Jump to content

Dexanabinol: Difference between revisions

Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
CheMoBot (talk | contribs)
Bots
141,565 edits
Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia talk:
Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5
 
(51 intermediate revisions by 35 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| verifiedrevid = 443586184
| Watchedfields = changed
⚫
| IUPAC_name = (6aS,10aS)-9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol
⚫
| verifiedrevid =
| image = HU-211_structure.png
⚫
| IUPAC_name = (,)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
| image = Dexanabinol Structure.svg
| width = 200
| width = 200


Line 8: Line 11:
| tradename =
| tradename =
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 112924-45-5
| CAS_number = 112924-45-5
| ATC_prefix = none
| ATC_prefix = none
Line 22: Line 26:
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R6VT8U5372
| UNII = R6VT8U5372
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 96934
| ChEMBL = 334533
| DrugBank = DB06444
| smiles = Oc2cc(cc1OC([C@H]3C/C=C(\C[C@@H]3c12)CO)(C)C)C(C)(C)CCCCCC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C25H38O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h10,14-15,19-20,26-27H,6-9,11-13,16H2,1-5H3/t19-,20-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SSQJFGMEZBFMNV-PMACEKPBSA-N


<!--Chemical data-->
<!--Chemical data-->
| C=25 | H=38 | O=3
| C=25 | H=38 | O=3
| molecular_weight = 386.567 g/mol
}}
}}


'''Dexanabinol''' ('''HU-211''') is a [[synthetic cannabinoid]] derivative, which is the "unnatural" [[enantiomer]] of the potent cannabinoid agonist [[HU-210]].<ref name="pmid10903397">{{cite journal |author=Pop E |title=Nonpsychotropic synthetic cannabinoids |journal=Current Pharmaceutical Design |volume=6 |issue=13 |pages=1347–60 |year=2000 |month=September |pmid=10903397 |doi= 10.2174/1381612003399446|url=}}</ref> Unlike other [[cannabinoid]] derivatives, HU-211 does not act as a [[cannabinoid receptor]] agonist, but instead has [[NMDA antagonist]] effects.<ref name="pmid2556719">{{cite journal |title=Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=86 |issue=23 |pages=9584–7 |year=1989 |month=December |pmid=2556719 |pmc=298542 |doi= 10.1073/pnas.86.23.9584|url= |author1=Feigenbaum JJ |author2=Bergmann F |author3=Richmond SA |author4=Mechoulam R |author5=Nadler V |author6=Kloog Y |author7=Sokolovsky M |author-separator=, |author-name-separator=}}</ref> It therefore does not produce cannabis-like effects, but is [[anticonvulsant]] and [[neuroprotective]], and is widely used in scientific research as well as currently being studied for practical applications such as treatment of [[head injury]] or [[stroke]].<ref name="pmid7477742">{{cite journal |title=Development of HU-211 as a neuroprotectant for ischemic brain damage |journal=Neurological Research |volume=17 |issue=4 |pages=275–80 |year=1995 |month=August |pmid=7477742 |doi= |url= |author1=Biegon A |author2=Joseph AB |author-separator=, |author-name-separator=}}</ref><ref name="pmid14534855">{{cite journal |author=Darlington CL |title=Dexanabinol: a novel cannabinoid with neuroprotective properties |journal=IDrugs : the Investigational Drugs Journal |volume=6 |issue=10 |pages=976–9 |year=2003 |month=October |pmid=14534855 |doi= |url=}}</ref><ref name="pmid19110197">{{cite journal |title=Multifunctional drugs for head injury |journal=Neurotherapeutics : the Journal of the American Society for Experimental NeuroTherapeutics |volume=6 |issue=1 |pages=28–42 |year=2009 |month=January |pmid=19110197 |doi=10.1016/j.nurt.2008.10.036 |url= |author1=Vink R |author2=Nimmo AJ |author-separator=, |author-name-separator=}}</ref> It was shown to be safe in [[clinical trials]].<ref name="pmid16361021">{{cite journal |author=Maas AI, Murray G, Henney H, ''et al.'' |title=Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomised, placebo-controlled, clinical trial |journal=Lancet Neurol |volume=5 |issue=1 |pages=38–45 |year=2006 |month=January |pmid=16361021 |doi=10.1016/S1474-4422(05)70253-2 |url=}}</ref>
'''Dexanabinol''' ('''HU-211''') is a [[synthetic cannabinoid]] derivative is the "unnatural" [[enantiomer]] of the potent cannabinoid agonist [[HU-210]].<ref name="pmid10903397">{{cite journal |=Pop E |title=Nonpsychotropic synthetic cannabinoids |journal=Current Pharmaceutical Design |volume=6 |issue=13 |pages=1347–60 | =September |pmid=10903397 |doi= 10.2174/1381612003399446}}</ref> Unlike other [[cannabinoid]] derivatives, HU-211 does not act as a [[cannabinoid receptor]] agonist, but instead [[NMDA antagonist]].<ref name="pmid2556719">{{cite journal |title=Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=86 |issue=23 |pages=9584–7 |=1989 | pmid=2556719 |pmc=298542 |doi= 10.1073/pnas.86.23.9584 | = | = }}</ref> It therefore does not produce cannabis-like effects, but is [[anticonvulsant]] and [[neuroprotective]], and is widely used in scientific research as well as currently being studied for applications such as head injury or .<ref name="pmid7477742">{{cite journal |title=Development of HU-211 as a neuroprotectant for ischemic brain damage |journal=Neurological Research |volume=17 |issue=4 |pages=275–80 | =August | = | = }}</ref><ref name="pmid14534855">{{cite journal |=Darlington CL |title=Dexanabinol: a novel cannabinoid with neuroprotective properties |journal=IDrugs |volume=6 |issue=10 |pages=976–9 |=2003 | pmid = }}</ref><ref name="pmid19110197">{{cite journal |= | |volume=6 |issue=1 |pages=28–42 |=2009 | pmid=19110197 |doi=10.1016/j.nurt.2008.10.036 }}</ref> It was shown to be safe in [[clinical trials]]<ref name="pmid16361021">{{cite journal |=Maas AI, Murray G, Henney H, |title=Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomised, placebo-controlled, clinical trial |journal=Lancet |volume=5 |issue=1 |pages=38–45 | =January |pmid=16361021 |doi=10.1016/S1474-4422(05)70253-2 |url=}}</ref>


