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{{Short description|Chemical compound}}
{{Short description|Cannabinoid agonist compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Distinguish|Tetrakis(hydroxymethyl)phosphonium chloride{{!}}Tetrakis(hydroxymethyl)phosphonium chloride (THPC)}}
{{Distinguish|Tetrakis(hydroxymethyl)phosphonium chloride{{!}}Tetrakis(hydroxymethyl)phosphonium chloride (THPC)}}
{{Seealso|Cannabidiphorol{{!}}Cannabidiphorol (CBDP)}}
{{See also|Cannabidiphorol{{!}}Cannabidiphorol (CBDP)}}
{{More citations needed|date=September 2022}}
{{More citations needed|date=September 2022}}


{{Infobox drug
{{Drugbox
| synonyms = (-)-Trans-Δ<sup>9</sup>-tetrahydrocannabiphorol<br />Δ<sup>9</sup>-THCP<br />(C7)-Δ<sup>9</sup>-THC<br />THC-Heptyl
| synonyms = (-)-Trans-Δ<sup>9</sup>-tetrahydrocannabiphorol<br />Δ<sup>9</sup>-THCP<br />(C7)-Δ<sup>9</sup>-THC<br />THC-Heptyl
| IUPAC_name = (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
| IUPAC_name = (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
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}}
}}


'''Tetrahydrocannabiphorol''' ('''THCP''') is a potent [[phytocannabinoid]], a [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]] [[agonist]] which was known as a synthetic homologue of [[tetrahydrocannabinol|THC]],<ref name="pmid2992174">{{cite journal | vauthors = Harvey DJ | title = Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 15 | issue = 3 | pages = 187–197 | date = March 1985 | pmid = 2992174 | doi = 10.3109/00498258509045349 }}</ref> but for the first time in 2019 was isolated as a [[natural product]] in trace amounts from ''[[Cannabis sativa]]''.<ref>{{cite journal | vauthors = Bueno J, Greenbaum EA | title = (-)-<i>trans</i>-Δ<sup>9</sup>-Tetrahydrocannabiphorol Content of <i>Cannabis sativa</i> Inflorescence from Various Chemotypes | journal = Journal of Natural Products | volume = 84 | issue = 2 | pages = 531–536 | date = February 2021 | pmid = 33565878 | doi = 10.1021/acs.jnatprod.0c01034 | s2cid = 231866062 }}</ref><ref>{{cite journal | vauthors = Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, Pecchioni N, Vandelli MA, Laganà A, Capriotti AL, Biagini G, Carbone L, Gigli G, Cannazza G | display-authors = 6 | title = The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions | journal = Talanta | volume = 235 | pages = 122704 | date = December 2021 | pmid = 34517579 | doi = 10.1016/j.talanta.2021.122704 | hdl = 11380/1250339 | hdl-access = free }}</ref> It is structurally similar to Δ<sup>9</sup>-[[tetrahydrocannabinol|THC]], the main active component of cannabis, but with the [[pentyl]] side chain extended to [[heptyl]]. Since it has a longer side chain, its [[cannabinoid]] effects are "far higher than Δ<sup>9</sup>-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2nM at CB1, approximately 33 times that of Delta-9-THC (40nM at CB1).<ref>{{cite web|title=THCp and CBDp, Newly Discovered, Extremely Potent Cannabinoids|date=29 June 2020|url=https://acslabcannabis.com/blog/cannabinoids/thcp-and-cbdp-newly-discovered-extremely-potent-cannabinoids/}}</ref>
'''Tetrahydrocannabiphorol''' ('''THCP''') is a potent [[phytocannabinoid]], a [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]] [[agonist]] which was known as a synthetic homologue of [[tetrahydrocannabinol|THC]],<ref name="pmid2992174">{{cite journal | vauthors = Harvey DJ | title = Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 15 | issue = 3 | pages = 187–197 | date = March 1985 | pmid = 2992174 | doi = 10.3109/00498258509045349 }}</ref> but for the first time in 2019 was isolated as a [[natural product]] in trace amounts from ''[[Cannabis sativa]]''.<ref name="Bueno Greenbaum 2021">{{cite journal | vauthors = Bueno J, Greenbaum EA | title = (-)-''trans''-Δ<sup>9</sup>-Tetrahydrocannabiphorol Content of ''Cannabis sativa'' Inflorescence from Various Chemotypes | journal = Journal of Natural Products | volume = 84 | issue = 2 | pages = 531–536 | date = February 2021 | pmid = 33565878 | doi = 10.1021/acs.jnatprod.0c01034 | s2cid = 231866062 }}</ref><ref>{{cite journal | vauthors = Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, Pecchioni N, Vandelli MA, Laganà A, Capriotti AL, Biagini G, Carbone L, Gigli G, Cannazza G | title = The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions | journal = Talanta | volume = 235 | pages = 122704 | date = December 2021 | pmid = 34517579 | doi = 10.1016/j.talanta.2021.122704 | hdl-access = free | hdl = 11380/1250339 }}</ref> It is structurally similar to Δ<sup>9</sup>-[[tetrahydrocannabinol|THC]], the main active component of cannabis, but with the [[pentyl]] side chain extended to [[heptyl]]. Since it has a longer side chain, its [[cannabinoid]] effects are "far higher than Δ<sup>9</sup>-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2&nbsp;nM at CB<sub>1</sub>, approximately 33 times that of Δ<sup>9</sup>-THC (40&nbsp;nM at CB<sub>1</sub>).<ref name="Citti et al 2019">{{cite journal | vauthors = Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, Laganà A, Capriotti AL, Forni F, Vandelli MA, Gigli G, Cannazza G | title = A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ<sup>9</sup>-tetrahydrocannabinol: Δ<sup>9</sup>-Tetrahydrocannabiphorol | journal = Scientific Reports | volume = 9 | issue = 1 | pages = 20335 | date = December 2019 | pmid = 31889124 | pmc = 6937300 | doi = 10.1038/s41598-019-56785-1 | bibcode = 2019NatSR...920335C }}</ref>

