MDMB-CHMICA: Difference between revisions

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| legal_UK =
| legal_UK =
| legal_US =
| legal_US =
| legal_status = Illegal in Austria, China, Louisiana, Sweden & Switzerland
| legal_status = Illegal in Austria, China, Croatia, Denmark, Estonia, Finland, Greece, Hungary, Latvia, Lithuania, Louisiana, Luxembourg, Norway, Poland, Turkey, Sweden & Switzerland<ref name="EMCDDA"/>
| routes_of_administration =
| routes_of_administration =


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| ATC_suffix =
| ATC_suffix =
| PubChem =
| PubChem =
| ChemSpiderID = 34450863
| ChemSpiderID = 34450863
| smiles = COC(=O)[C@@H](NC(=O)c1cn(CC2CCCCC2)c3ccccc13)C(C)(C)C
| smiles = COC(=O)[C@@H](NC(=O)c1cn(CC2CCCCC2)c3ccccc13)C(C)(C)C
| StdInChI = 1S/C23H32N2O3/c1-23(2,3)20(22(27)28-4)24-21(26)18-15-25(14-16-10-6-5-7-11-16)19-13-9-8-12-17(18)19/h8-9,12-13,15-16,20H,5-7,10-11,14H2,1-4H3,(H,24,26)/t20-/m1/s1
| StdInChI = 1S/C23H32N2O3/c1-23(2,3)20(22(27)28-4)24-21(26)18-15-25(14-16-10-6-5-7-11-16)19-13-9-8-12-17(18)19/h8-9,12-13,15-16,20H,5-7,10-11,14H2,1-4H3,(H,24,26)/t20-/m1/s1
| StdInChIKey = SRJKCVHWIDFUBO-HXUWFJFHSA-N
| StdInChIKey = SRJKCVHWIDFUBO-HXUWFJFHSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII =
| UNII =
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}}
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'''MDMB-CHMICA''' (also incorrectly known as '''MMB-CHMINACA''') is an [[indole]]-based [[synthetic cannabinoid]] that is a potent [[agonist]] of the [[CB1 receptor|CB<sub>1</sub> receptor]] and has been sold online as a [[designer drug]].<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/16965 | title=MDMB-CHMICA | publisher=Cayman Chemical | accessdate=29 June 2015}}</ref><ref>{{cite web | url=http://forendex.southernforensic.org/index.php/detail/index/1305 | title=MDMB-CHMICA | publisher=Southern Association of Forensic Scientists | accessdate=29 June 2015}}</ref> While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue of [[MDMB-CHMINACA]]) has been identified on the designer drug market in 2015 as "AMB-CHMINACA" or "MA-CHMINACA".<ref name="Shevyrin_2015">{{cite journal | vauthors = Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT | title = Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group | journal = Analytical and Bioanalytical Chemistry | date = April 2015 | pmid = 25893797 | doi = 10.1007/s00216-015-8612-7 | url = http://link.springer.com/article/10.1007%2Fs00216-015-8612-7 | volume=407 | pages=6301–6315}}</ref>
'''MDMB-CHMICA''' (also incorrectly known as '''MMB-CHMINACA''') is an [[indole]]-based [[synthetic cannabinoid]] that is a potent [[agonist]] of the [[Cannabinoid receptor type 1|CB<sub>1</sub> receptor]] and has been sold online as a [[designer drug]].<ref name="EMCDDA"/><ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/16965 | title=MDMB-CHMICA | publisher=Cayman Chemical | accessdate=29 June 2015}}</ref><ref>{{cite web | url=http://forendex.southernforensic.org/index.php/detail/index/1305 | title=MDMB-CHMICA | publisher=Southern Association of Forensic Scientists | accessdate=29 June 2015}}</ref> While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue of [[MDMB-CHMINACA]]) has been identified on the designer drug market in 2015 as [[AMB-CHMINACA]].<ref>{{cite journal|first1=Vadim|last1=Shevyrin|first2=Vladimir|last2=Melkozerov|first3=Alexander|last3=Nevero|first4=Oleg|last4=Eltsov|title=Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group|url=http://link.springer.com/article/10.1007/s00216-015-8612-7|journal=Analytical and Bioanalytical Chemistry|date=August 2015|pages=6301–6315|volume=407|issue=21|doi=10.1007/s00216-015-8612-7|pmid=25893797|first5=Yuri|last5=Shafran|first6=Yuri|last6=Morzherin|first7=Albert T.|last7=Lebedev}}</ref>


