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MDMB-CHMINACA

MDMB-CHMINACA
MDMB-CHMINACA.svg
Legal status
Legal status
  • CA: Schedule II
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • Illegal in Singapore and Switzerland
Identifiers
IUPAC name
  • Methyl (2S)-2-{[1-(cyclohexylmethyl)-1H-indazol-3-yl]formamido}-3,3-dimethylbutanoate
CAS Number
  • 1185888-32-7
PubChem CID
  • 121491808
ChemSpider
  • 32055574
Chemical and physical data
FormulaC22H31N3O3
Molar mass385.508 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC(C)(C)[C@@H](C(=O)OC)NC(=O)C1=NN(C2=CC=CC=C21)CC3CCCCC3
InChI
  • InChI=1S/C22H31N3O3/c1-22(2,3)19(21(27)28-4)23-20(26)18-16-12-8-9-13-17(16)25(24-18)14-15-10-6-5-7-11-15/h8-9,12-13,15,19H,5-7,10-11,14H2,1-4H3,(H,23,26)/t19-/m1/s1
  • Key:DGQMLBSSRFFINY-LJQANCHMSA-N

MDMB-CHMINACA (also known as MDMB(N)-CHM) is an indazole-based synthetic cannabinoid that acts as a potent agonist of the CB1 receptor,[1] and has been sold online as a designer drug.[2][3][4][5][6] It was invented by Pfizer in 2008, and is one of the most potent cannabinoid agonists known, with a binding affinity of 0.0944 nM at CB1, and an EC50 of 0.330 nM.[7] It is closely related to MDMB-FUBINACA, which caused at least 1000 hospitalizations and 40 deaths in Russia as consequence of intoxication.[8]

Legal status

MDMB-CHMINACA is a Fifth Schedule of the Misuse of Drugs Act (MDA) controlled substance in Singapore as of May 2015.[9]

MDMB-CHMINACA is illegal in Germany, Switzerland as of December 2015.[10]

Sweden's public health agency suggested classifying MDMB-CHMINACA as a hazardous substance, on September 25, 2019.[11]

See also

  • AB-CHMINACA
  • ADB-CHMINACA
  • ADB-FUBINACA
  • MDMB-CHMICA
  • MDMB-FUBINACA
  • PX-3 (APP-CHMINACA)

