Tetrahydrocannabutol: Difference between revisions

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{{Short description|Chemical compound}}
{{Short description|Chemical compound}}
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'''Δ<sup>9</sup>-Tetrahydrocannabutol''' ('''tetrahydrocannabinol-C4''', '''THC-C4''', '''Δ<sup>9</sup>-THCB''', '''(C4)-Δ<sup>9</sup>-THC''', '''butyl-THC''') is a [[phytocannabinoid]] found in [[Cannabis (drug)|cannabis]] that is a [[homolog (chemistry)|homologue]] of [[tetrahydrocannabinol]] (THC), the main active component of Cannabis.<ref name=":0">{{cite journal | vauthors = Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, Forni F, Gigli G, Laganà A, Montone CM, Cannazza G | title = Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal ''Cannabis sativa'' Variety: Δ<sup>9</sup>-Tetrahydrocannabutol, the Butyl Homologue of Δ<sup>9</sup>-Tetrahydrocannabinol | journal = Journal of Natural Products | volume = 83 | issue = 1 | pages = 88–98 | date = January 2020 | pmid = 31891265 | doi = 10.1021/acs.jnatprod.9b00876 | s2cid = 209519659 }}</ref> Structurally, they are only different by the [[pentyl]] [[side chain]] being replaced by a [[butyl]] side chain. THCB was studied by [[Roger Adams]] as early as 1942 <ref>{{cite journal | url=https://pubs.acs.org/doi/abs/10.1021/ja01255a061 | doi=10.1021/ja01255a061 | title=Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII<sup>1</sup> | date=1942 | last1=Adams | first1=Roger | last2=Loewe | first2=S. | last3=Smith | first3=C. M. | last4=McPhee | first4=W. D. | journal=Journal of the American Chemical Society | volume=64 | issue=3 | pages=694–697 }}</ref>
'''Δ9-Tetrahydrocannabutol''' ('''tetrahydrocannabinol-C4''', '''THC-C4''', '''Δ<sup>9</sup>-THCB''', '''(C4)-Δ<sup>9</sup>-THC''', '''butyl-THC''') is a [[homolog (chemistry)|homologue]] of [[tetrahydrocannabinol]] (THC), the active component of [[Cannabis (drug)|cannabis]].<ref name=":0">{{Cite journal|last1=Linciano|first1=Pasquale|last2=Citti|first2=Cinzia|last3=Luongo|first3=Livio|last4=Belardo|first4=Carmela|last5=Maione|first5=Sabatino|last6=Vandelli|first6=Maria Angela|last7=Forni|first7=Flavio|last8=Gigli|first8=Giuseppe|last9=Laganà|first9=Aldo|last10=Montone|first10=Carmela Maria|last11=Cannazza|first11=Giuseppe|date=2020-01-24|title=Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ 9 -Tetrahydrocannabutol, the Butyl Homologue of Δ 9 -Tetrahydrocannabinol|url=https://pubs.acs.org/doi/10.1021/acs.jnatprod.9b00876|journal=Journal of Natural Products|language=en|volume=83|issue=1|pages=88–98|doi=10.1021/acs.jnatprod.9b00876|pmid=31891265|s2cid=209519659|issn=0163-3864}}</ref> They are only different by the [[pentyl]] [[side chain]] being replaced by a [[butyl]] side chain. Δ9-THCB, showed an affinity for the human CB1 (''K''i = 15 nM) and CB2 receptors (''K''i = 51 nM) comparable to that of Δ9-THC.<ref name=":0" /> The formalin test in vivo was performed on Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties.<ref name=":0" /> The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor.<ref name=":0" /> The [[propyl]] analog, [[THCV]], is a [[cannabinoid receptor type 1]] and [[cannabinoid receptor type 2]] antagonist,<ref>{{cite journal | vauthors = Thomas A, Stevenson LA, Wease KN, Price MR, Baillie G, Ross RA, Pertwee RG | title = Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist | journal = British Journal of Pharmacology | volume = 146 | issue = 7 | pages = 917–26 | date = December 2005 | pmid = 16205722 | pmc = 1751228 | doi = 10.1038/sj.bjp.0706414 }}</ref> while THC is a CB<sub>1</sub> agonist. THCB has rarely been isolated from cannabis samples,<ref name=":0" /><ref>{{cite journal | vauthors = Harvey DJ | title = Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry | journal = The Journal of Pharmacy and Pharmacology | volume = 28 | issue = 4 | pages = 280–5 | date = April 1976 | pmid = 6715 | doi = 10.1111/j.2042-7158.1976.tb04153.x | s2cid = 32734030 }}</ref> but appears to be less commonly present than THC or THCV. It is metabolised in a similar manner to THC.<ref>{{cite journal | vauthors = Brown NK, Harvey DJ | title = In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 18 | issue = 4 | pages = 417–27 | date = April 1988 | pmid = 2840781 | doi = 10.3109/00498258809041678 }}</ref> Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.<ref>{{cite web |title=Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie? |url=http://www.dutch-headshop.com/nl/verschil-thc-olie-cannabisolie-cbd-olie-wietolie-hennepolie-a-176.html |website=Dutch-Headshop.com |access-date=19 November 2016 }}</ref> The Δ<sup>8</sup> isomer is known as a synthetic cannabinoid under the code name '''JWH-130''',<ref name="pmid27398024">{{cite journal | vauthors = Bow EW, Rimoldi JM | title = The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation | journal = Perspectives in Medicinal Chemistry | volume = 8 | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> and the ring-opened analogue '''cannibidibutol''' is also known.<ref name="pmid27722705">{{cite journal | vauthors = Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G | title = Phytocannabinoids: a unified critical inventory | journal = Natural Product Reports | volume = 33 | issue = 12 | pages = 1357–1392 | date = November 2016 | pmid = 27722705 | doi = 10.1039/c6np00074f }}</ref>

