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Updates including alternative names it is known by (cited). Referential simplification to phytocannabinoids (no explanation needed because the word has its own page). Links to acid derivatives, start of pharmacology section.
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'''Cannabichromene''' ('''CBC''') is one of the 120 [[cannabinoid]]s found in the ''[[Cannabis]]'' plant,<ref name=Turner2017>{{Cite book|pmid=28120231|year=2017|last1=Turner|first1=Sarah E.|first2=Claire M.|last2=Williams|first3=Leslie|last3=Iversen|authorlink3=Leslie Iversen|first4=Benjamin J.|last4=Whalley|chapter=Molecular Pharmacology of Phytocannabinoids|title=Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of ''Cannabis sativa''|editor1-first=A. Douglas|editor1-last=Kinghorn|editor2-first=Heinz|editor2-last=Falk|editor2-link=Heinz Falk|editor3-first=Simon|editor3-last=Gibbons|editor3-link=Simon Gibbons|editor4-first=Jun'ichi|editor4-last=Kobayashi|publisher=[[Springer International Publishing]]|series=Progress in the Chemistry of Organic Natural Products|volume=103|pages=61–101|doi=10.1007/978-3-319-45541-9_3|isbn=978-3-319-45539-6}}</ref> and therefore can be also described as a [[phytocannabinoid]] – from ancient Greek ''phyton'' = "plant". It bears structural similarity to the other natural cannabinoids, including [[tetrahydrocannabinol]], [[tetrahydrocannabivarin]], [[cannabidiol]], and [[cannabinol]], among others.<ref name=Turner2017/><ref name=pmid26836472>{{cite journal | first1 = Oier | last1 = Aizpurua-Olaizola | first2 = Umut | last2 = Soydaner | first3 = Ekin | last3 = Öztürk | first4 = Daniele | last4 = Schibano | first5 = Yilmaz | last5 = Simsir | first6 = Patricia | last6 = Navarro | first7 = Nestor | last7 = Etxebarria | first8 = Aresatz |last8 = Usobiaga | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = [[Journal of Natural Products]] | volume = 79 | issue = 2 | pages = 324–331 | year = 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 }}</ref> Cannabichromene and its derivatives are as abundant as [[cannabinol]]s in cannabis.<ref name=Turner2017/> It is not active at [[Cannabinoid receptor 1|CB1]] or [[Cannabinoid receptor type 2|CB2]] receptors, but is an agonist of [[TRPA1]] and less potently, an agonist of [[TRPV3]] and [[TRPV4]].<ref name=Turner2017/> CBC has two [[stereoisomers]]. It is not scheduled by the [[Convention on Psychotropic Substances]].
'''Cannabichromene''' ('''CBC'''; a.k.a. Cannabichrome; Cannanbichromene; 20675-51-8; Pentylcannabichromene; Cannabinochromene<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/cannabichromene|title=Cannabichromene|author=<!--Not stated--> |date=2019-02-04 |website=PubChem |publisher=National Center for Biotechnology Information |access-date=12 February 2019|quote=}}</ref>) is one of the 120 [[cannabinoid]]s found in the ''[[Cannabis]]'' plant,<ref name=Turner2017>{{Cite book|pmid=28120231|year=2017|last1=Turner|first1=Sarah E.|first2=Claire M.|last2=Williams|first3=Leslie|last3=Iversen|authorlink3=Leslie Iversen|first4=Benjamin J.|last4=Whalley|chapter=Molecular Pharmacology of Phytocannabinoids|title=Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of ''Cannabis sativa''|editor1-first=A. Douglas|editor1-last=Kinghorn|editor2-first=Heinz|editor2-last=Falk|editor2-link=Heinz Falk|editor3-first=Simon|editor3-last=Gibbons|editor3-link=Simon Gibbons|editor4-first=Jun'ichi|editor4-last=Kobayashi|publisher=[[Springer International Publishing]]|series=Progress in the Chemistry of Organic Natural Products|volume=103|pages=61–101|doi=10.1007/978-3-319-45541-9_3|isbn=978-3-319-45539-6}}</ref> and is therefore a [[phytocannabinoid]]. It bears structural similarity to the other natural cannabinoids, including [[tetrahydrocannabinol]] (THC), [[tetrahydrocannabivarin]] (THCV), [[cannabidiol]] (CBD), and [[cannabinol]] (CBN), among others.<ref name=Turner2017/><ref name=pmid26836472>{{cite journal | first1 = Oier | last1 = Aizpurua-Olaizola | first2 = Umut | last2 = Soydaner | first3 = Ekin | last3 = Öztürk | first4 = Daniele | last4 = Schibano | first5 = Yilmaz | last5 = Simsir | first6 = Patricia | last6 = Navarro | first7 = Nestor | last7 = Etxebarria | first8 = Aresatz |last8 = Usobiaga | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = [[Journal of Natural Products]] | volume = 79 | issue = 2 | pages = 324–331 | year = 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 }}</ref> Cannabichromene and its derivatives are as abundant as [[cannabinol]]s in cannabis.<ref name=Turner2017/> It is not active at [[Cannabinoid receptor 1|CB1]] or [[Cannabinoid receptor type 2|CB2]] receptors, but is an agonist of [[TRPA1]] and less potently, an agonist of [[TRPV3]] and [[TRPV4]].<ref name=Turner2017/> CBC has two [[stereoisomers]]. It is not scheduled by the [[Convention on Psychotropic Substances]].


