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Importing Wikidata short description: "Chemical compound" (Shortdesc helper) |
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| CAS_number_Ref = |
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| CAS_number = |
| CAS_number = 2365542-29-4 |
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| ATC_prefix = |
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| PubChem = 101896603 |
| PubChem = 101896603 |
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| ChemSpiderID = 52085735 |
| ChemSpiderID = 52085735 |
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| UNII = W6OZW1T05K |
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| smiles = CCCCCN1C=C(C2=CC=CC=C21)C(=O)N3CCN(CC3)C |
| smiles = CCCCCN1C=C(C2=CC=CC=C21)C(=O)N3CCN(CC3)C |
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| StdInChI = 1S/C19H27N3O/c1-3-4-7-10-22-15-17(16-8-5-6-9-18(16)22)19(23)21-13-11-20(2)12-14-21/h5-6,8-9,15H,3-4,7,10-14H2,1-2H3 |
| StdInChI = 1S/C19H27N3O/c1-3-4-7-10-22-15-17(16-8-5-6-9-18(16)22)19(23)21-13-11-20(2)12-14-21/h5-6,8-9,15H,3-4,7,10-14H2,1-2H3 |
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'''MEPIRAPIM''' is an [[indole]]-based [[cannabinoid]] which differs from [[JWH-018]] by having a 4-methylpiperazine group in place of the naphthyl group<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15388 | title=MEPIRAPIM | publisher=Cayman Chemical | access-date=23 June 2015}}</ref> and has been used as an active ingredient in [[synthetic cannabis]] products. It was first identified in Japan in 2013, alongside [[FUBIMINA]].<ref name="Uchiyama_2014">{{cite journal | title=Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products | journal=Forensic Toxicology | vauthors=Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | date=January 2014 | volume=32 | issue=1 | pages=105–115 | doi=10.1007/s11419-013-0217-2| s2cid=32599561 }}</ref> |
'''MEPIRAPIM''' is an [[indole]]-based [[cannabinoid]] which differs from [[JWH-018]] by having a 4-methylpiperazine group in place of the naphthyl group<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15388 | title=MEPIRAPIM | publisher=Cayman Chemical | access-date=23 June 2015}}</ref> and has been used as an active ingredient in [[synthetic cannabis]] products. It was first identified in Japan in 2013, alongside [[FUBIMINA]].<ref name="Uchiyama_2014">{{cite journal | title=Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products | journal=Forensic Toxicology | vauthors=Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | date=January 2014 | volume=32 | issue=1 | pages=105–115 | doi=10.1007/s11419-013-0217-2| s2cid=32599561 }}</ref> MEPIRAPIM acts as a [[T-type calcium channel ]]inhibitor and is only minimally active at the central CB1 receptor.<ref>{{Cite journal| doi = 10.1021/acschemneuro.1c00822|pmid = 35442021| last1 = Kevin| first1 = Richard C.| last2 = Mirlohi| first2 = Somayeh| last3 = Manning| first3 = Jamie J.| last4 = Boyd| first4 = Rochelle| last5 = Cairns| first5 = Elizabeth A.| last6 = Ametovski| first6 = Adam| last7 = Lai| first7 = Felcia| last8 = Luo| first8 = Jia Lin| last9 = Jorgensen| first9 = William| last10 = Ellison| first10 = Ross| last11 = Gerona| first11 = Roy R.| last12 = Hibbs| first12 = David E.| last13 = McGregor| first13 = Iain S.| last14 = Glass| first14 = Michelle| last15 = Connor| first15 = Mark| last16 = Bladen| first16 = Chris| last17 = Zamponi| first17 = Gerald W.| last18 = Banister| first18 = Samuel D.| title = Putative Synthetic Cannabinoids MEPIRAPIM, 5F-BEPIRAPIM (NNL-2), and Their Analogues Are T-Type Calcium Channel (CaV3) Inhibitors| journal = ACS Chemical Neuroscience| date = April 2022}}</ref> |
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==Legality== |
==Legality== |
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Revision as of 23:18, 20 April 2022
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| Formula | C19H27N3O |
| Molar mass | 313.445 g·mol−1 |
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MEPIRAPIM is an indole-based cannabinoid which differs from JWH-018 by having a 4-methylpiperazine group in place of the naphthyl group[1] and has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in 2013, alongside FUBIMINA.[2] MEPIRAPIM acts as a T-type calcium channel inhibitor and is only minimally active at the central CB1 receptor.[3]
Legality
Sweden's public health agency suggested to classify MEPIRAPIM as hazardous substance on November 10, 2014.[4]
See also
References
- ^ "MEPIRAPIM". Cayman Chemical. Retrieved 23 June 2015.
- ^ Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (January 2014). "Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products". Forensic Toxicology. 32 (1): 105–115. doi:10.1007/s11419-013-0217-2. S2CID 32599561.
- ^ Kevin, Richard C.; Mirlohi, Somayeh; Manning, Jamie J.; Boyd, Rochelle; Cairns, Elizabeth A.; Ametovski, Adam; Lai, Felcia; Luo, Jia Lin; Jorgensen, William; Ellison, Ross; Gerona, Roy R.; Hibbs, David E.; McGregor, Iain S.; Glass, Michelle; Connor, Mark; Bladen, Chris; Zamponi, Gerald W.; Banister, Samuel D. (April 2022). "Putative Synthetic Cannabinoids MEPIRAPIM, 5F-BEPIRAPIM (NNL-2), and Their Analogues Are T-Type Calcium Channel (CaV3) Inhibitors". ACS Chemical Neuroscience. doi:10.1021/acschemneuro.1c00822. PMID 35442021.
- ^ "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.