Cannabis Ruderalis

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Importing Wikidata short description: "Chemical compound" (Shortdesc helper)
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| IUPAC_name = N-(naphthalen-1-yl)-1-pentyl-1H-indazole-3-carboxamide
| IUPAC_name = N-(naphthalen-1-yl)-1-pentyl-1H-indazole-3-carboxamide
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = Schedule II
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = Class B
| legal_US =
| legal_US =
| legal_NZ =
| legal_NZ =
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<!--Identifiers-->
<!--Identifiers-->
⚫
| CAS_number_Ref =
| CAS_number = 1391484-80-2
| CAS_number = 1391484-80-2
⚫
| CAS_number_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = GP2N1PG5X2
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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<!--Chemical data-->
<!--Chemical data-->
| C=23 | H=23 | N=3 | O=1
| C=23 | H=23 | N=3 | O=1
| molecular_weight = 357.5 g/mol
}}
}}


'''MN 18''' is an [[indazole]]-based [[synthetic cannabinoid]] that is an [[agonist]] for the [[cannabinoid receptor]]s, with [[enzyme inhibitor|''K''<sub>i</sub>]] values of 45.72&nbsp;nM at [[cannabinoid receptor type 1|CB<sub>1</sub>]] and 11.098&nbsp;nM at [[cannabinoid receptor type 2|CB<sub>2</sub>]] and [[EC50|EC<sub>50</sub>]] values of 2.028&nbsp;nM at CB<sub>1</sub> and 1.233&nbsp;nM at CB<sub>2</sub>,<ref>{{cite journal|first1=Thomas F.|last1=Gamage|first2=Charlotte E.|last2=Farquhar|first3=Timothy W.|last3=Lefever|first4=Julie A.|last4=Marusich|title=Molecular and behavioral pharmacological characterization of abused synthetic cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-fluoro-CUMYL-PICA|url=http://jpet.aspetjournals.org/content/early/2018/03/16/jpet.117.246983|journal=Journal of Pharmacology and Experimental Therapeutics|volume=365|issue=1|date=April 2018|issn=0022-3565|pages=437–446|pmid=29549157|pmc=5932312|doi=10.1124/jpet.117.246983|first5=Richard C.|last5=Kevin|first6=Iain S.|last6=McGregor|first7=Jenny L.|last7=Wiley|first8=Brian F.|last8=Thomas}}</ref> and has been sold online as a [[designer drug]].<ref>{{cite web | url=http://forendex.southernforensic.org/index.php/detail/index/1276 | title=MN-18 | publisher=Southern Association of Forensic Scientists | accessdate=23 July 2015}}</ref><ref name="Uchiyama_2015">{{cite journal | title=A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N–OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products |author1=Nahoko Uchiyama |author2=Yoshihiko Shimokawa |author3=Ruri Kikura-Hanajiri |author4=Yosuke Demizu |author5=Yukihiro Goda |author6=Takashi Hakamatsuka | journal=Forensic Toxicology |date=February 2015 | doi=10.1007/s11419-015-0268-7 | pmid=26257833 | pmc=4525202 | volume=33 |issue = 2| pages=244–259}}</ref> It is the indazole core analogue of [[NNE1]]. Given the known metabolic liberation (and presence as an impurity) of [[amantadine]] in the related compound [[APINACA]], it is suspected that metabolic hydrolysis of the amide group of MN-18 may release [[1-naphthylamine]], a known [[carcinogen]]. MN-18 metabolism has been described in literature.<ref>{{cite journal | author1=Xingxing Diao | url=http://clinchem.aaccjnls.org/content/63/11/1753.long | title=Human Hepatocyte Metabolism of Novel Synthetic Cannabinoids MN-18 and Its 5-Fluoro Analog 5F-MN-18 | date=August 2017 | author2=Jeremy Carlier | author3=Mingshe Zhu | author4=Marilyn A. Huestis | journal=Clinical Chemistry | volume=63 | issue=11 | pages=1753–1763 | doi=10.1373/clinchem.2017.277152| pmid=28821542 }}</ref><ref>{{cite web |title=How CBD Works: The Endocannabinoid System |url=https://www.leafreport.com/education/how-cbd-works-the-endocannabinoid-system-1689 |accessdate=30 October 2019}}</ref><ref>{{cite journal | author1=Richard C. Kevin | title=Kinetic and metabolic profiles of synthetic cannabinoids NNEI and MN-18 | date=August 2017 | author2=Timothy W. Lefever | author3=Rodney W. Snyder | author4=Purvi R. Patel | author5=Thomas F. Gamage | author6=Timothy R. Fennell | author7=Jenny L. Wiley | author8=Iain S. McGregor | author9=Brian F. Thomas | journal=Drug Testing and Analysis | volume=10 | issue=1 | pages=137–147 | doi=10.1002/dta.2262| pmid=28834241 | pmc=5785468 }}</ref>