== Clinical trials ==
⚫
==References==
Dexanabinol has been studied in IV administration and oral dosing.<ref>{{Cite news|url = http://etherapeutics.co.uk/userfiles/file/ETS2101_Phase_Ia_to_Phase_Ib_Final.pdf|title = e-Therapeutics Reports Progress in ETS2101 Phase 1a and Oral Dosing Studies|date = 18 December 2014|archive-url = https://web.archive.org/web/20150205225759/http://etherapeutics.co.uk/userfiles/file/ETS2101_Phase_Ia_to_Phase_Ib_Final.pdf|archive-date = 5 February 2015|url-status = dead}}</ref> e-Therapeutics is evaluating the compound in clinical trials for brain and solid cancers.<ref>{{Cite web|url = http://etherapeutics.co.uk/pipeline.html|title = Clinical Development Pipeline|access-date = Feb 5, 2015|archive-url = https://web.archive.org/web/20150205231338/http://etherapeutics.co.uk/pipeline.html|archive-date = February 5, 2015|url-status = dead}}</ref> Phase II studies are planned based on the results of the current trials.

A phase 1b study for hepatocellular carcinoma and pancreatic cancer was started in 2015.<ref>{{Cite web|title = A Study of Dexanabinol in Combination With Chemotherapy in Patients With Advanced Tumours - Full Text View - ClinicalTrials.gov|url = https://clinicaltrials.gov/ct2/show/NCT02423239?term=Dexanabinol&rank=1|website = clinicaltrials.gov|access-date = 2015-09-18}}</ref>

==Legal status==
HU-211 is not listed in the schedules set out by the [[United Nations]]' [[Single Convention on Narcotic Drugs]] from 1961 nor their [[Convention on Psychotropic Substances]] from 1971,<ref name="UNCPS">{{Cite web |url=https://www.unodc.org/unodc/en/commissions/CND/conventions.html |title=UN International Drug Control Conventions |access-date=2016-08-07 |archive-date=2014-03-17 |archive-url=https://web.archive.org/web/20140317082038/http://www.unodc.org/unodc/en/commissions/CND/conventions.html |url-status=dead }}</ref> so the signatory countries to these international drug control treaties are not required by said treaties to control HU-211.

===United States===
HU-211 is not listed in the [[List of Schedule I drugs (US)|list of scheduled controlled substances]] in the USA.<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=§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 therefore not [[Controlled Substances Act#Schedules of controlled substances|scheduled]] at the [[Federal government of the United States|federal level]] in the [[United States]], but it is possible that HU-211 could legally be considered an [[Structural analog#Chemistry|analog]] of Delta-8-THC (one of the THC isomers which is in Schedule I under the designation of "Tetrahydrocannabinols"), and therefore sales or [[Drug possession|possession]] could potentially be prosecuted under the [[Federal Analogue Act]].<ref>[https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary]</ref>

HU-211 is a Schedule I controlled substance in [[Alabama]].<ref>{{cite web | url=https://legiscan.com/AL/text/SB333/2014 | title=Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd. | date=March 2014 | access-date=2 February 2017}}</ref>

HU-211 is a Schedule I [[controlled substance]] in the state of [[Florida]] making it illegal to buy, sell, or possess in Florida.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">[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>

Effective January 1, 2016, HU-211 is a regulated drug in Vermont designated as a "Hallucinogenic Drug."<ref>[http://www.healthvermont.gov/sites/default/files/documents/2017/01/REG_regulated-drugs.pdf Vermont DOH - Regulated Drug Rule 2016 .PDF]</ref>

== See also ==
*[[Etonitazene]]
*[[Norbinaltorphimine]]

⚫
==References==
{{Reflist}}
{{Reflist}}


{{Glutamate receptor ligands}}
{{Cannabinoids}}
{{Cannabinoids}}
{{Ionotropic glutamate receptor modulators}}


[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:NMDA receptor antagonists]]
[[Category:Phenols]]
[[Category:Phenols]]
[[Category:Benzochromenes]]
[[Category:Benzochromenes]]
[[Category:Alcohols]]
[[Category:]]
[[Category:HU cannabinoids]]
[[Category:HU cannabinoids]]

{{pharma-stub}}
{{cannabinoid-stub}}

[[de:Dexanabinol]]
Retrieved from "https://en.wikipedia.org/wiki/Special:ComparePages"