⚫
[[File:Cannabidibutol_structure.png|220px|thumb|left|Cannabidibutol (CBDB), 60113-11-3 [https://pubchem.ncbi.nlm.nih.gov/compound/59444413]]]{{clear-left}}
== Pharmacology ==
⚫
[[File:JWH-130_structure.png|220px|thumb|left|JWH-130 (Δ<sup>8</sup>-THCB), 51768-59-3 [https://pubchem.ncbi.nlm.nih.gov/compound/6452496]]]{{clear-left}}

Δ<sup>9</sup>-THCB, showed an affinity for the human CB<sub>1</sub> (''K''i = 15 nM) and CB<sub>2</sub> receptors (''K''i = 51 nM) comparable to that of Δ<sup>9</sup>-THC.<ref name=":0" /> The formalin test in vivo was performed on Δ<sup>9</sup>-THCB in order to reveal possible analgesic and anti-inflammatory properties.<ref name=":0" /> The tetrad test in mice showed a partial agonistic activity of Δ<sup>9</sup>-THCB toward the CB<sub>1</sub> receptor.<ref name=":0" /> THCB has rarely been isolated from cannabis samples,<ref name=":0" /><ref>{{cite journal | vauthors = Harvey DJ | title = Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry | journal = The Journal of Pharmacy and Pharmacology | volume = 28 | issue = 4 | pages = 280–285 | date = April 1976 | pmid = 6715 | doi = 10.1111/j.2042-7158.1976.tb04153.x | s2cid = 32734030 }}</ref> but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.<ref>{{cite journal | vauthors = Brown NK, Harvey DJ | title = In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 18 | issue = 4 | pages = 417–427 | date = April 1988 | pmid = 2840781 | doi = 10.3109/00498258809041678 }}</ref>

In an analysis by the [[University of Rhode Island]] on [[phytocannabinoids]] it was found that THC-Butyl had the highest [[3C-like protease]] inhibitor activity against [[COVID-19]] out of all the phytocannabinoids tested within that study but not as high as the [[antiviral drug]] [[GC376]] (81% THCB vs. 100% GC376).<ref>{{cite journal | vauthors = Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H | title = Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity | journal = Molecules | volume = 27 | issue = 18 | page = 6127 | date = September 2022 | pmid = 36144858 | doi = 10.3390/molecules27186127 | pmc = 9502466 | doi-access = free }}</ref>