== Biosynthesis ==
== Biosynthesis ==
Within the ''[[Cannabis]]'' plant, CBC occurs mainly as cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH). [[Geranyl pyrophosphate]] and [[olivetol]]ic acid combine to produce [[cannabigerol]]ic acid (a key intermediate for multiple cannabinoids), which is cyclized by the enzyme CBCA synthase to give CBCA. Over time, or when heated, CBCA is [[Decarboxylation|decarboxylated]], producing CBC. See biosynthetic scheme below the chemical data table.{{citation needed|date=January 2018}}
Within the ''[[Cannabis]]'' plant, CBC occurs mainly as [[cannabichromenic acid]] (CBCA, 2-COOH-CBC, CBC-COOH). [[Geranyl pyrophosphate]] and [[olivetol]]ic acid combine to produce [[cannabigerolic acid]] (CBGA; the sole intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated somewhere above 200° F, CBCA is [[Decarboxylation|decarboxylated]], producing CBC. See also the biosynthetic scheme image below.{{citation needed|date=January 2018}}
[[File:Biosynthesis_of_CBC.png|thumb|CBC biosynthetic scheme]]
[[File:Biosynthesis_of_CBC.png|thumb|600px|left|CBC biosynthetic scheme]]


{{-}}
==Research==
==Pharmacology==
As of 2017, CBC is under laboratory research to identify its possible [[pharmacology|pharmacological]] properties.<ref name=Turner2017/><ref>{{Cite book|pmc=5345356|year=2017|last1=Morales|first1=Paula|first2=Dow P.|last2=Hurst|first3=Patricia H.|last3=Reggio|chapter=Molecular Targets of the Phytocannabinoids: A Complex Picture|title=Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of ''Cannabis sativa''|editor1-first=A. Douglas|editor1-last=Kinghorn|editor2-first=Heinz|editor2-last=Falk|editor2-link=Heinz Falk|editor3-first=Simon|editor3-last=Gibbons|editor3-link=Simon Gibbons|editor4-first=Jun'ichi|editor4-last=Kobayashi|publisher=[[Springer International Publishing]]|series=Progress in the Chemistry of Organic Natural Products|volume=103|pages=103–131|pmid=28120232|doi=10.1007/978-3-319-45541-9_4|isbn=978-3-319-45539-6}}</ref>
As of 2017, CBC is under laboratory research to identify its possible [[pharmacology|pharmacological]] properties.<ref name=Turner2017/><ref>{{Cite book|pmc=5345356|year=2017|last1=Morales|first1=Paula|first2=Dow P.|last2=Hurst|first3=Patricia H.|last3=Reggio|chapter=Molecular Targets of the Phytocannabinoids: A Complex Picture|title=Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of ''Cannabis sativa''|editor1-first=A. Douglas|editor1-last=Kinghorn|editor2-first=Heinz|editor2-last=Falk|editor2-link=Heinz Falk|editor3-first=Simon|editor3-last=Gibbons|editor3-link=Simon Gibbons|editor4-first=Jun'ichi|editor4-last=Kobayashi|publisher=[[Springer International Publishing]]|series=Progress in the Chemistry of Organic Natural Products|volume=103|pages=103–131|pmid=28120232|doi=10.1007/978-3-319-45541-9_4|isbn=978-3-319-45539-6}}</ref>