== Seizures ==
40&nbsp;kg of MDMB-CHMICA was seized in Luxembourg in December 2014.<ref>{{cite web | url=https://www.unodc.org/documents/scientific/Global_SMART_Update_13_web.pdf | title=Global SMART update | publisher=United Nations Office on Drugs and Crime | date=13 March 2015 | accessdate=29 June 2015}}</ref>

Over 3600 MDMB-CHMICA seizures between 2014 and 2016 in 19 member states of the European Union have been reported to the [[European Monitoring Centre for Drugs and Drug Addiction]] (EMCDDA),<ref name="EMCDDA">{{cite web | url=http://www.emcdda.europa.eu/system/files/publications/2873/2016.4528_WEB.pdf | title=EMCDDA–Europol Joint Report on MDMB-CHMICA | publisher=European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) | date=July 2016 | doi=10.2810/08132 | isbn=978-92-9168-925-5}}</ref> including a 40&nbsp;kg seizure in Luxembourg in December 2014.<ref>{{cite web | url=https://www.unodc.org/documents/scientific/Global_SMART_Update_13_web.pdf | title=Global SMART update | publisher=United Nations Office on Drugs and Crime | date=13 March 2015 | accessdate=29 June 2015}}</ref>


== Chemistry ==
== Chemistry ==
Several commercial samples of MDMB-CHMICA were found to exclusively contain the (''S'')-enantiomer based on vibrational and electronic circular dichroism spectroscopy and X-ray crystallography.<ref>{{cite journal | author1=Lars Andernach | url=http://link.springer.com/article/10.1007/s11419-016-0321-1 | title=Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products | date=June 2016 | author2=Stefan Pusch | author3=Carina Weber | author4=Dieter Schollmeyer | author5=Sascha Münster-Müller | author6=Michael Pütz | author7=Till Opatz | journal=Forensic Toxicology | pages=1–9 | doi=10.1007/s11419-016-0321-1}}</ref> An (S)-configuration for the ''tert''-leucinate group is unsurprising since MDMB-CHMICA is likely synthesized from the abundant and inexpensive "L" form of the appropriate ''tert''-leucinate reactant.
Several commercial samples of MDMB-CHMICA were found to exclusively contain the (''S'')-enantiomer based on vibrational and electronic circular dichroism spectroscopy and X-ray crystallography.<ref>{{cite journal|first1=Lars|last1=Andernach|first2=Stefan|last2=Pusch|first3=Carina|last3=Weber|first4=Dieter|last4=Schollmeyer|title=Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products|url=http://link.springer.com/article/10.1007/s11419-016-0321-1|journal=Forensic Toxicology|date=1 June 2016|pages=344–352|volume=34|issue=2|doi=10.1007/s11419-016-0321-1|first5=Sascha|last5=Münster-Müller|first6=Michael|last6=Pütz|first7=Till|last7=Opatz}}</ref> An (S)-configuration for the ''tert''-leucinate group is unsurprising since MDMB-CHMICA is likely synthesized from the abundant and inexpensive "L" form of the appropriate ''tert''-leucinate reactant.


