MDMB-CHMINACA

MDMB-CHMINACA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; 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^[1] (also known as MDMB(N)-CHM) is an indazole-based synthetic cannabinoid that acts as a potent agonist of the CB₁ receptor,^[2] and has been sold online as a designer drug.^[3]^[4]^[5]^[6]^[7] 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.^[8] It is closely related to MDMB-FUBINACA, which caused at least 1000 hospitalizations and 40 deaths in Russia as consequence of intoxication.^[9]

Legal status

MDMB-CHMINACA is a Fifth Schedule of the Misuse of Drugs Act (MDA) controlled substance in Singapore as of May 2015.^[10]

MDMB-CHMINACA is illegal in Germany, Switzerland as of December 2015.^[11]

Sweden's public health agency suggested classifying MDMB-CHMINACA as a hazardous substance, on September 25, 2019.^[12]

References

^ Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
^ Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 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 V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, et al. (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): 6301–15. doi:10.1007/s00216-015-8612-7. PMID 25893797. S2CID 31838655.
^ Savchuk SA (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" [Identification of synthetic cannabimimetics MDMB-CHMINACA, MDMB-FUBINACA and their metabolites] (in Russian). CTS "SCIENCE". Retrieved 14 July 2015.
^ Hess C, Murach J, Krueger L, Scharrenbroch L, Unger M, Madea B, et al. (May 2017). "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. PMID 27400642.
^ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980
^ "Очередная жертва спайса" [Another victim of spice] (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" [Thirteen substances are proposed to be classified as narcotics or dangerous goods] (in Swedish). Folkhälsomyndigheten (The Public Health Authority). 25 September 2019.

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

[1] Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.

[2] Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 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.

[3] "MDMB-CHMINACA". Cayman Chemical. Retrieved 14 July 2015.

[4] Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, et al. (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): 6301–15. doi:10.1007/s00216-015-8612-7. PMID 25893797. S2CID 31838655.

[5] Savchuk SA (2014). "Detection methods of psychoactive substances and liquid chromotograoghy detection of metabolites" (PDF) (in Russian). Russian Ministry of Health. Retrieved 14 July 2015.

[6] "Идентификация синтетических каннабимиметиков MDMB-CHMINACA, MDMB-FUBINACA и их метаболитов" [Identification of synthetic cannabimimetics MDMB-CHMINACA, MDMB-FUBINACA and their metabolites] (in Russian). CTS "SCIENCE". Retrieved 14 July 2015.

[7] Hess C, Murach J, Krueger L, Scharrenbroch L, Unger M, Madea B, et al. (May 2017). "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. PMID 27400642.

[8] Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980

[9] "Очередная жертва спайса" [Another victim of spice] (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.

[10] "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 14 July 2015.

[11] "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.

[12] "Tretton ämnen föreslås klassas som narkotika eller hälsofarlig vara" [Thirteen substances are proposed to be classified as narcotics or dangerous goods] (in Swedish). Folkhälsomyndigheten (The Public Health Authority). 25 September 2019.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B 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

Legal status

See also

References

€4.95