Hexahydrocannabinol: Difference between revisions

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| width2 = 220
| width2 = 220
| licence_US =
| licence_US =
| legal_UK = PSA [[Unenforced]]{{citation needed|reason=No confirmation of HHC being categorised as Class B in the UK to be found (unlike hexahydrocannabinol-O-acetate or HHC-O); article's text suggests that it WOULD be considered illegal in UK, not that it actually is illegal|date=February 2024}}
| legal_UK = Class B{{citation needed|reason=No confirmation of HHC being categorised as Class B in the UK to be found (unlike hexahydrocannabinol-O-acetate or HHC-O); article's text suggests that it WOULD be considered illegal in UK, not that it actually is illegal|date=February 2024}}
| legal_US = Unscheduled, in general legal for recreationasl use in most countries.
| legal_US = ?
| CAS_number = 6692-85-9
| CAS_number = 6692-85-9
| CAS_supplemental = (racemic)<BR>946512-74-9 (6aR,10aR)
| CAS_supplemental = (racemic)<BR>946512-74-9 (6aR,10aR)
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Hexahydrocannabinol should not be confused with the related compounds [[9-Nor-9β-hydroxyhexahydrocannabinol]] (9-Nor-9Beta-HHC) or [[9-Hydroxyhexahydrocannabinol]] (9-OH-HHC) or [[11-Hydroxyhexahydrocannabinol]] (11-OH-HHC and 7-OH-HHC), all of which have also sometimes been referred to as "HHC".{{citation needed|date=December 2021}}
Hexahydrocannabinol should not be confused with the related compounds [[9-Nor-9β-hydroxyhexahydrocannabinol]] (9-Nor-9Beta-HHC) or [[9-Hydroxyhexahydrocannabinol]] (9-OH-HHC) or [[11-Hydroxyhexahydrocannabinol]] (11-OH-HHC and 7-OH-HHC), all of which have also sometimes been referred to as "HHC".{{citation needed|date=December 2021}}


¬== Legality ==
== Legality ==
Hexahidrocannabinol also known as HHC, is not controlled, audited, prohibited, outlawed, restricted, banned, regulated or forbidden is the most countries, because doesnt is named nor neither added nor controlled under the single convention on narcotic drugs or the convention on psychotropic substances, as doesnt is a substance subject to international auditing, meanwhile and therefore is legal and can be openly and freely sold always and when doesnt be sold for human consumption, is legal and could be sold for medical and research purposes in most countries in the world but if is sold for human consumption could be persecuted, punishable and controlled under several analogue acts in several countries or under the attempt of sell or consume, however the drug is a legal gray are and the legal status in the most countries is unknown and ambiguous.
The [[Agence nationale de sécurité du médicament et des produits de santé|ANSM]] announced the ban (production, sale and use) of HHC and two of its derivatives, [[HHC-acetate]] (HHCO) and [[hexahydrocannabiphorol]] (HHCP), on [[France|French]] territory from June 13, 2023.<ref>{{Cite news |date=2023-06-12 |title=Cannabis : le HHC sera interdit en France à partir de mardi |language=fr |work=Le Monde.fr |url=https://www.lemonde.fr/sante/article/2023/06/12/cannabis-le-hhc-sera-interdit-en-france-a-partir-de-mardi_6177293_1651302.html |access-date=2023-06-12}}</ref><ref name=":1">{{Cite web |title=Actualité - L'ANSM classe l'hexahydrocannabinol (HHC) et deux de ses dérivés sur la liste des stupéfiants |url=https://ansm.sante.fr/actualites/lansm-classe-lhexahydrocannabinol-hhc-et-deux-de-ses-derives-sur-la-liste-des-stupefiants |access-date=2023-06-12 |website=ANSM |language=fr}}</ref>
The [[Agence nationale de sécurité du médicament et des produits de santé|ANSM]] announced the ban (production, sale and use) of HHC and two of its derivatives, [[HHC-acetate]] (HHCO) and [[hexahydrocannabiphorol]] (HHCP), on [[France|French]] territory from June 13, 2023.<ref>{{Cite news |date=2023-06-12 |title=Cannabis : le HHC sera interdit en France à partir de mardi |language=fr |work=Le Monde.fr |url=https://www.lemonde.fr/sante/article/2023/06/12/cannabis-le-hhc-sera-interdit-en-france-a-partir-de-mardi_6177293_1651302.html |access-date=2023-06-12}}</ref><ref name=":1">{{Cite web |title=Actualité - L'ANSM classe l'hexahydrocannabinol (HHC) et deux de ses dérivés sur la liste des stupéfiants |url=https://ansm.sante.fr/actualites/lansm-classe-lhexahydrocannabinol-hhc-et-deux-de-ses-derives-sur-la-liste-des-stupefiants |access-date=2023-06-12 |website=ANSM |language=fr}}</ref>