'''MN 18''' is an [[indazole]]-based [[synthetic cannabinoid]] that is an [[agonist]] for the [[cannabinoid receptor]]s, with [[enzyme inhibitor|''K''<sub>i</sub>]] values of 45.72&nbsp;nM at [[cannabinoid receptor type 1|CB<sub>1</sub>]] and 11.098&nbsp;nM at [[cannabinoid receptor type 2|CB<sub>2</sub>]] and [[EC50|EC<sub>50</sub>]] values of 2.028&nbsp;nM at CB<sub>1</sub> and 1.233&nbsp;nM at CB<sub>2</sub>,<ref>{{cite journal | vauthors = Gamage TF, Farquhar CE, Lefever TW, Marusich JA, Kevin RC, McGregor IS, Wiley JL, Thomas BF | display-authors = 6 | title = Molecular and Behavioral Pharmacological Characterization of Abused Synthetic Cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-Fluoro-CUMYL-PICA | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 365 | issue = 2 | pages = 437–446 | date = May 2018 | pmid = 29549157 | pmc = 5932312 | doi = 10.1124/jpet.117.246983 | url = http://jpet.aspetjournals.org/content/early/2018/03/16/jpet.117.246983 }}</ref> and has been sold online as a [[designer drug]].<ref>{{cite web | url=http://forendex.southernforensic.org/index.php/detail/index/1276 | title=MN-18 | publisher=Southern Association of Forensic Scientists | access-date=23 July 2015 | archive-url=https://web.archive.org/web/20150723222131/http://forendex.southernforensic.org/index.php/detail/index/1276 | archive-date=23 July 2015 | url-status=dead }}</ref><ref name="Uchiyama_2015">{{cite journal | vauthors = Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T | title = N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products | journal = Forensic Toxicology | volume = 33 | issue = 2 | pages = 244–259 | date = February 2015 | pmid = 26257833 | pmc = 4525202 | doi = 10.1007/s11419-015-0268-7 }}</ref> It is the indazole core analogue of [[NNE1]]. Given the known metabolic liberation (and presence as an impurity) of [[amantadine]] in the related compound [[APINACA]], it is suspected that metabolic hydrolysis of the amide group of MN-18 may release [[1-naphthylamine]], a known [[carcinogen]]. MN-18 metabolism has been described in literature.<ref>{{cite journal | vauthors = Diao X, Carlier J, Zhu M, Huestis MA | title = Human Hepatocyte Metabolism of Novel Synthetic Cannabinoids MN-18 and Its 5-Fluoro Analog 5F-MN-18 | journal = Clinical Chemistry | volume = 63 | issue = 11 | pages = 1753–1763 | date = November 2017 | pmid = 28821542 | doi = 10.1373/clinchem.2017.277152 | url = http://clinchem.aaccjnls.org/content/63/11/1753.long | doi-access = free }}</ref><ref>{{cite journal | vauthors = Kevin RC, Lefever TW, Snyder RW, Patel PR, Gamage TF, Fennell TR, Wiley JL, McGregor IS, Thomas BF | display-authors = 6 | title = Kinetic and metabolic profiles of synthetic cannabinoids NNEI and MN-18 | journal = Drug Testing and Analysis | volume = 10 | issue = 1 | pages = 137–147 | date = January 2018 | pmid = 28834241 | pmc = 5785468 | doi = 10.1002/dta.2262 }}</ref>


==Legal status==
==Legal status==
⚫
MN-18 is banned in Sweden.{{when|date=October 2019}}<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/maj/cannabinoider-foreslas-bli-klassificerade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassificerade som hälsofarlig vara | publisher=Folkhälsomyndigheten | date=28 May 2014 | access-date=23 July 2015}}</ref>
⚫
On 15 September 2014 the Turkey government banned the sale of MN-18.<ref>{{cite web | url=http://www.resmigazete.gov.tr/eskiler/2014/10/20141002-5-1.pdf/ | title=Turkish Drug Law List | publisher=Resmi Gazete | date=15 Sep 2014}}</ref>


