1A2 Inhibitors [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 2B6 Inhibitors [MoA]; Cytochrome P450 2C19 Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]; UGT1A9 Inhibitors [MoA]; UGT2B7 Inhibitors [MoA]; Cannabinoids [CS]
5.4 ATC Code

N03AX


N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AX - Other antiepileptics

N03AX24 - Cannabidiol


5.5 Absorption, Distribution and Excretion

Absorption

Following a single buccal administration, maximum plasma concentrations of both CBD and THC typically occur within two to four hours. When administered buccally, blood levels of THC and other cannabinoids are lower compared with inhalation of smoked cannabis. The resultant concentrations in the blood are lower than those obtained by inhaling the same dose because absorption is slower, redistribution into fatty tissues is rapid and additionally some of the THC undergoes hepatic first pass metabolism to 11-OH-THC, a psycho-active metabolite. The CBD component of sublingual Sativex was found to have a Tmax of 1.63hr and a Cmax of 2.50ng/mL, while buccal Sativex was found to have a Tmax of 2.80hr and a Cmax of 3.02ng/mL.


Route of Elimination

Elimination from plasma is bi-exponential with an initial half-life of one to two hours. The terminal elimination half-lives are of the order of 24 to 36 hours or longer. Sativex is excreted in the urine and faeces.


Volume of Distribution

Cannabinoids are distributed throughout the body; they are highly lipid soluble and accumulate in fatty tissue. The release of cannabinoids from fatty tissue is responsible for the prolonged terminal elimination half-life.


5.6 Metabolism/Metabolites

THC and CBD are metabolized in the liver by a number of cytochrome P450 isoenzymes, including CYP2C9, CYP2C19, CYP2D6 and CYP3A4. They may be stored for as long as four weeks in the fatty tissues from which they are slowly released at sub-therapeutic levels back into the blood stream and metabolized via the renal and biliary systems. The main primary metabolite of CBD is 7-hydroxy-cannabidiol.


5.7 Biological Half-Life

The CBD component of sublingual Sativex was found to have a half life (t1/2) of 1.44hr, while buccal Sativex was found to have a half life (t1/2) of 1.81hr.


5.8 Mechanism of Action

The exact mechanism of action of CBD and THC is not currently fully understood. However, it is known that CBD acts on cannabinoid (CB) receptors of the endocannabinoid system, which are found in numerous areas of the body, including the peripheral and central nervous systems, including the brain. The endocannabinoid system regulates many physiological responses of the body including pain, memory, appetite, and mood. More specifically, CB1 receptors can be found within the pain pathways of the brain and spinal cord where they may affect CBD-induced analgesia and anxiolysis, and CB2 receptors have an effect on immune cells, where they may affect CBD-induced anti-inflammatory processes. CBD has been shown to act as a negative allosteric modulator of the cannabinoid CB1 receptor, the most abundant G-Protein Coupled Receptor (GPCR) in the body. Allosteric regulation of a receptor is achieved through the modulation of the activity of a receptor on a functionally distinct site from the agonist or antagonist binding site. The negative allosteric modulatory effects of CBD are therapeutically important as direct agonists are limited by their psychomimetic effects while direct antagonists are limited by their depressant effects.


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09-Mar-2022
02-Jul-2024
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