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'''HU-308''' (also known as '''onternabez''', '''HU308''', '''PPP-003''' and '''ARDS-003''') is a [[cannabidiol]] (CBD)-derivative drug {{Citation needed|date=January 2022}} that acts as a potent [[cannabinoid]] [[agonist]]. It is highly selective for the [[cannabinoid receptor type 2|cannabinoid-2 receptor]] (CB<sub>2</sub> receptor) subtype, with a selectivity more than 5,000 times greater for the CB<sub>2</sub> receptor than the [[CB1 receptor|CB<sub>1</sub> receptor]].<ref name="Mechoulam 1990">{{cite journal| vauthors = Mechoulam R, Lander N, Breuer A, Zahalka J |date=1990-04-11|title=Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative|journal=Tetrahedron Asymmetry|volume=1|issue=5|language=en|pages=315–318|doi=10.1016/S0957-4166(00)86322-3|pmid=|pmc=|issn=|doi-access=free}}</ref><ref name="Hanus et al 1999">{{cite journal | vauthors = Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, Pertwee RG, Ross RA, Mechoulam R, Fride E | display-authors = | title = HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 96 | issue = 25 | pages = 14228–33 | date = December 1999 | pmid = 10588688 | pmc = 24419 | doi = 10.1073/pnas.96.25.14228 | bibcode = 1999PNAS...9614228H | doi-access = free}}
'''HU-308''' (also known as '''onternabez''', '''HU308''', '''PPP-003''' and '''ARDS-003''') is a [[cannabidiol]] (CBD)-derivative drug {{Citation needed|date=January 2022}} that acts as a potent [[cannabinoid]] [[agonist]]. It is highly selective for the [[cannabinoid receptor type 2|cannabinoid-2 receptor]] (CB<sub>2</sub> receptor) subtype, with a selectivity more than 5,000 times greater for the CB<sub>2</sub> receptor than the [[CB1 receptor|CB<sub>1</sub> receptor]].<ref name="Mechoulam 1990">{{cite journal| vauthors = Mechoulam R, Lander N, Breuer A, Zahalka J |date=1990-04-11|title=Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative|journal=Tetrahedron Asymmetry|volume=1|issue=5|language=en|pages=315–318|doi=10.1016/S0957-4166(00)86322-3|pmid=|pmc=|issn=|doi-access=free}}</ref><ref name="Hanus et al 1999">{{cite journal | vauthors = Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, Pertwee RG, Ross RA, Mechoulam R, Fride E | display-authors = 6 | title = HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 96 | issue = 25 | pages = 14228–14233 | date = December 1999 | pmid = 10588688 | pmc = 24419 | doi = 10.1073/pnas.96.25.14228 | doi-access = free | bibcode = 1999PNAS...9614228H }}
</ref><ref>{{cite web |title=Properties of HU-308 ~ Formula C27H42O3 |url=http://pqr.pitt.edu/mol/CFMRIVODIXTERW-BHIFYINESA-N |website=Pitt Quantum Repository |publisher=University of Pittsburgh Department of Chemistry}}</ref> The [[chemical synthesis|synthesis]] and characterization of HU-308 took place in the laboratory of [[Raphael Mechoulam]] at the [[Hebrew University of Jerusalem]] (the HU in HU-308) in the late 1990s. The [[pinene]] dimethoxy-DMH-CBD derivative HU-308 was identified as a potent peripheral CB<sub>2</sub>-selective agonist in ''in vitro'' and animal studies in 1990<ref name="Mechoulam 1990" /> and 1999.<ref name="Hanus et al 1999" />
</ref><ref>{{cite web |title=Properties of HU-308 ~ Formula C27H42O3 |url=http://pqr.pitt.edu/mol/CFMRIVODIXTERW-BHIFYINESA-N |website=Pitt Quantum Repository |publisher=University of Pittsburgh Department of Chemistry}}</ref> The [[chemical synthesis|synthesis]] and characterization of HU-308 took place in the laboratory of [[Raphael Mechoulam]] at the [[Hebrew University of Jerusalem]] (the HU in HU-308) in the late 1990s. The [[pinene]] dimethoxy-DMH-CBD derivative HU-308 was identified as a potent peripheral CB<sub>2</sub>-selective agonist in ''in vitro'' and animal studies in 1990<ref name="Mechoulam 1990" /> and 1999.<ref name="Hanus et al 1999" />