THCP 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 | vauthors = Adams R, Loewe S, Smith CM, McPhee WD | journal=Journal of the American Chemical Society | volume=64 | issue=3 | pages=694–697 }}</ref>


==Isomers==
==Isomers==
===Delta-3-THCP===
===Delta-3-THCP===
[[File:D3-THCP_structure.png|220px|thumb|left|Δ<sup>3</sup>-THCP [https://pubchem.ncbi.nlm.nih.gov/compound/162224085]]]
[[File:D3-THCP_structure.png|220px|thumb|left|Δ<sup>3</sup>-THCP [https://pubchem.ncbi.nlm.nih.gov/compound/162224085]]]
{{clear-left}}
{{clear left}}


The Δ<sup>3</sup>/Δ<sup>6a(10a)</sup> isomer Δ<sup>3</sup>-THCP was synthesised in 1941, and was found to have around the same potency as [[Delta-3-Tetrahydrocannabinol|Δ<sup>3</sup>-THC]], unlike the hexyl homologue [[parahexyl]] which was significantly stronger.<ref>{{cite journal | vauthors = Adams R, Loewe S, Jelinek C, Wolff H | title = Tetrahydrocannabinol Homologs with Marihuana Activity. IX. | journal = Journal of the American Chemical Society | date = July 1941 | volume = 63 | issue = 7 | pages = 1971–1973 | doi = 10.1021/ja01852a052 }}</ref>
The Δ<sup>3</sup>/Δ<sup>6a(10a)</sup> isomer Δ<sup>3</sup>-THCP was synthesised in 1941, and was found to have around the same potency as [[Delta-3-Tetrahydrocannabinol|Δ<sup>3</sup>-THC]], unlike the hexyl homologue [[parahexyl]] which was significantly stronger.<ref>{{cite journal | vauthors = Adams R, Loewe S, Jelinek C, Wolff H | title = Tetrahydrocannabinol Homologs with Marihuana Activity. IX. | journal = Journal of the American Chemical Society | date = July 1941 | volume = 63 | issue = 7 | pages = 1971–1973 | doi = 10.1021/ja01852a052 }}</ref>


