Mepirapim
Chemical compound
- CA: Schedule II
- DE: NpSG (Industrial and scientific use only)
- UK: Class B
- (4-methylpiperazin-1-yl)-(1-pentylindol-3-yl)methanone
- 2365542-29-4
- 101896603
- 52085735
- W6OZW1T05K
- DTXSID901032510
- Interactive image
- 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]
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 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 (CaV3) 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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(comparison)
Cannabibutols |
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Cannabichromenes | |
Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
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Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics
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