== Side Effects ==
== Pharmacology ==
There have been a number of reported cases of deaths and hospitalizations in relation to this synthetic cannabinoid.<ref>{{cite web | url=https://forum.goeg.at/EwsForum/default.aspx?g=posts&t=209 | title=[EWS Alert]: 2 deaths and 3 non-fatal intoxications in Germany associated with MDMB-CHMICA (methyl-2-(1-(cyclohexylmethyl)-1 H-indol-3-ylcarbonylamino)-3,3-dimethylbutanoate) | publisher=EMCDDA | date=27 April 2015 | accessdate=29 June 2015}}</ref><ref>{{cite web | url=http://www.bbc.com/news/uk-england-derbyshire-32477643 | title=Derby legal high confusion prompts police warning | publisher=BBC | date=29 April 2015 | accessdate=29 June 2015}}</ref><ref>{{cite web | url=http://www.talkingdrugs.org/drug-alert-dangerous-synthetic-cannabinoid-mmb-chminaca-causing-hospitalizations-deaths-in-europe | title=Drug Alert: Dangerous Synthetic Cannabinoid MMB-CHMINACA Causing Hospitalizations, Deaths in Europe | publisher=TalkingDrugs | date=2 July 2015 | accessdate=2 July 2015}}</ref><ref>{{cite journal | url=http://jat.oxfordjournals.org/content/40/1/86 | title=Sudden Cardiac Death Following Use of the Synthetic Cannabinoid MDMB-CHMICA |author1=Andreas Austgulen Westin |author2=Joachim Frost |author3=Wenche Rødseth Brede |author4=Per Ole M. Gundersen |author5=Steinar Einvik |author6=Harald Aarset |author7=Lars Slørdal | journal=Journal of Analytical Toxicology | date=February 2016 | volume=40 | issue=1 | pages=86–87 | doi=10.1093/jat/bkv110 | pmid=26353925}}</ref><ref>{{cite journal | author1=Alice Seywright | url=http://www.tandfonline.com/doi/abs/10.1080/15563650.2016.1186805 | title=Analysis and clinical findings of cases positive for the novel synthetic cannabinoid receptor agonist MDMB-CHMICA | date=May 2016 | author2=Hazel J. Torrance | author3=Fiona M. Wylie | author4=Denise A. McKeown | author5=David J. Lowe | author6=Richard Stevenson | journal=Clinical Toxicology | pages=1–6 | doi=10.1080/15563650.2016.1186805 | pmid=27213960}}</ref><ref>{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0379073816300469 | title=Fatal intoxication with synthetic cannabinoid MDMB-CHMICA | author=Piotr Adamowicz | journal=Forensic Science International | date=April 2016 | volume=261 | pages=e5–e10 | doi=10.1016/j.forsciint.2016.02.024 | pmid=26934903}}</ref><ref>{{cite journal | url=http://www.tandfonline.com/doi/abs/10.1080/15563650.2016.1190980 | title=Clinical toxicity following analytically confirmed use of the synthetic cannabinoid receptor agonist MDMB-CHMICA. A report from the Identification Of Novel psychoActive substances (IONA) study | date=June 2016 | author=Simon L. Hill, Javad Najafi, Michael Dunn, Paul Acheampong, Ashraf Kamour, Johann Grundlingh, Peter G. Blain, Simon H. L. Thomas | journal=Clinical Toxicology | pages=1–6 | doi=10.1080/15563650.2016.1190980 | pmid=27251903}}</ref>


MDMB-CHMICA acts as a highly potent full [[agonist]] of the [[Cannabinoid receptor type 1|CB<sub>1</sub> receptor]] with an [[Intrinsic activity|efficacy]] of 94% and an [[EC50|EC<sub>50</sub>]] value of 0.14 nM, which is approximately 8 times lower than the EC<sub>50</sub> of [[JWH-018]] (1.13 nM) and twofold lower than [[AB-CHMINACA]] (0.27 nM).<ref name="EMCDDA"/><ref>{{cite journal|first1=Nico|last1=Langer|first2=Rainer|last2=Lindigkeit|first3=Hans-Martin|last3=Schiebel|first4=Uli|last4=Papke|title=Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015|url=http://link.springer.com/article/10.1007/s11419-015-0292-7|journal=Forensic Toxicology|date=8 October 2015|pages=94–107|volume=34|issue=1|doi=10.1007/s11419-015-0292-7|first5=Ludger|last5=Ernst|first6=Till|last6=Beuerle}}</ref>
== Metabolism ==
MDMB-CHMICA appears to have a similar metabolic fate as [[AB-CHMINACA]].<ref>{{cite journal | url=https://www.gtfch.org/cms/images/stories/media/tb/tb2015/Franz_et_al_2015.pdf | title=Metabolism and urine analysis of the new synthetic cannabinoid MDMB-CHMICA |author1=Florian Franz |author2=Nadja Schwörer |author3=Verena Angerer |author4=Bjoern Moosmann |author5=Volker Auwärter | journal=Toxichem Krimtech | date=2015 | volume=82 | pages=192}}</ref>