== Chemistry ==
Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.<ref>{{cite web |title=Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie? |url=http://www.dutch-headshop.com/nl/verschil-thc-olie-cannabisolie-cbd-olie-wietolie-hennepolie-a-176.html |website=Dutch-Headshop.com |access-date=19 November 2016 }}</ref> The Δ<sup>8</sup> isomer is known as a synthetic cannabinoid under the code name '''JWH-130''',<ref name="pmid27398024">{{cite journal | vauthors = Bow EW, Rimoldi JM | title = The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation | journal = Perspectives in Medicinal Chemistry | volume = 8 | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> and the ring-opened analogue '''cannibidibutol''' ('''CBDB''') is also known.<ref name="pmid27722705">{{cite journal | vauthors = Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G | title = Phytocannabinoids: a unified critical inventory | journal = Natural Product Reports | volume = 33 | issue = 12 | pages = 1357–1392 | date = November 2016 | pmid = 27722705 | doi = 10.1039/c6np00074f | doi-access = free }}</ref> THC-Butyl can be synthesized from [[4-butylresorcinol]].{{cn|date=March 2024}}
⚫
[[File:Cannabidibutol_structure.png|220px|thumb|left|Cannabidibutol (CBDB), 60113-11-3 [https://pubchem.ncbi.nlm.nih.gov/compound/59444413]]]{{clear left}}
⚫
[[File:JWH-130_structure.png|220px|thumb|left|JWH-130 (Δ<sup>8</sup>-THCB), 51768-59-3 [https://pubchem.ncbi.nlm.nih.gov/compound/6452496]]]{{clear left}}


==Legality==
==Legality==
Line 52: Line 62:
* ''[[Cannabis]]''
* ''[[Cannabis]]''
* [[Cannabinoid]]
* [[Cannabinoid]]
* [[Hexahydrocannabutol]]
* [[Parahexyl]]
* [[Parahexyl]]
* [[Perrottetinene]]
* [[Perrottetinene]]

Latest revision as of 18:33, 31 March 2024

Δ9-Tetrahydrocannabinol-C4
Clinical data
ATC code
  • none
Identifiers
  • (−)-(6aR,10aR)-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
  • CCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)O
  • InChI=1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1 ☒N
  • Key:QHCQSGYWGBDSIY-HZPDHXFCSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Δ9-Tetrahydrocannabutol (tetrahydrocannabinol-C4, THC-C4, Δ9-THCB, (C4)-Δ9-THC, butyl-THC) is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis.[1] Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942 [2]

Pharmacology[edit]

Δ9-THCB, showed an affinity for the human CB1 (Ki = 15 nM) and CB2 receptors (Ki = 51 nM) comparable to that of Δ9-THC.[1] The formalin test in vivo was performed on Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties.[1] The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor.[1] THCB has rarely been isolated from cannabis samples,[1][3] but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.[4]

In an analysis by the University of Rhode Island on phytocannabinoids it was found that THC-Butyl had the highest 3C-like protease inhibitor activity against COVID-19 out of all the phytocannabinoids tested within that study but not as high as the antiviral drug GC376 (81% THCB vs. 100% GC376).[5]

Chemistry[edit]

Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.[6] The Δ8 isomer is known as a synthetic cannabinoid under the code name JWH-130,[7] and the ring-opened analogue cannibidibutol (CBDB) is also known.[8] THC-Butyl can be synthesized from 4-butylresorcinol.[citation needed]

Cannabidibutol (CBDB), 60113-11-3 [1]
JWH-130 (Δ8-THCB), 51768-59-3 [2]

Legality[edit]

THCB is not scheduled internationally under the Convention on Psychotropic Substances, but may be controlled under analogue law in some individual jurisdictions as a homologue of THC.

See also[edit]

References[edit]

  1. ^ a b c d e Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, et al. (January 2020). "Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ9-Tetrahydrocannabutol, the Butyl Homologue of Δ9-Tetrahydrocannabinol". Journal of Natural Products. 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. PMID 31891265. S2CID 209519659.
  2. ^ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
  3. ^ Harvey DJ (April 1976). "Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry". The Journal of Pharmacy and Pharmacology. 28 (4): 280–285. doi:10.1111/j.2042-7158.1976.tb04153.x. PMID 6715. S2CID 32734030.
  4. ^ Brown NK, Harvey DJ (April 1988). "In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 18 (4): 417–427. doi:10.3109/00498258809041678. PMID 2840781.
  5. ^ Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H (September 2022). "Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity". Molecules. 27 (18): 6127. doi:10.3390/molecules27186127. PMC 9502466. PMID 36144858.
  6. ^ "Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie?". Dutch-Headshop.com. Retrieved 19 November 2016.
  7. ^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC 4927043. PMID 27398024.
  8. ^ Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G (November 2016). "Phytocannabinoids: a unified critical inventory". Natural Product Reports. 33 (12): 1357–1392. doi:10.1039/c6np00074f. PMID 27722705.
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