Cannabis Ruderalis

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'''CB-13''' ('''CRA13''', '''SAB-378''')<ref>{{Cite journal | last1 = Cluny | first1 = N. L. | last2 = Keenan | first2 = C. M. | last3 = Duncan | first3 = M. | last4 = Fox | first4 = A. | last5 = Lutz | first5 = B. | last6 = Sharkey | first6 = K. A. | doi = 10.1124/jpet.110.169946 | 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 = Journal of Pharmacology and Experimental Therapeutics | volume = 334 | issue = 3 | pages = 973–80 | year = 2010 | pmid = 20571060| 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 | last1 = Dziadulewicz | first1 = E. K. | last2 = Bevan | first2 = S. J. | last3 = Brain | first3 = C. T. | last4 = Coote | first4 = P. R. | last5 = Culshaw | first5 = A. J. | last6 = Davis | first6 = A. J. | last7 = Edwards | first7 = L. J. | last8 = Fisher | first8 = A. J. | last9 = Fox | first9 = A. J. | last10 = Gentry | doi = 10.1021/jm070317a | first10 = C. | last11 = Groarke | first11 = A. | last12 = Hart | first12 = T. W. | last13 = Huber | first13 = W. | last14 = James | first14 = I. F. | last15 = Kesingland | first15 = A. | last16 = La Vecchia | first16 = L. | last17 = Loong | first17 = Y. | last18 = Lyothier | first18 = I. | last19 = McNair | first19 = K. | last20 = O'Farrell | first20 = C. | last21 = Peacock | first21 = M. | last22 = Portmann | first22 = R. | last23 = Schopfer | first23 = U. | last24 = Yaqoob | first24 = M. | last25 = Zadrobilek | first25 = J. | title = Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: A Potent, Orally Bioavailable Human CB1/CB2Dual Agonist with Antihyperalgesic Properties and Restricted Central Nervous System Penetration | journal = Journal of Medicinal Chemistry | volume = 50 | issue = 16 | pages = 3851–3856 | year = 2007 | pmid = 17630726}}</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=827–33 |date=April 2009 |pmid=19144772 |doi=10.1124/dmd.108.024000 |s2cid=15150118 }}</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==
==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 | 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>
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>


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
⚫
==See also==
| date = 3 January 2023 }}</ref>

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


==References==
== References ==
{{reflist}}
<references/>


{{Cannabinoids}}
{{Cannabinoids}}
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[[Category:Naphthol ethers]]
[[Category:Naphthol ethers]]
[[Category:Peripherally selective drugs]]
[[Category:Peripherally selective drugs]]
[[Category:Diaryl ethers]]
[[Category:Ethers]]



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

Latest revision as of 06:17, 20 February 2024

CB-13
Legal status
Legal status
Identifiers
  • Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H24O2
Molar mass368.476 g·mol−1
3D model (JSmol)
  • c13ccccc1cccc3C(=O)c4ccc(OCCCCC)c2ccccc24
  • InChI=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
  • Key:RSUMDJRTAFBISX-UHFFFAOYSA-N
  (verify)

CB-13 (CRA13, SAB-378)[1] is a cannabinoid drug, which acts as a potent agonist at both the CB1 and CB2 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 antihyperalgesic properties in animal studies,[2] and has progressed to preliminary human trials.[3]

Legal Status[edit]

As of October 2015 CB-13 is a controlled substance in China.[4]

CB-13 is a Schedule I controlled substance in North Dakota.[5]

See also[edit]

References[edit]

  1. ^ Cluny NL, Keenan CM, Duncan M, Fox A, Lutz B, Sharkey KA (September 2010). "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". The Journal of Pharmacology and Experimental Therapeutics. 334 (3): 973–980. doi:10.1124/jpet.110.169946. PMID 20571060. S2CID 9198992.
  2. ^ Dziadulewicz EK, Bevan SJ, Brain CT, Coote PR, Culshaw AJ, Davis AJ, et al. (August 2007). "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. 50 (16): 3851–3856. doi:10.1021/jm070317a. PMID 17630726.
  3. ^ Gardin A, Kucher K, Kiese B, Appel-Dingemanse S (April 2009). "Cannabinoid receptor agonist 13, a novel cannabinoid agonist: first in human pharmacokinetics and safety". Drug Metabolism and Disposition. 37 (4): 827–833. doi:10.1124/dmd.108.024000. PMID 19144772. S2CID 15150118.
  4. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  5. ^ "Schedule 1" (PDF). Sixty-eighth Legislative Assembly of North Dakota. 3 January 2023.
source: https://en.wikipedia.org/w/index.php?title=CB-13&diff=1209082790&oldid=1101205338

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