== Legal status ==
=== Metabolism ===
MDMB-CHMICAs main metabolic reactions comprise mono-hydroxylations and hydrolysis of the carboxylic ester function. In total, 31 metabolites could be identified in vivo.<ref>{{cite journal | url=https://www.gtfch.org/cms/images/stories/media/tb/tb2015/Franz_et_al_2015.pdf | title=Metabolism and urine analysis of the new synthetic cannabinoid MDMB-CHMICA |author1=Florian Franz |author2=Nadja Schwörer |author3=Verena Angerer |author4=Bjoern Moosmann |author5=Volker Auwärter | journal=Toxichem Krimtech | date=2015 | volume=82 | pages=192}}</ref><ref>{{cite journal|first1=Andrej|last1=Grigoryev|first2=Pierce|last2=Kavanagh|first3=Alexandr|last3=Pechnikov|title=Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate|url=http://link.springer.com/article/10.1007/s11419-016-0319-8|journal=Forensic Toxicology|date=23 April 2016|pages=316–328|volume=34|issue=2|doi=10.1007/s11419-016-0319-8}}</ref>
On October 29, 2014 the state of Louisiana emergency scheduled MDMB-CHMICA into [[List of Schedule I drugs (US)|Schedule I]].<ref>{{cite web | url=http://dhh.louisiana.gov/index.cfm/newsroom/detail/3161 | title=Gov. Jindal and State Officials Ban New Synthetic Marijuana Compound | accessdate=29 June 2015}}</ref>


== Side Effects ==
MDMB-CHMICA falls into Anlage II of the Neue Psychoaktive Substanzen Gesetz (NPSG) and is therefore illegal in Austria.<ref>{{cite web | url=http://www.praevention.at/news/index.php/action.view/entity.detail/key.1301/nav.6/view.29/level.2/ | title=Räuchermischung "Bonzai": Was steckt dahinter? | publisher=Initiative Suchtprävention | date=17 December 2014 | language=German | accessdate=29 June 2015}}</ref>
71 serious adverse events, including 42 acute intoxications and 29 deaths (Germany (5), Hungary (3), Poland (1), Sweden (9), United Kingdom (10), Norway (1)) which occured in 9 European countries between 2014 and 2016 have been associated with MDMB-CHMICA.<ref name="EMCDDA"/><ref>{{cite web | url=http://www.bbc.com/news/uk-england-derbyshire-32477643 | title=Derby legal high confusion prompts police warning | publisher=BBC | date=29 April 2015 | accessdate=29 June 2015}}</ref><ref>{{cite web | url=http://www.talkingdrugs.org/drug-alert-dangerous-synthetic-cannabinoid-mmb-chminaca-causing-hospitalizations-deaths-in-europe | title=Drug Alert: Dangerous Synthetic Cannabinoid MMB-CHMINACA Causing Hospitalizations, Deaths in Europe | publisher=TalkingDrugs | date=2 July 2015 | accessdate=2 July 2015}}</ref><ref>{{cite journal | url=http://jat.oxfordjournals.org/content/40/1/86 | title=Sudden Cardiac Death Following Use of the Synthetic Cannabinoid MDMB-CHMICA |author1=Andreas Austgulen Westin |author2=Joachim Frost |author3=Wenche Rødseth Brede |author4=Per Ole M. Gundersen |author5=Steinar Einvik |author6=Harald Aarset |author7=Lars Slørdal | journal=Journal of Analytical Toxicology | date=February 2016 | volume=40 | issue=1 | pages=86–87 | doi=10.1093/jat/bkv110 | pmid=26353925}}</ref><ref>{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0379073816300469 | title=Fatal intoxication with synthetic cannabinoid MDMB-CHMICA | author=Piotr Adamowicz | journal=Forensic Science International | date=April 2016 | volume=261 | pages=e5–e10 | doi=10.1016/j.forsciint.2016.02.024 | pmid=26934903}}</ref>


