MDMB-CHMINACA

MDMB-CHMINACA
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;
UNII	Z6EXBVG316;
CompTox Dashboard (EPA)	DTXSID001010034 ;
Chemical and physical data
Formula	C22H31N3O3
Molar mass	385.508 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]

References

^ 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.
^ "MDMB-CHMINACA". Cayman Chemical. Retrieved 14 July 2015.
^ 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.
^ 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.
^ "Идентификация синтетических каннабимиметиков MDMB-CHMINACA, MDMB-FUBINACA и их метаболитов" (in Russian). CTS "SCIENCE". Retrieved 14 July 2015.
^ 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.
^ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980
^ "Очередная жертва спайса" (in Russian). Federal Drug Control Service of the Russian Federation. 17 March 2015. Archived from the original on 14 July 2015. Retrieved 13 July 2015.
^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 14 July 2015.
^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
^ "Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 25 September 2019.

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[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. Archived from the original on 14 July 2015. Retrieved 13 July 2015.

[9] "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 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.

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Legal status

See also

References