References

  1. ^ Banister, Samuel D.; Longworth, Mitchell; Kevin, Richard; Sachdev, Shivani; Santiago, Marina; Stuart, Jordyn; Mack, James B. C.; Glass, Michelle; McGregor, Iain S.; Connor, Mark; Kassiou, Michael (2016). "Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues". ACS Chemical Neuroscience. 7 (9): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
  2. ^ "MDMB-CHMINACA". Cayman Chemical. Retrieved 14 July 2015.
  3. ^ Shevyrin, Vadim; Melkozerov, Vladimir; Nevero, Alexander; Eltsov, Oleg; Shafran, Yuri; Morzherin, Yuri; Lebedev, AlbertT. (August 2015). "Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group". Analytical and Bioanalytical Chemistry. 407 (21): 6301–6315. doi:10.1007/s00216-015-8612-7. ISSN 1618-2642. PMID 25893797.
  4. ^ Prof. SA Savchuk (2014). "Detection methods of psychoactive substances and liquid chromotograoghy detection of metabolites" (PDF) (in Russian). Russian Ministry of Health. Retrieved 14 July 2015.
  5. ^ "Идентификация синтетических каннабимиметиков MDMB-CHMINACA, MDMB-FUBINACA и их метаболитов" (in Russian). CTS "SCIENCE". Retrieved 14 July 2015.
  6. ^ Hess, Cornelius; Murach, Jacqueline; Krueger, Lynn; Scharrenbroch, Lisa; Unger, Michael; Madea, Burkhard; Sydow, Konrad (2016). "Simultaneous detection of 93 synthetic cannabinoids by liquid chromatography-tandem mass spectrometry and retrospective application to real forensic samples". Drug Testing and Analysis. 9 (5): 721–733. doi:10.1002/dta.2030. ISSN 1942-7611. PMID 27400642.
  7. ^ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980
  8. ^ "Очередная жертва спайса" (in Russian). Federal Drug Control Service of the Russian Federation. 17 March 2015. Retrieved 13 July 2015.
  9. ^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Retrieved 14 July 2015.
  10. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
  11. ^ "Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 25 September 2019.
Cannabinoids
Phytocannabinoids
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  • Gallocatechol
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  • THC-C4
  • THCA
  • THCV
  • Yangonin
  • Active metabolites:
  • 11-COOH-THC
  • 11-OH-THC
Endocannabinoids
  • 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)
  • N-Arachidonoyl serotonin (AA-5-HT)
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Synthetic
cannabinoids
Classical cannabinoids
(dibenzopyrans)
  • A-40174
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  • O-2545
  • O-2694
  • Parahexyl
  • Pirnabine
  • THC-O-acetate
  • THC-O-phosphate
Non-classical
cannabinoids
  • Cannabicyclohexanol
  • CBD-DMH
  • CP 47,497
  • (C6)-CP 47,497
  • (C9)-CP 47,497
  • CP 55,244
  • CP 55,940
  • HU-308
  • HU-320