==Legal status==
==Legal status==
Tetra Bio-Pharma owns the intellectual property rights to HU-308.<ref>{{cite web |last1=Lynch |first1=Mary |last2=Kelly |first2=Melanie |title=Patent 9549906 Composition & Methods for Treatment of Ocular Inflammation &/or Pain Jan 2017 |url=https://assignment.uspto.gov/patent/index.html#/patent/search/resultAbstract?id=9549906&type=patNum |website=U.S. Patent & Trademark Office |publisher=USPTO, Panag Pharma |access-date=20 February 2021}}</ref><ref>[https://ir.tetrabiopharma.com/newsroom/press-releases/news-details/2019/Tetra-Bio-Pharma-Closesthe-Acquisition-of-Panag-Pharma/default.aspx May 2019, Tetra Bio-Pharma Closes the Acquisition of Panag Pharma]</ref>
Tetra Bio-Pharma owns the intellectual property rights to HU-308.<ref>{{cite patent | inventor = Lynch M, Kelly M | country = US | number = 9549906 | title = Composition & Methods for Treatment of Ocular Inflammation &/or Pain | gdate = 24 January 2017 | assign1 = Panag Pharma, Inc. |url= https://assignment.uspto.gov/patent/index.html#/patent/search/resultAbstract?id=9549906&type=patNum }}</ref><ref>{{cite web | url = https://ir.tetrabiopharma.com/newsroom/press-releases/news-details/2019/Tetra-Bio-Pharma-Closesthe-Acquisition-of-Panag-Pharma/default.aspx | date = May 2019 | title = Tetra Bio-Pharma Closes the Acquisition of Panag Pharma }}</ref>


HU-308 is non-psychoactive and not scheduled at the federal level in the United States.<ref>{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — Schedules of controlled substances §1308.11 Schedule I. |access-date=2014-12-17 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}</ref> It is a Schedule I [[controlled substance]] in the state of [[Florida]] making it illegal to buy, sell, or possess there.<ref>[http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html Florida Statutes - Chapter 893 - Drug abuse prevention and control]</ref>
HU-308 is non-psychoactive and not scheduled at the federal level in the United States.<ref>{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — Schedules of controlled substances §1308.11 Schedule I. |access-date=2014-12-17 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}</ref> It is a Schedule I [[controlled substance]] in the state of [[Florida]] making it illegal to buy, sell, or possess there.<ref>{{cite web | url = http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html | work = Florida Statutes | title = Chapter 893 - Drug abuse prevention and control }}</ref>


== References ==
== References ==

Revision as of 04:38, 17 May 2023

Onternabez
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
ExcretionKidneys
Identifiers
  • [(1S,2S,5S)-2-[2,6-Dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H42O3
Molar mass414.630 g·mol−1
3D model (JSmol)
  • CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC)[C@H]2C=C([C@@H]3C[C@H]2C3(C)C)CO)OC
  • InChI=1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21-,22+/m0/s1
  • Key:CFMRIVODIXTERW-FDFHNCONSA-N
 ☒NcheckY (what is this?)  (verify)

HU-308 (also known as onternabez, HU308, PPP-003 and ARDS-003) is a cannabidiol (CBD)-derivative drug [citation needed] that acts as a potent cannabinoid agonist. It is highly selective for the cannabinoid-2 receptor (CB2 receptor) subtype, with a selectivity more than 5,000 times greater for the CB2 receptor than the CB1 receptor.[1][2][3] The synthesis and characterization of HU-308 took place in the laboratory of Raphael Mechoulam at the Hebrew University of Jerusalem (the HU in HU-308) in the late 1990s. The pinene dimethoxy-DMH-CBD derivative HU-308 was identified as a potent peripheral CB2-selective agonist in in vitro and animal studies in 1990[1] and 1999.[2]

Tetra Bio-Pharma owns the intellectual property rights to HU-308.[4][5]

HU-308 is non-psychoactive and not scheduled at the federal level in the United States.[6] It is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess there.[7]

References

  1. ^ a b Mechoulam R, Lander N, Breuer A, Zahalka J (1990-04-11). "Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative". Tetrahedron Asymmetry. 1 (5): 315–318. doi:10.1016/S0957-4166(00)86322-3.
  2. ^ a b Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, et al. (December 1999). "HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor". Proceedings of the National Academy of Sciences of the United States of America. 96 (25): 14228–14233. Bibcode:1999PNAS...9614228H. doi:10.1073/pnas.96.25.14228. PMC 24419. PMID 10588688.
  3. ^ "Properties of HU-308 ~ Formula C27H42O3". Pitt Quantum Repository. University of Pittsburgh Department of Chemistry.
  4. ^ US 9549906, Lynch M, Kelly M, "Composition & Methods for Treatment of Ocular Inflammation &/or Pain", issued 24 January 2017, assigned to Panag Pharma, Inc. 
  5. ^ "Tetra Bio-Pharma Closes the Acquisition of Panag Pharma". May 2019.
  6. ^ "21 CFR — Schedules of controlled substances §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  7. ^ "Chapter 893 - Drug abuse prevention and control". Florida Statutes.

See also

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