Mepirapim

Mepirapim
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name (4-methylpiperazin-1-yl)-(1-pentylindol-3-yl)methanone;
CAS Number	2365542-29-4;
PubChem CID	101896603;
ChemSpider	52085735;
UNII	W6OZW1T05K;
CompTox Dashboard (EPA)	DTXSID901032510 ;
Chemical and physical data
Formula	C19H27N3O
Molar mass	313.445 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

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 RC, Mirlohi S, Manning JJ, Boyd R, Cairns EA, Ametovski A, et al. (May 2022). "Putative Synthetic Cannabinoids MEPIRAPIM, 5F-BEPIRAPIM (NNL-2), and Their Analogues Are T-Type Calcium Channel (Ca_V3) Inhibitors". ACS Chemical Neuroscience. 13 (9): 1395–1409. doi:10.1021/acschemneuro.1c00822. PMID 35442021. S2CID 248264685.
^ "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.

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[1] "MEPIRAPIM". Cayman Chemical. Retrieved 23 June 2015.

[Uchiyama_2014-2] 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 RC, Mirlohi S, Manning JJ, Boyd R, Cairns EA, Ametovski A, et al. (May 2022). "Putative Synthetic Cannabinoids MEPIRAPIM, 5F-BEPIRAPIM (NNL-2), and Their Analogues Are T-Type Calcium Channel (Ca_V3) Inhibitors". ACS Chemical Neuroscience. 13 (9): 1395–1409. doi:10.1021/acschemneuro.1c00822. PMID 35442021. S2CID 248264685.

[4] "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.

[1]

[2]

[3]

[4]

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name (4-methylpiperazin-1-yl)-(1-pentylindol-3-yl)methanone
CAS Number	2365542-29-4
PubChem CID	101896603
ChemSpider	52085735
UNII	W6OZW1T05K
CompTox Dashboard (EPA)	DTXSID901032510
Chemical and physical data
Formula	C₁₉H₂₇N₃O
Molar mass	313.445 g·mol⁻¹
3D model (JSmol)	Interactive image
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

Mepirapim

Legality

See also

References