⚫
== See also ==
⚫
MN-18 is banned in Sweden.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/maj/cannabinoider-foreslas-bli-klassificerade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassificerade som hälsofarlig vara | publisher=Folkhälsomyndigheten | date=28 May 2014 | accessdate=23 July 2015}}</ref>
⚫
On 15 September 2014 the Turkey government banned the sale of MN-18 <ref>{{cite web | url=http://www.resmigazete.gov.tr/eskiler/2014/10/20141002-5-1.pdf/ | title=Turkish Drug Law List | publisher=Resmi Gazete | date=15 Sep 2014}}</ref>

⚫
==See also==
{{div col|colwidth=30em}}
{{div col|colwidth=30em}}
* [[5F-NNE1]]
* [[5F-NNE1]]
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{{Div col end}}
{{Div col end}}


==References==
== References ==
{{reflist}}
{{reflist}}


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[[Category:Indazolecarboxamides]]
[[Category:Indazolecarboxamides]]
[[Category:Naphthoylindazoles]]
[[Category:Naphthoylindazoles]]



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

Latest revision as of 03:43, 13 April 2022

MN-18
Legal status
Legal status
Identifiers
  • N-(naphthalen-1-yl)-1-pentyl-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H23N3O
Molar mass357.457 g·mol−1
3D model (JSmol)
  • CCCCCn1nc(c2c1cccc2)C(=O)Nc1cccc2c1cccc2
  • InChI=1S/C23H23N3O/c1-2-3-8-16-26-21-15-7-6-13-19(21)22(25-26)23(27)24-20-14-9-11-17-10-4-5-12-18(17)20/h4-7,9-15H,2-3,8,16H2,1H3,(H,24,27)
  • Key:UJKHLVOEXULDRU-UHFFFAOYSA-N

MN 18 is an indazole-based synthetic cannabinoid that is an agonist for the cannabinoid receptors, with Ki values of 45.72 nM at CB1 and 11.098 nM at CB2 and EC50 values of 2.028 nM at CB1 and 1.233 nM at CB2,[1] and has been sold online as a designer drug.[2][3] It is the indazole core analogue of NNE1. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of MN-18 may release 1-naphthylamine, a known carcinogen. MN-18 metabolism has been described in literature.[4][5]

Legal status[edit]

MN-18 is banned in Sweden.[when?][6] On 15 September 2014 the Turkey government banned the sale of MN-18.[7]

See also[edit]

References[edit]

  1. ^ Gamage TF, Farquhar CE, Lefever TW, Marusich JA, Kevin RC, McGregor IS, et al. (May 2018). "Molecular and Behavioral Pharmacological Characterization of Abused Synthetic Cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-Fluoro-CUMYL-PICA". The Journal of Pharmacology and Experimental Therapeutics. 365 (2): 437–446. doi:10.1124/jpet.117.246983. PMC 5932312. PMID 29549157.
  2. ^ "MN-18". Southern Association of Forensic Scientists. Archived from the original on 23 July 2015. Retrieved 23 July 2015.
  3. ^ Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (February 2015). "N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products". Forensic Toxicology. 33 (2): 244–259. doi:10.1007/s11419-015-0268-7. PMC 4525202. PMID 26257833.
  4. ^ Diao X, Carlier J, Zhu M, Huestis MA (November 2017). "Human Hepatocyte Metabolism of Novel Synthetic Cannabinoids MN-18 and Its 5-Fluoro Analog 5F-MN-18". Clinical Chemistry. 63 (11): 1753–1763. doi:10.1373/clinchem.2017.277152. PMID 28821542.
  5. ^ Kevin RC, Lefever TW, Snyder RW, Patel PR, Gamage TF, Fennell TR, et al. (January 2018). "Kinetic and metabolic profiles of synthetic cannabinoids NNEI and MN-18". Drug Testing and Analysis. 10 (1): 137–147. doi:10.1002/dta.2262. PMC 5785468. PMID 28834241.
  6. ^ "Cannabinoider föreslås bli klassificerade som hälsofarlig vara". Folkhälsomyndigheten. 28 May 2014. Retrieved 23 July 2015.
  7. ^ "Turkish Drug Law List". Resmi Gazete. 15 Sep 2014.
source: https://en.wikipedia.org/w/index.php?title=MN-18&diff=1082424895&oldid=923701831

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