Side effects such as unconsciousness or coma, hyperemesis, nausea, seizures, convulsions, tachycardia, bradycardia, mydriasis, syncope, spontaneous urinating and defecating, shortness of breath, somnolence, respiratory acidosis, metabolic acidosis, collapse, lower limbs paralysis, chest pain, aggression and severe disturbance of behaviour were reported.<ref name="EMCDDA"/><ref>{{cite journal | author1=Alice Seywright | url=http://www.tandfonline.com/doi/abs/10.1080/15563650.2016.1186805 | title=Analysis and clinical findings of cases positive for the novel synthetic cannabinoid receptor agonist MDMB-CHMICA | date=May 2016 | author2=Hazel J. Torrance | author3=Fiona M. Wylie | author4=Denise A. McKeown | author5=David J. Lowe | author6=Richard Stevenson | journal=Clinical Toxicology | pages=1–6 | doi=10.1080/15563650.2016.1186805 | pmid=27213960}}</ref><ref>{{cite journal|first1=Simon L.|last1=Hill|first2=Javad|last2=Najafi|first3=Michael|last3=Dunn|first4=Paul|last4=Acheampong|title=Clinical toxicity following analytically confirmed use of the synthetic cannabinoid receptor agonist MDMB-CHMICA. A report from the Identification Of Novel psychoActive substances (IONA) study|url=http://dx.doi.org/10.1080/15563650.2016.1190980|journal=Clinical Toxicology|date=2 June 2016|pages=1–6|volume=0|issue=0|doi=10.1080/15563650.2016.1190980|pmid=27251903|first5=Ashraf|last5=Kamour|first6=Johann|last6=Grundlingh|first7=Peter G.|last7=Blain|first8=Simon H. L.|last8=Thomas}}</ref><ref>{{cite journal|first1=Robert J.|last1=Tait|first2=David|last2=Caldicott|first3=David|last3=Mountain|first4=Simon L.|last4=Hill|title=A systematic review of adverse events arising from the use of synthetic cannabinoids and their associated treatment|url=http://www.tandfonline.com/doi/abs/10.3109/15563650.2015.1110590|journal=Clinical Toxicology|date=2 January 2016|pages=1–13|volume=54|issue=1|doi=10.3109/15563650.2015.1110590|pmid=26567470|first5=Simon|last5=Lenton}}</ref>
MDMB-CHMICA is an [[Drugs controlled by the German Betäubungsmittelgesetz|Anlage II]] controlled drug in Germany.<ref>{{cite web | url=http://www.bfarm.de/DE/Bundesopiumstelle/Betaeubungsmittel/Sachverst/Sitzungen/Tagesordnung_44.html?nn=3495700 | title=44. Sitzung des Sachverständigenausschusses | publisher=Bundesinstitut für Arzneimittel und Medizinprodukte (BfArM) | language=German | date=17 April 2015 | accessdate=29 June 2015}}</ref>


== Legal status ==
Sweden's public health agency suggested classifying MDMB-CHMICA as hazardous substance on November 10, 2014.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassade som hälsofarlig vara | publisher=Folkhälsomyndigheten | language=Swedish | accessdate=29 June 2015}}</ref>
MDMB-CHMICA is illegal in Austria, Canada, China,<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref> Croatia, Denmark, Estonia, Finland, Germany, Greece, Hungary, Latvia, Lithuania, Louisiana,<ref>{{cite web | url=http://dhh.louisiana.gov/index.cfm/newsroom/detail/3161 | title=Gov. Jindal and State Officials Ban New Synthetic Marijuana Compound | accessdate=29 June 2015}}</ref> Luxembourg, Norway, Poland, Turkey, Sweden & Switzerland.<ref name="EMCDDA"/>

As of October 2015 MDMB-CHMICA is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>

MDMB-CHMICA is illegal in Switzerland as of December 2015.<ref>{{cite web | url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html | title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien | publisher=Der Bundesrat | language=German}}</ref>