CBC may produce an [[anti-inflammatory]] effect unique and independent of other cannabinoids in that it does not bind to [[CB1]] or [[CB2]] receptors to cause its effect. However, its effects are synergistic with at least THC (typically referred to as the "entourage effect") like other chemical constituents of [[cannabis]]. It can cause anti-edematous effects in the brain.<ref>https://www.ncbi.nlm.nih.gov/pubmed/20619971</ref> In rat


== References ==
== References ==

Revision as of 21:20, 12 February 2019

Cannabichromene
Names
IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.236.929 Edit this at Wikidata
  • InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3 ☒N
    Key: UVOLYTDXHDXWJU-UHFFFAOYSA-N ☒N
  • InChI=1/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3
    Key: UVOLYTDXHDXWJU-UHFFFAOYAG
  • CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
Properties
C21H30O2
Molar mass 314.469 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Cannabichromene (CBC; a.k.a. Cannabichrome; Cannanbichromene; 20675-51-8; Pentylcannabichromene; Cannabinochromene[1]) is one of the 120 cannabinoids found in the Cannabis plant,[2] and is therefore a phytocannabinoid. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.[2][3] Cannabichromene and its derivatives are as abundant as cannabinols in cannabis.[2] It is not active at CB1 or CB2 receptors, but is an agonist of TRPA1 and less potently, an agonist of TRPV3 and TRPV4.[2] CBC has two stereoisomers. It is not scheduled by the Convention on Psychotropic Substances.

Biosynthesis

Within the Cannabis plant, CBC occurs mainly as cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH). Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolic acid (CBGA; the sole intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated somewhere above 200° F, CBCA is decarboxylated, producing CBC. See also the biosynthetic scheme image below.[citation needed]

CBC biosynthetic scheme

Pharmacology

As of 2017, CBC is under laboratory research to identify its possible pharmacological properties.[2][4]

CBC may produce an anti-inflammatory effect unique and independent of other cannabinoids in that it does not bind to CB1 or CB2 receptors to cause its effect. However, its effects are synergistic with at least THC (typically referred to as the "entourage effect") like other chemical constituents of cannabis. It can cause anti-edematous effects in the brain.[5] In rat

References

  1. ^ "Cannabichromene". PubChem. National Center for Biotechnology Information. 2019-02-04. Retrieved 12 February 2019.
  2. ^ a b c d e Turner, Sarah E.; Williams, Claire M.; Iversen, Leslie; Whalley, Benjamin J. (2017). "Molecular Pharmacology of Phytocannabinoids". In Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Kobayashi, Jun'ichi (eds.). Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa. Progress in the Chemistry of Organic Natural Products. Vol. 103. Springer International Publishing. pp. 61–101. doi:10.1007/978-3-319-45541-9_3. ISBN 978-3-319-45539-6. PMID 28120231.
  3. ^ Aizpurua-Olaizola, Oier; Soydaner, Umut; Öztürk, Ekin; Schibano, Daniele; Simsir, Yilmaz; Navarro, Patricia; Etxebarria, Nestor; Usobiaga, Aresatz (2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products. 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. PMID 26836472.
  4. ^ Morales, Paula; Hurst, Dow P.; Reggio, Patricia H. (2017). "Molecular Targets of the Phytocannabinoids: A Complex Picture". In Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Kobayashi, Jun'ichi (eds.). Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa. Progress in the Chemistry of Organic Natural Products. Vol. 103. Springer International Publishing. pp. 103–131. doi:10.1007/978-3-319-45541-9_4. ISBN 978-3-319-45539-6. PMC 5345356. PMID 28120232.
  5. ^ https://www.ncbi.nlm.nih.gov/pubmed/20619971
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