CB-13: Difference between revisions

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Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
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{{Short description|Chemical compound}}
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{{Drugbox| verifiedrevid = 403518508
{{Drugbox
|
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| verifiedrevid = 412092673
|IUPAC_name = naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone
| IUPAC_name = Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone
| image = CB-13_structure.png
| image = CB-13_structure.png
| width= 200
| width = 120

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| CAS_number= 432047-72-8
<!--Clinical data-->
| ATC_prefix=
| tradename =
| ATC_suffix=
| legal_CA = Schedule II
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| PubChem= 9799417
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| legal_status =
| DrugBank=
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| routes_of_administration =
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| C=26 | H=24 | O=2

| molecular_weight = 368.467 g/mol
<!--Pharmacokinetic data-->
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| metabolism =
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| elimination_half-life =
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| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
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| CAS_number = 432047-72-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9XRJ6055XT
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| PubChem = 9799417
| ChemSpiderID = 7975182
| ChEMBL = 244403

<!--Chemical data-->
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| C=26 | H=24 | O=2
| smiles = c13ccccc1cccc3C(=O)c4ccc(OCCCCC)c2ccccc24
| smiles = c13ccccc1cccc3C(=O)c4ccc(OCCCCC)c2ccccc24
| StdInChI = 1S/C26H24O2/c1-2-3-8-18-28-25-17-16-24(21-13-6-7-14-22(21)25)26(27)23-15-9-11-19-10-4-5-12-20(19)23/h4-7,9-17H,2-3,8,18H2,1H3
| bioavailability=
| StdInChIKey = RSUMDJRTAFBISX-UHFFFAOYSA-N
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| metabolism =
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| elimination_half-life=
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| excretion =
| pregnancy_category =
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| legal_status =
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| routes_of_administration=
}}
}}


'''CB-13''' ('''SAB-378''')<ref>{{Cite doi|10.1124/jpet.110.169946}}</ref> is a [[cannabinoid]] drug, which acts as a potent [[agonist]] at both the [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]] receptors, but has poor [[blood-brain barrier]] penetration, and so produces only peripheral effects at low doses, with symptoms of central effects such as [[catalepsy]] only appearing at much higher dose ranges. It has [[hyperalgesia|antihyperalgesic]] properties in animal studies,<ref>Dziadulewicz EK, Bevan SJ, Brain CT, Coote PR, Culshaw AJ, Davis AJ, Edwards LJ, Fisher AJ, Fox AJ, Gentry C, Groarke A, Hart TW, Huber W, James IF, Kesingland A, La Vecchia L, Loong Y, Lyothier I, McNair K, O'Farrell C, Peacock M, Portmann R, Schopfer U, Yaqoob M, Zadrobilek J. Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration. ''Journal of Medicinal Chemistry''. 2007 Aug 9;50(16):3851-6. PMID 17630726</ref> and has progressed to preliminary human trials.<ref name="pmid19144772">{{cite journal |author=Gardin A, Kucher K, Kiese B, Appel-Dingemanse S |title=Cannabinoid receptor agonist 13, a novel cannabinoid agonist: first in human pharmacokinetics and safety |journal=Drug Metabolism and Disposition: the Biological Fate of Chemicals |volume=37 |issue=4 |pages=827–33 |year=2009 |month=April |pmid=19144772 |doi=10.1124/dmd.108.024000 |url= |issn=}}</ref>
'''CB-13''' ('''CRA13''', '''SAB-378''')<ref>{{cite journal | vauthors = Cluny NL, Keenan CM, Duncan M, Fox A, Lutz B, Sharkey KA | title = Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone (SAB378), a peripherally restricted cannabinoid CB1/CB2 receptor agonist, inhibits gastrointestinal motility but has no effect on experimental colitis in mice | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 334 | issue = 3 | pages = 973–980 | date = September 2010 | pmid = 20571060 | doi = 10.1124/jpet.110.169946 | s2cid = 9198992 }}</ref> is a [[cannabinoid]] drug, which acts as a potent [[agonist]] at both the [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]] receptors, but has poor [[blood–brain barrier]] penetration, and so produces only peripheral effects at low doses, with symptoms of central effects such as [[catalepsy]] only appearing at much higher dose ranges. It has [[hyperalgesia|antihyperalgesic]] properties in animal studies,<ref>{{cite journal | vauthors = Dziadulewicz EK, Bevan SJ, Brain CT, Coote PR, Culshaw AJ, Davis AJ, Edwards LJ, Fisher AJ, Fox AJ, Gentry C, Groarke A, Hart TW, Huber W, James IF, Kesingland A, La Vecchia L, Loong Y, Lyothier I, McNair K, O'Farrell C, Peacock M, Portmann R, Schopfer U, Yaqoob M, Zadrobilek J | display-authors = 6 | title = Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration | journal = Journal of Medicinal Chemistry | volume = 50 | issue = 16 | pages = 3851–3856 | date = August 2007 | pmid = 17630726 | doi = 10.1021/jm070317a }}</ref> and has progressed to preliminary human trials.<ref name="pmid19144772">{{cite journal | vauthors = Gardin A, Kucher K, Kiese B, Appel-Dingemanse S | title = Cannabinoid receptor agonist 13, a novel cannabinoid agonist: first in human pharmacokinetics and safety | journal = Drug Metabolism and Disposition | volume = 37 | issue = 4 | pages = 827–833 | date = April 2009 | pmid = 19144772 | doi = 10.1124/dmd.108.024000 | s2cid = 15150118 }}</ref>


==Legal Status==


As of October 2015 CB-13 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances" | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>
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==References==

<references/>
CB-13 is a Schedule I controlled substance in North Dakota.<ref>{{cite web | url = https://www.ndlegis.gov/prod/assembly/68-2023/regular/documents/23-8099-04000.pdf | title = Schedule 1 | work = Sixty-eighth Legislative Assembly of North Dakota
| date = 3 January 2023 }}</ref>

== See also ==
* [[A-PONASA]]
* [[AM-6545]]
* [[AZ-11713908]]
* [[Bunamidine]]

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== References ==
{{reflist}}


{{Cannabinoids}}
{{Cannabinoids}}

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{{cannabinoid-stub}}
[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Naphthalenes]]
[[Category:Naphthalenes]]
[[category:Aromatic ketones]]
[[Category:Aromatic ketones]]
[[category:Naphthol ethers]]
[[Category:Naphthol ethers]]
[[Category:Peripherally selective drugs]]
[[Category:Ethers]]

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{{cannabinoid-stub}}
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