  • HU-331
  • HU-336
  • HU-345
  • HUF-101
  • Nonabine
  • O-1871
  • Tinabinol
Benzoylindoles
  • AM-630
  • AM-679
  • AM-694
  • AM-1241
  • AM-2233
  • GW-405,833 (L-768,242)
  • Pravadoline
  • RCS-4
  • WIN 54,461
Naphthoylindoles
  • AM-1220
  • AM-1221
  • AM-1235
  • AM-2201
  • AM-2232
  • EAM-2201
  • FUB-JWH-018
  • JWH-007
  • JWH-015
  • JWH-018
  • JWH-019
  • JWH-073
  • JWH-081
  • JWH-098
  • JWH-116
  • JWH-122
  • JWH-149
  • JWH-164
  • JWH-182
  • JWH-193
  • JWH-198
  • JWH-200
  • JWH-210
  • JWH-398
  • JWH-424
  • MAM-2201
  • NE-CHMIMO
Naphthoylindazoles
  • THJ-018
  • THJ-2201
Pyrrolobenzoxazines
  • WIN 55,212-2
Naphthylmethylindoles
  • JWH-175
  • JWH-176
  • JWH-184
  • JWH-185
  • JWH-196
Phenylacetylindoles
  • Cannabipiperidiethanone
  • JWH-167
  • JWH-203
  • JWH-249
  • JWH-250
  • JWH-251
  • JWH-302
  • RCS-8
Indole-3-carboxamides
  • 5F-ADBICA
  • 5F-MDMB-PICA
  • 5F-NNE1
  • 5F-PCN
  • 5F-SDB-006
  • AB-FUBICA
  • AB-PICA
  • ADBICA
  • ADB-FUBICA
  • APICA
  • CUMYL-PICA
  • FDU-NNE1
  • MDMB-CHMICA
  • MMB-CHMICA
  • MMB-2201
  • MN-25 (UR-12)
  • NNE1
  • PX-1
  • Org 28312
  • Org 28611
  • SDB-006
  • STS-135
Indole-3-carboxylates
  • 5F-PB-22
  • FDU-PB-22
  • FUB-PB-22
  • QUCHIC (BB-22)
  • QUPIC (PB-22)
  • NM-2201
Tetramethylcyclo-
propanoylindoles
  • A-796,260
  • A-834,735
  • FUB-144
  • UR-144
  • XLR-11
  • XLR-12
Indazole-3-
carboxamides
  • 5F-ADB
  • 5F-ADB-PINACA
  • 5F-AMB
  • 5F-APINACA
  • 5F-CUMYL-PINACA
  • 5F-EDMB-PINACA
  • 5F-EMB-PINACA
  • AB-CHMINACA
  • AB-FUBINACA
  • AB-PINACA
  • ADB-CHMINACA
  • ADB-FUBINACA
  • ADB-PINACA
  • Adamantyl-THPINACA
  • ADSB-FUB-187
  • AMB-CHMINACA
  • AMB-FUBINACA
  • APINACA (AKB48)
  • APP-FUBINACA
  • CUMYL-4CN-BINACA
  • CUMYL-PINACA
  • CUMYL-THPINACA
  • FUB-APINACA
  • MDMB-FUBINACA
  • MDMB-CHMINACA
  • MN-18
  • PX-2
  • PX-3
Tetramethylcyclo-
propanoylindazoles
  • FAB-144
Naphthoylpyrroles
  • JWH-030
  • JWH-147
  • JWH-307
Eicosanoids
  • ACEA
  • ACPA
  • Methanandamide (AM-356)
  • O-1812
Pyrazolecarboxamides
  • 5F-AB-FUPPYCA
  • AB-CHFUPYCA
Others
  • 2F-QMPSB
  • 4-HTMPIPO
  • A-836,339
  • Abnormal cannabidiol
  • AB-001
  • BzODZ-EPyr
  • AM-1248
  • AM-1714
  • AZ-11713908
  • AZD-1940
  • BAY 38-7271
  • BAY 59-3074
  • BIM-018
  • CB-13
  • CBS-0550
  • 5F-CUMYL-P7AICA
  • CUMYL-PEGACLONE
  • FUBIMINA
  • GW-842,166X
  • JTE 7-31
  • LASSBio-881
  • LBP-1
  • Leelamine
  • MDA-19
  • MEPIRAPIM
  • NESS-040C5
  • NMP-7
  • O-1269
  • O-1602
  • Olorinab
  • PF-03550096
  • PSB-SB-1202
  • PTI-1
  • PTI-2
  • QMPSB
  • S-444,823
  • SER-601
  • Tedalinab
  • WIN 56,098
Allosteric CBR ligands
  • Org 27569
  • RTI-371
  • Pregnenolone
Endocannabinoid
enhancers

