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'''Δ9-Tetrahydrocannabutol''', '''tetrahydrocannabinol-C4''', '''THC-C4''', '''Δ<sup>9</sup>-THCB''', '''(C4)-Δ<sup>9</sup>-THC''', or '''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|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>
'''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|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>


==Legality==
==Legality==

Revision as of 08:53, 28 September 2021

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
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 homologue of tetrahydrocannabinol (THC), the active component of cannabis.[1] 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 (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] The propyl analog, THCV, is a cannabinoid receptor type 1 and cannabinoid receptor type 2 antagonist,[2] while THC is a CB1 agonist. THCB has rarely been isolated from cannabis samples,[1][3] but appears to be less commonly present than THC or THCV. It is metabolised in a similar manner to THC.[4] Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.[5] The Δ8 isomer is known as a synthetic cannabinoid under the code name JWH-130.[6]

Legality

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

References

  1. ^ a b c d e Linciano, Pasquale; Citti, Cinzia; Luongo, Livio; Belardo, Carmela; Maione, Sabatino; Vandelli, Maria Angela; Forni, Flavio; Gigli, Giuseppe; Laganà, Aldo; Montone, Carmela Maria; Cannazza, Giuseppe (2020-01-24). "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". Journal of Natural Products. 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. ISSN 0163-3864. PMID 31891265.
  2. ^ Thomas A, Stevenson LA, Wease KN, Price MR, Baillie G, Ross RA, Pertwee RG (December 2005). "Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist". British Journal of Pharmacology. 146 (7): 917–26. doi:10.1038/sj.bjp.0706414. PMC 1751228. PMID 16205722.
  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): 280–5. 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): 417–27. doi:10.3109/00498258809041678. PMID 2840781.
  5. ^ "Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie?". Dutch-Headshop.com. Retrieved 19 November 2016.
  6. ^ 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.
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