===Delta-8-THCP===
===Delta-8-THCP===
[[File:JWH-091_structure.png|220px|thumb|left|JWH-091 (Δ<sup>8</sup>-THCP) [https://pubchem.ncbi.nlm.nih.gov/compound/44307335], CAS# 51768-60-6]]
[[File:JWH-091_structure.png|220px|thumb|left|JWH-091 (Δ<sup>8</sup>-THCP) [https://pubchem.ncbi.nlm.nih.gov/compound/44307335], CAS# 51768-60-6]]
{{clear-left}}
{{clear left}}


The Δ<sup>8</sup> isomer is also known as a [[synthetic cannabinoid]] under the code name '''JWH-091'''.<ref name="pmid10454479">{{cite journal | vauthors = Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK | display-authors = 6 | title = Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 3 | pages = 1065–1079 | date = September 1999 | pmid = 10454479 | url = https://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10454479 }}</ref><ref name="Bow_2016">{{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 | issue = | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> It's unconfirmed whether or not Delta-8-THCP is found naturally in cannabis plants, but likely is due to Delta-8-THC itself being a degraded form of Delta-9-THC. <ref>{{Cite book|chapter-url=https://doi.org/10.1016/B978-008045382-8.00091-5|doi=10.1016/B978-008045382-8.00091-5|chapter=Chemistry of Cannabis|title=Comprehensive Natural Products II|year=2010| vauthors = Hazekamp A, Fischedick JT, Díez ML, Lubbe A, Ruhaak RL |pages=1033–1084|isbn=978-0-08-045382-8 }}</ref> JWH-091 has approximately double the binding affinity at the CB1 receptor (22nM ± 3.9nM) in comparison to Delta-9-THC (40.7nM ± 1.7nM) or Delta-8-THC (44nM ± 12nM),<ref name="Bow_2016" /> but appears significantly lower in vitro than the binding activity of Delta-9-THCP (Ki = 1.2 nM CB1)<ref name="Citti_2019">{{cite journal | vauthors = Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, Laganà A, Capriotti AL, Forni F, Vandelli MA, Gigli G, Cannazza G | display-authors = 6 | title = A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ<sup>9</sup>-tetrahydrocannabinol: Δ<sup>9</sup>-Tetrahydrocannabiphorol | journal = Scientific Reports | volume = 9 | issue = 1 | pages = 20335 | date = December 2019 | pmid = 31889124 | pmc = 6937300 | doi = 10.1038/s41598-019-56785-1 | bibcode = 2019NatSR...920335C | doi-access = free }}</ref>
The Δ<sup>8</sup> isomer is also known as a [[synthetic cannabinoid]] under the code name '''JWH-091'''.<ref name="pmid10454479">{{cite journal | vauthors = Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK | title = Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 3 | pages = 1065–1079 | date = September 1999 | pmid = 10454479 | url = https://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10454479 }}</ref><ref name="Bow_2016">{{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 | issue = | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> It's unconfirmed whether or not Δ<sup>8</sup>-THCP is found naturally in cannabis plants, but likely is due to Δ<sup>8</sup>-THC itself being a degraded form of Δ<sup>9</sup>-THC.<ref>{{cite book |doi=10.1016/B978-008045382-8.00091-5 |chapter=Chemistry of Cannabis |title=Comprehensive Natural Products II |date=2010 | vauthors = Hazekamp A, Fischedick JT, Díez ML, Lubbe A, Ruhaak RL |pages=1033–1084 |isbn=978-0-08-045382-8 |chapter-url=https://books.google.com/books?id=ISBN9780080453828&pg=PA1033 }}</ref> JWH-091 has approximately double the binding affinity at the CB<sub>1</sub> receptor (22&nbsp;nM&nbsp;±&nbsp;3.9&nbsp;nM) in comparison to Δ<sup>9</sup>-THC (40.7&nbsp;nM&nbsp;±&nbsp;1.7&nbsp;nM) or Δ<sup>8</sup>-THC (44&nbsp;nM&nbsp;±&nbsp;12&nbsp;nM),<ref name="Bow_2016" /> but appears significantly lower in vitro than the binding activity of Δ<sup>9</sup>-THCP (K<sub>i</sub> = 1.2&nbsp;nM)<ref name="Citti et al 2019"/>