(inactivation inhibitors)
  • 4-Nonylphenylboronic acid
  • AM-404
  • Arachidonoyl serotonin
  • BIA 10-2474
  • Biochanin A
  • Genistein
  • Guineesine
  • IDFP
  • JNJ-42165279
  • JZL184
  • JZL195
  • Kaempferol
  • LY-2183240
  • MK-4409
  • Oleoylethanolamide (OEA)
  • Palmitoylethanolamide (PEA)
  • PF-04457845
  • PF-3845
  • URB-597
  • URB-602
  • URB-754
  • VDM-11
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
  • AM-251
  • AM-630
  • AM-6545
  • BML-190
  • Drinabant (AVE1625)
  • Hemopressin
  • Ibipinabant (SLV319)
  • JTE-907
  • LY-320,135
  • MK-9470
  • NESS-0327
  • O-1918
  • O-2050
  • 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
Cannabinoid receptor modulators
Receptor
(ligands)
CB1
  • Agonists (abridged; see here for more): 2-AG
  • 2-AGE (noladin ether)
  • 11-Hydroxy-THC
  • α-Amyrin · β-Amyrin
  • AB-CHMINACA
  • AM-1220
  • AM-1221
  • AM-1235
  • AM-2201
  • AM-2232
  • Anandamide
  • AZ-11713908
  • Cannabinol
  • CB-13
  • CP 47,497
  • CP 55,940
  • Dimethylheptylpyran
  • DEA
  • ECG
  • EGCG
  • Epicatechin
  • Gallocatechol (gallocatechin)
  • Honokiol
  • HU-210
  • JWH-007
  • JWH-015
  • JWH-018
  • JWH-073
  • Kavain
  • L-759,633
  • Levonantradol
  • Menabitan
  • Nabilone
  • Nabitan
  • NADA
  • O-1812
  • Oleamide
  • Pravadoline
  • Serinolamide A
  • THC (dronabinol)
  • UR-144
  • WIN 55,212-2
  • Yangonin
  • Antagonists: AM-251
  • AM-6545
  • Cannabidiol
  • Cannabigerol
  • Drinabant
  • Falcarinol (carotatoxin)
  • Hemopressin
  • Ibipinabant
  • LY-320,135
  • MK-9470
  • NESS-0327
  • O-2050
  • Otenabant
  • PF-514273
  • PipISB
  • Rimonabant
  • Rosonabant
  • Surinabant
  • Taranabant
  • THCV
  • TM-38837
  • VCHSR
  • Virodhamine
  • Antibodies:
  • Unknown/unsorted: MAFP
CB2
  • Agonists: 2-AG
  • 2-AGE (noladin ether)
  • 3,3'-Diindolylmethane
  • 4-O-Methylhonokiol
  • α-Amyrin · β-Amyrin
  • A-796,260
  • A-834,735
  • A-836,339
  • AM-1221
  • AM-1235
  • AM-1241
  • AM-2232
  • Anandamide
  • AZ-11713908
  • Cannabinol
  • Caryophyllene
  • CB-13
  • CBS-0550
  • CP 55,940
  • GW-405,833 (L-768,242)
  • GW-842,166X
  • HU-308
  • JTE 7-31
  • JWH-007
  • JWH-015
  • JWH-018
  • JWH-133
  • L-759,633
  • L-759,656
  • Magnolol
  • MDA-19
  • Nabitan
  • NADA
  • Olorinab (APD-371)
  • PF-03550096
  • S-444,823
  • SER-601
  • Serinolamide A
  • UR-144
  • Tedalinab
  • THC (dronabinol)
  • THCV
  • Virodhamine
  • Antagonists: 4-O-Methylhonokiol
  • AM-630
  • BML-190
  • Cannabidiol
  • Honokiol
  • JTE-907
  • SR-144,528
  • WIN 54,461
  • WIN 56,098
NAGly
(GPR18)
  • Agonists: Abnormal cannabidiol
  • ACPA
  • AM251
  • Anandamide
  • Cannabidiol
  • NADGly
  • THC (dronabinol)
  • O-1602
  • Antagonists: CID-85469571
  • O-1918
GPR55
  • Agonists: 2-AGE (noladin ether)
  • Abnormal cannabidiol
  • AM-251
  • CP 55,940
  • Lysophosphatidylinositol
  • O-1602
  • Oleoylethanolamide
  • Palmitoylethanolamide
  • THC (dronabinol)
  • Antagonists: Cannabidiol
  • CID-16020046
  • O-1918
  • PSB-SB-487
  • PSB-SB-1202
GPR119
  • Agonists: 2-Oleoylglycerol
  • Anandamide
  • AR-231,453
  • Oleoylethanolamide
  • PSN-375,963
  • PSN-632,408
Unsorted
  • Agonists:
Transporter
(modulators)
eCBTs
  • Inhibitors:
  • AM-404
  • Arachidonoyl serotonin
  • Cannabidiol
  • Guineensine
  • LY-2183240
  • Paracetamol (acetaminophen)
  • URB-597
  • VDM-11
Enzyme
(modulators)
FAAH
  • Inhibitors: 4-Nonylphenylboronic acid
  • AACOCF3
  • AM-404
  • Arachidonoyl serotonin
  • BIA 10-2474
  • Biochanin A
  • Genistein
  • IDFP
  • JNJ-42165279
  • JZL-195
  • Kaempferol
  • LY-2183240
  • MAFP
  • Paracetamol (acetaminophen)
  • PF-3845
  • PF-04457845
  • URB-597
  • Activators:
MAGL
  • Inhibitors:
  • IDFP
  • JZL-184
  • JZL-195
  • MAFP
  • URB-602
ABHD6
  • Inhibitors:
ABHD12
  • Inhibitors: Betulinic acid
  • Maslinic acid
  • MAFP
  • Oleanolic acid
  • Orlistat (tetrahydrolipstatin)
  • Ursolic acid
Others
  • Precursors: Phosphatidylethanolamine
  • NAPE
  • Diacylglycerol
  • Others: (directly potentiates activity of 2-AG at CB1 receptor)
  • (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)


source: http://en.wikipedia.org/wiki/MDMB-CHMINACA
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