Mepirapim

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]

Mepirapim
Legal status
Legal status
Identifiers
IUPAC name
  • (4-methylpiperazin-1-yl)-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC19H27N3O
Molar mass313.445 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCN1C=C(C2=CC=CC=C21)C(=O)N3CCN(CC3)C
InChI
  • InChI=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
  • Key:IUEFFEOHJKCBPF-UHFFFAOYSA-N

Legality

Sweden's public health agency suggested to classify MEPIRAPIM as hazardous substance on November 10, 2014.[4]

See also

References
  1. "MEPIRAPIM". Cayman Chemical. Retrieved 23 June 2015.
  2. 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.
  3. 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.
  4. "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.


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