In the [[United Kingdom]], HHC could be likely be considered illegal in the theory but not in the practice under the [[Psychoactive Substances Act 2016]], however the most possible is that the drug is not controlled and is not enforced in the UK and as such could be considered and classified as legal, alloweb and permitted and as such could be sold and traded openly in shops without arousing suspicion by the hand of authorities and can be sold legally without being controlled, seized or regulated by the authorities.
In the [[United Kingdom]], HHC would likely be considered illegal under the [[Psychoactive Substances Act 2016]].


Several European countries ([[Denmark]], [[Belgium]]) also recently{{when|date=June 2023}} banned the sale of HHC.<ref name=":1" />{{verification needed|reason=Although this is a reliable site (France's [[Agence nationale de sécurité du médicament et des produits de santé]]), cited article on it merely mentions that "in Europe, other countries have recently banned the sale of HHC such as Austria, Belgium, Denmark and UK" - whilst confirmation for Austria could be easily obtained, there's nothing that could be found easily to confirm the banning of HHC in Denmark or Belgium, and in Britain legally HHC remains in a grey area up to date and to this day and as such is a legal and an unscheduled drug in the uk,.|date=February 2024}}
Several European countries ([[Denmark]], [[Belgium]]) also recently{{when|date=June 2023}} banned the sale of HHC.<ref name=":1" />{{verification needed|reason=Although this is a reliable site (France's [[Agence nationale de sécurité du médicament et des produits de santé]]), cited article on it merely mentions that "in Europe, other countries have recently banned the sale of HHC such as Austria, Belgium, Denmark and UK" - whilst confirmation for Austria could be easily obtained, there's nothing that could be found easily to confirm the banning of HHC in Denmark or Belgium (and in Britain legally HHC remains in grey area to this day, so THAT STATEMENT IS NOT ENTIRELY CORRECT).|date=February 2024}}


[[File:Legality HHC EU (corrected legend) Map.png|thumb|474x474px|Legality of HHC in [[European Union|EU]] as of November 2023.]]
[[File:Legality HHC EU (corrected legend) Map.png|thumb|474x474px|Legality of HHC in [[European Union|EU]] as of November 2023.]]
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HHC has been banned in Slovenia since November 15th, 2023.<ref>{{Cite web |title=eUprava - Predlog predpisa |url=https://e-uprava.gov.si/si/drzava-in-druzba/e-demokracija/predlogi-predpisov/predlog-predpisa.html?id=15805 |access-date=2023-12-24 |website=e-uprava.gov.si}}</ref>
HHC has been banned in Slovenia since November 15th, 2023.<ref>{{Cite web |title=eUprava - Predlog predpisa |url=https://e-uprava.gov.si/si/drzava-in-druzba/e-demokracija/predlogi-predpisov/predlog-predpisa.html?id=15805 |access-date=2023-12-24 |website=e-uprava.gov.si}}</ref>


The German expert committee for narcotics suggested that HHC be added to the annex of {{ill|Novel Psychoactive Substances Act (NpSG)|de|Neue-psychoaktive-Stoffe-Gesetz}} in a meeting on December 4, 2023.<ref>{{Cite web |title=Sachverständigenausschuss für Betäubungsmittel nach § 1 Abs. 2 BtMG und Neue-psychoaktive-Stoffe nach § 7 NpSG |url=https://www.bfarm.de/DE/Bundesopiumstelle/Betaeubungsmittel/Sachverstaendigenausschuss/Sitzungen/Ergebnisse_59.html?nn=595366 |access-date=2024-01-15 |website=www.bfarm.de |language=de}}</ref> This recommendation has to date not been enacted by the [[Cabinet of Germany|German government]], although this is little likely to occur in February of 2024, the drug is fully legal in germany without exceptions and is openly sold in smartshops, in headshops and in grocery stores around the country.
The German expert committee for narcotics suggested that HHC be added to the annex of {{ill|Novel Psychoactive Substances Act (NpSG)|de|Neue-psychoaktive-Stoffe-Gesetz}} in a meeting on December 4, 2023.<ref>{{Cite web |title=Sachverständigenausschuss für Betäubungsmittel nach § 1 Abs. 2 BtMG und Neue-psychoaktive-Stoffe nach § 7 NpSG |url=https://www.bfarm.de/DE/Bundesopiumstelle/Betaeubungsmittel/Sachverstaendigenausschuss/Sitzungen/Ergebnisse_59.html?nn=595366 |access-date=2024-01-15 |website=www.bfarm.de |language=de}}</ref> This recommendation has to date not been enacted by the [[Cabinet of Germany|German government]], although this is likely to occur in February of 2024.