== Natural occurrence in Cannabis ==
== Natural occurrence in cannabis ==
Delta-9-THCP occurs naturally in Cannabis but in small amounts, an analysis on mid to high THC strains ranged approximately from 0.0023% to 0.0136% (w/w) (approximately 0.02mg-0.13mg per gram) with no correlation with THC percentage, such a strain with 8% THC vs 20% THC both with similar amounts of THCP.<ref>https://pubs.acs.org/doi/full/10.1021/acs.jnatprod.0c01034</ref>
The Δ<sup>9</sup> isomer of THCP occurs naturally in [[Cannabis sativa|cannabis]], but in small amounts. A 2021 study reported the content of Δ<sup>9</sup>-THCP ranging from 0.0023% to 0.0136% (w/w) (approximately 0.02–0.13&nbsp;mg/g) without correlation to THC percentage in [[Δ-9-Tetrahydrocannabinol|Δ<sup>9</sup>-THC]]-dominant strains of cannabis; that study failed to detect THCP in [[Cannabidiol|CBD]]-dominant strains.<ref name="Bueno Greenbaum 2021"/><ref>{{cite journal|url=https://pubmed.ncbi.nlm.nih.gov/33565878|title=(-)- trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes|date=2021 |pmid=33565878 |access-date=19 Feb 2024 |journal=Journal of Natural Products |volume=84 |issue=2 |pages=531–536 |doi=10.1021/acs.jnatprod.0c01034 |s2cid=231866062 | vauthors = Bueno J, Greenbaum EA }}</ref>


== See also ==
== See also ==
* [[CBD-DMH]]
* [[Nabilone]]
⚫
* [[Hexahydrocannabiphorol]]
* [[1,2-Didehydro-3-oxo-THCO]]
* [[Delta-8-THC]]
* [[Delta-8-THC]]
* [[Hexahydrocannabinol]]
⚫
* [[Hexahydrocannabiphorol]]
* [[HU-210]]
* [[JWH-138]]
* [[Parahexyl]]
* [[Parahexyl]]
* [[Perrottetinene]]
* [[Perrottetinene]]
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* [[Tetrahydrocannabihexol]]
* [[Tetrahydrocannabihexol]]
* [[THCP-O-acetate]]
* [[THCP-O-acetate]]
* [[O-1871]]
* [[DMHP]]
* [[Cannabicyclohexanol]]


== References ==
== References ==
{{reflist}}
{{reflist|30em}}


{{Cannabinoids}}
{{Cannabinoids}}
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[[Category:Phytocannabinoids]]
[[Category:Phytocannabinoids]]
[[Category:Benzochromenes]]
[[Category:Benzochromenes]]


{{Cannabinoid-stub}}

Revision as of 04:01, 1 June 2024

Not to be confused with Tetrakis(hydroxymethyl)phosphonium chloride (THPC).
See also: Cannabidiphorol (CBDP)
Tetrahydrocannabiphorol
Clinical data
Other names(-)-Trans-Δ9-tetrahydrocannabiphorol
Δ9-THCP
(C7)-Δ9-THC
THC-Heptyl
Identifiers
  • (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H34O2
Molar mass342.523 g·mol−1
3D model (JSmol)
  • CCCCCCCc3cc2OC(C)(C)[C@@H]1CCC(C)=C[C@H]1c2c(O)c3
  • InChI=1S/C23H34O2/c1-5-6-7-8-9-10-17-14-20(24)22-18-13-16(2)11-12-19(18)23(3,4)25-21(22)15-17/h13-15,18-19,24H,5-12H2,1-4H3/t18-,19-/m1/s1
  • Key:OJTMRZHYTZMJKX-RTBURBONSA-N

Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 agonist which was known as a synthetic homologue of THC,[1] but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.[2][3] It is structurally similar to Δ9-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than Δ9-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB1, approximately 33 times that of Δ9-THC (40 nM at CB1).[4]

THCP was studied by Roger Adams as early as 1942.[5]

Isomers

Delta-3-THCP

Δ3-THCP [1]

The Δ3/Δ6a(10a) isomer Δ3-THCP was synthesised in 1941, and was found to have around the same potency as Δ3-THC, unlike the hexyl homologue parahexyl which was significantly stronger.[6]

Delta-8-THCP

JWH-091 (Δ8-THCP) [2], CAS# 51768-60-6

The Δ8 isomer is also known as a synthetic cannabinoid under the code name JWH-091.[7][8] It's unconfirmed whether or not Δ8-THCP is found naturally in cannabis plants, but likely is due to Δ8-THC itself being a degraded form of Δ9-THC.[9] JWH-091 has approximately double the binding affinity at the CB1 receptor (22 nM ± 3.9 nM) in comparison to Δ9-THC (40.7 nM ± 1.7 nM) or Δ8-THC (44 nM ± 12 nM),[8] but appears significantly lower in vitro than the binding activity of Δ9-THCP (Ki = 1.2 nM)[4]

Natural occurrence in cannabis

The Δ9 isomer of THCP occurs naturally in cannabis, but in small amounts. A 2021 study reported the content of Δ9-THCP ranging from 0.0023% to 0.0136% (w/w) (approximately 0.02–0.13 mg/g) without correlation to THC percentage in Δ9-THC-dominant strains of cannabis; that study failed to detect THCP in CBD-dominant strains.[2][10]

See also

References

  1. ^ Harvey DJ (March 1985). "Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 15 (3): 187–197. doi:10.3109/00498258509045349. PMID 2992174.
  2. ^ a b Bueno J, Greenbaum EA (February 2021). "(-)-trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes". Journal of Natural Products. 84 (2): 531–536. doi:10.1021/acs.jnatprod.0c01034. PMID 33565878. S2CID 231866062.
  3. ^ Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, et al. (December 2021). "The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions". Talanta. 235: 122704. doi:10.1016/j.talanta.2021.122704. hdl:11380/1250339. PMID 34517579.
  4. ^ a b Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, et al. (December 2019). "A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol". Scientific Reports. 9 (1): 20335. Bibcode:2019NatSR...920335C. doi:10.1038/s41598-019-56785-1. PMC 6937300. PMID 31889124.
  5. ^ 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.
  6. ^ Adams R, Loewe S, Jelinek C, Wolff H (July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX". Journal of the American Chemical Society. 63 (7): 1971–1973. doi:10.1021/ja01852a052.
  7. ^ Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, et al. (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics. 290 (3): 1065–1079. PMID 10454479.
  8. ^ a b 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.
  9. ^ Hazekamp A, Fischedick JT, Díez ML, Lubbe A, Ruhaak RL (2010). "Chemistry of Cannabis". Comprehensive Natural Products II. pp. 1033–1084. doi:10.1016/B978-008045382-8.00091-5. ISBN 978-0-08-045382-8.
  10. ^ Bueno J, Greenbaum EA (2021). "(-)- trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes". Journal of Natural Products. 84 (2): 531–536. doi:10.1021/acs.jnatprod.0c01034. PMID 33565878. S2CID 231866062. Retrieved 19 Feb 2024.
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