MDMB-CHMINACA

Last updated

MDMB-CHMINACA
MDMB-CHMINACA.svg
Legal status
Legal status
Identifiers
  • Methyl (2S)-2-{[1-(cyclohexylmethyl)-1H-indazol-3-yl]formamido}-3,3-dimethylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H31N3O3
Molar mass 385.508 g·mol−1
3D model (JSmol)
  • CC(C)(C)[C@@H](C(=O)OC)NC(=O)C1=NN(C2=CC=CC=C21)CC3CCCCC3
  • 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]

Contents

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]

See also

References

  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. Archived from the original on 31 October 2019. Retrieved 11 November 2019.