== See also ==
== See also ==

Revision as of 23:11, 9 February 2024

Hexahydrocannabinol
Legal status
Legal status
Identifiers
  • (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H32O2
Molar mass316.485 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2[C@@H]3CC(CC[C@H]3C(OC2=C1)(C)C)C)O
  • InChI=1S/C21H32O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h12-14,16-17,22H,5-11H2,1-4H3/t14?,16-,17-/m1/s1
  • Key:XKRHRBJLCLXSGE-VNCLPFQGSA-N

Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol (THC). It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in Cannabis sativa,[1][2] but can also be produced synthetically by hydrogenation of cannabis extracts.[3] The synthesis and bioactivity of HHC was first reported in 1940 by Roger Adams using tetrahydrocannabinol prepared from cannabidiol.[4]

HHC is a psychoactive substance with effects reportedly similar to that of THC.[5] HHC vaporizers have been openly sold at head shops and convenience stores since at least the early 2020s in North America and Europe. [6][7]

Chemistry

Several research groups have successfully synthesized (+)-HHC and (-)-HHC using citronellal and olivetol,[8] as well as other related compounds.[9] HHC and related hydrogenated cannabinoid epimers were elucidated using various NMR spectroscopic techniques (ie, NOSY, COSY, 1H) and the diastereomers were isolated using LC-MS and SCFC.[10] While similar compounds have previously been identified in cannabis,[11] hexahydrocannabinol itself has rarely been isolated from the plant. The de Las Heras group in 2020 took lipid extract from Cannabis sativa seeds and discovered 43 cannabinoids in the crude extract; one of them being hexahydrocannabinol. It has two diastereomers at the methyl (9) position. HHC is typically made from CBD. There are no double bonds in the cyclohexyl ring like D8/D9 have—they have been removed from the structure and hydrogens have been added to the compound.[12][13] Similar structural analogs of HHC have been demonstrated to bind to the CB1 receptor and produce cannabinoid effects in animals, with the 9β-HHC enantiomer being much more active than 9α-HHC.[14] While HHC has been shown to bind to the CB1 receptor, it binds with weaker affinity than THC, which has typically been an indication that it is not as intoxicating as typical THC.

Several structurally related HHC analogs have been found to be naturally occurring in Cannabis including cannabiripsol,[15] 9α-hydroxyhexahydrocannabinol, 7-oxo-9α-hydroxyhexa-hydrocannabinol, 10α-hydroxyhexahydrocannabinol, 10aR-hydroxyhexahydrocannabinol and 1′S-hydroxycannabinol,[11] 10α-hydroxy-Δ(9,11)-hexahydrocannabinol and 9β,10β-epoxyhexahydrocannabinol.[16][17]

HHC itself has been found as a degradation byproduct of THC in a similar way that Cannabinol and Delta-8-THC can be formed by the Cannabis plant from Delta-9-THC degradation. The degradation of D9-THC that forms HHC is the reduction of the double carbon bonds that would typically make up the delta isomer position on THCs structure.[18][19]

Delta-9-THC was discovered to partly metabolize into 11-Hydroxy-THC and alpha,10 alpha-epoxy-hexahydrocannabinol along with 1,2-epoxy-hexahydrocannabinol.[20] Cannabidiol was discovered to partly metabolize into 9α-hydroxy-HHC and 8-hydroxy-iso-HHC inside the body. In the presence of alcohol, the methoxy or ethoxy analogs such as 9-methoxy-HHC, 10-methoxy-HHC, 9-ethoxy-HHC and 10-ethoxy-HHC can be formed.[21]

Hexahydrocannabinol should not be confused with the related compounds 9-Nor-9β-hydroxyhexahydrocannabinol (9-Nor-9Beta-HHC) or 9-Hydroxyhexahydrocannabinol (9-OH-HHC) or 11-Hydroxyhexahydrocannabinol (11-OH-HHC and 7-OH-HHC), all of which have also sometimes been referred to as "HHC".[citation needed]

Legality

The ANSM announced the ban (production, sale and use) of HHC and two of its derivatives, HHC-acetate (HHCO) and hexahydrocannabiphorol (HHCP), on French territory from June 13, 2023.[22][23]

In the United Kingdom, HHC would likely be considered illegal under the Psychoactive Substances Act 2016.

Several European countries (Denmark, Belgium) also recently[when?] banned the sale of HHC.[23][verification needed]

Legality of HHC in EU as of November 2023.

In Austria, HHC has been banned since 23 March 2023 due to the amendment of the New Psychoactive Substances Ordinance (known in German as Neue-Psychoaktive-Substanzen-Verordnung or NPSV).[24]

HHC has been banned in Sweden since July 11, 2023, and in Italy since July 28, 2023.[25]

HHC has been banned in Lithuania since November 23, 2022.

HHC has been banned in Slovenia since November 15th, 2023.[26]

The German expert committee for narcotics suggested that HHC be added to the annex of Novel Psychoactive Substances Act (NpSG) [de] in a meeting on December 4, 2023.[27] This recommendation has to date not been enacted by the German government, although this is likely to occur in February of 2024.

See also

References

  1. ^ 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. S2CID 34267092.
  2. ^ Basas-Jaumandreu J, de Las Heras FX (March 2020). "GC-MS Metabolite Profile and Identification of Unusual Homologous Cannabinoids in High Potency Cannabis sativa". Planta Medica. 86 (5): 338–347. doi:10.1055/a-1110-1045. hdl:2117/188476. PMID 32053835. S2CID 211113472.
  3. ^ US 9694040, Scialdone MA, "Hydrogenation of cannabis oil", issued 10 November 2016, assigned to Research Grow Labs. 
  4. ^ Adams R, Pease DC, Clark JH (September 1940). "Structure of Cannabidiol. VI. Isomerization of Cannabidiol to Tetrahydrocannabinol, a Physiologically Active Product. Conversion of Cannabidiol to Cannabinol". Journal of the American Chemical Society. 62 (9): 2402–2405. doi:10.1021/ja01866a040.
  5. ^ Docampo-Palacios M, Ramirez G, Tesfatsion T, Okhovat A, Pittiglio M, Ray K, Cruces W (3 August 2023). "Saturated Cannabinoids: Update on synthesis strategies and biological studies of these emerging cannabinoid analogs". ChemRxiv. doi:10.26434/chemrxiv-2023-3hk1c.
  6. ^ European Monitoring Centre for Drugs and Drug Addiction. (2023). Technical Report: Hexahydrocannabinol (HHC) and related substances. European Monitoring Centre for Drugs and Drug Addiction. doi:10.2810/852912.
  7. ^ Ujváry I (2023). "Hexahydrocannabinol and closely related semi-synthetic cannabinoids: A comprehensive review". Drug Testing and Analysis. doi:10.1002/dta.3519. PMID 37269160. S2CID 259046522.
  8. ^ Lee YR, Xia L (2008). "Efficient one-pot synthetic approaches for cannabinoid analogues and their application to biologically interesting (-)-hexahydrocannabinol and (+)-hexahydrocannabinol". Tetrahedron Letters. 49: 3283. doi:10.1016/j.tetlet.2008.03.075.
  9. ^ Maurya V, Appayee C (January 2020). "Enantioselective Total Synthesis of Potent 9β-11-Hydroxyhexahydrocannabinol". The Journal of Organic Chemistry. 85 (2): 1291–1297. doi:10.1021/acs.joc.9b02962. PMID 31833372. S2CID 209343301.
  10. ^ Collins A, Ramirez G, Tesfatsion T, Ray KP, Caudill S, Cruces W (2023). "Synthesis and Characterization of the Diastereomers of HHC and H4CBD". Natural Product Communications. 18 (3): 1934578X2311589. doi:10.1177/1934578X231158910. ISSN 1934-578X.
  11. ^ a b Ahmed SA, Ross SA, Slade D, Radwan MM, Khan IA, ElSohly MA (September 2015). "Minor oxygenated cannabinoids from high potency Cannabis sativa L". Phytochemistry. 117: 194–199. Bibcode:2015PChem.117..194A. doi:10.1016/j.phytochem.2015.04.007. PMC 4883105. PMID 26093324.
  12. ^ Harvey DJ, Brown NK (May 1991). "In vitro metabolism of the equatorial C11-methyl isomer of hexahydrocannabinol in several mammalian species". Drug Metabolism and Disposition. 19 (3): 714–716. PMID 1680642.
  13. ^ Harvey DJ, Brown NK (November 1991). "Comparative in vitro metabolism of the cannabinoids". Pharmacology, Biochemistry, and Behavior. 40 (3): 533–540. doi:10.1016/0091-3057(91)90359-a. PMID 1806943. S2CID 25827210.
  14. ^ Reggio PH, Greer KV, Cox SM (July 1989). "The importance of the orientation of the C9 substituent to cannabinoid activity". Journal of Medicinal Chemistry. 32 (7): 1630–1635. doi:10.1021/jm00127a038. PMID 2738895.
  15. ^ Boeren EG, Elsohly MA, Turner CE (October 1979). "Cannabiripsol: a novel Cannabis constituent". Experientia. 35 (10): 1278–1279. doi:10.1007/BF01963954. PMID 499397. S2CID 19529732.
  16. ^ Radwan MM, ElSohly MA, El-Alfy AT, Ahmed SA, Slade D, Husni AS, et al. (June 2015). "Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa". Journal of Natural Products. 78 (6): 1271–1276. doi:10.1021/acs.jnatprod.5b00065. PMC 4880513. PMID 26000707.
  17. ^ Peter, Alexendra. "HHC (Hexahydrocannabinol)". Happy420. Retrieved 22 June 2023.
  18. ^ Turner CE, Hadley KW, Fetterman PS, Doorenbos NJ, Quimby MW, Waller C (October 1973). "Constituents of Cannabis sativa L. IV. Stability of cannabinoids in stored plant material". Journal of Pharmaceutical Sciences. 62 (10): 1601–1605. doi:10.1002/jps.2600621005. PMID 4752104.
  19. ^ Garrett ER, Gouyette AJ, Roseboom H (January 1978). "Stability of tetrahydrocannabinols II". Journal of Pharmaceutical Sciences. 67 (1): 27–32. doi:10.1002/jps.2600670108. PMID 22740.
  20. ^ Narimatsu S, Watanabe K, Matsunaga T, Yamamoto I, Imaoka S, Funae Y, Yoshimura H (January 1992). "Cytochrome P-450 isozymes involved in the oxidative metabolism of delta 9-tetrahydrocannabinol by liver microsomes of adult female rats". Drug Metabolism and Disposition. 20 (1): 79–83. PMID 1347001.
  21. ^ Golombek P, Müller M, Barthlott I, Sproll C, Lachenmeier DW (June 2020). "Conversion of Cannabidiol (CBD) into Psychotropic Cannabinoids Including Tetrahydrocannabinol (THC): A Controversy in the Scientific Literature". Toxics. 8 (2): 41. doi:10.3390/toxics8020041. PMC 7357058. PMID 32503116.
  22. ^ "Cannabis : le HHC sera interdit en France à partir de mardi". Le Monde.fr (in French). 2023-06-12. Retrieved 2023-06-12.
  23. ^ a b "Actualité - L'ANSM classe l'hexahydrocannabinol (HHC) et deux de ses dérivés sur la liste des stupéfiants". ANSM (in French). Retrieved 2023-06-12.
  24. ^ "Office for Tobacco Coordination - News and Product Warnings - AGES - Hexahydrocannabinol (HHC), new regulation in the NPSV". Österreichische Agentur für Gesundheit und Ernährungssicherheit. Retrieved 7 February 2024.
  25. ^ "Gazzetta Ufficiale". www.gazzettaufficiale.it. Retrieved 2023-08-06.
  26. ^ "eUprava - Predlog predpisa". e-uprava.gov.si. Retrieved 2023-12-24.
  27. ^ "Sachverständigenausschuss für Betäubungsmittel nach § 1 Abs. 2 BtMG und Neue-psychoaktive-Stoffe nach § 7 NpSG". www.bfarm.de (in German). Retrieved 2024-01-15.
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