It is illegal in Germany since 21.11.2015.<ref>{{Cite web|url=http://blog.beck.de/2015/11/23/30-btm-ndvo-in-kraft-getreten-6-neue-stoffe-wurden-ins-btmg-aufgenommen-0|title=30. BtMÄndVO in Kraft getreten: 6 neue Stoffe wurden ins BtMG aufgenommen {{!}} beck-community|website=blog.beck.de|access-date=2016-06-23}}</ref>


==See also==
==See also==
{{div col|colwidth=30em}}
{{div col|colwidth=30em}}
* [[5F-AB-PINACA]]
* [[5F-ADB]]
* [[5F-AMB]]
* [[5F-APINACA]]
* [[AB-FUBINACA]]
* [[AB-CHFUPYCA]]
* [[AB-CHMINACA]]
* [[AB-CHMINACA]]
* [[AB-PINACA]]
* [[ADB-CHMINACA]]
* [[ADB-CHMINACA]]
* [[ADB-FUBINACA]]
* [[AMB-CHMINACA]]
* [[ADB-PINACA]]
* [[ADBICA]]
* [[APICA]]
* [[APINACA]]
* [[MDMB-CHMINACA]]
* [[MDMB-CHMINACA]]
* [[MDMB-FUBINACA]]
* [[MDMB-FUBINACA]]

Revision as of 03:02, 10 July 2016

MDMB-CHMICA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • Illegal in Austria, China, Croatia, Denmark, Estonia, Finland, Greece, Hungary, Latvia, Lithuania, Louisiana, Luxembourg, Norway, Poland, Turkey, Sweden & Switzerland[1]
Identifiers
  • methyl (2S)-2-{[1-(cyclohexylmethyl)-1H-indol-3-yl]formamido}-3,3-dimethylbutanoate
CAS Number
ChemSpider
Chemical and physical data
FormulaC23H32N2O3
Molar mass384.520 g·mol−1
3D model (JSmol)
  • COC(=O)[C@@H](NC(=O)c1cn(CC2CCCCC2)c3ccccc13)C(C)(C)C
  • InChI=1S/C23H32N2O3/c1-23(2,3)20(22(27)28-4)24-21(26)18-15-25(14-16-10-6-5-7-11-16)19-13-9-8-12-17(18)19/h8-9,12-13,15-16,20H,5-7,10-11,14H2,1-4H3,(H,24,26)/t20-/m1/s1
  • Key:SRJKCVHWIDFUBO-HXUWFJFHSA-N

MDMB-CHMICA (also incorrectly known as MMB-CHMINACA) is an indole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug.[1][2][3] While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue of MDMB-CHMINACA) has been identified on the designer drug market in 2015 as AMB-CHMINACA.[4]

Seizures

Over 3600 MDMB-CHMICA seizures between 2014 and 2016 in 19 member states of the European Union have been reported to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA),[1] including a 40 kg seizure in Luxembourg in December 2014.[5]

Chemistry

Several commercial samples of MDMB-CHMICA were found to exclusively contain the (S)-enantiomer based on vibrational and electronic circular dichroism spectroscopy and X-ray crystallography.[6] An (S)-configuration for the tert-leucinate group is unsurprising since MDMB-CHMICA is likely synthesized from the abundant and inexpensive "L" form of the appropriate tert-leucinate reactant.

Pharmacology

MDMB-CHMICA acts as a highly potent full agonist of the CB1 receptor with an efficacy of 94% and an EC50 value of 0.14 nM, which is approximately 8 times lower than the EC50 of JWH-018 (1.13 nM) and twofold lower than AB-CHMINACA (0.27 nM).[1][7]

Metabolism

MDMB-CHMICAs main metabolic reactions comprise mono-hydroxylations and hydrolysis of the carboxylic ester function. In total, 31 metabolites could be identified in vivo.[8][9]

Side Effects

71 serious adverse events, including 42 acute intoxications and 29 deaths (Germany (5), Hungary (3), Poland (1), Sweden (9), United Kingdom (10), Norway (1)) which occured in 9 European countries between 2014 and 2016 have been associated with MDMB-CHMICA.[1][10][11][12][13]

Side effects such as unconsciousness or coma, hyperemesis, nausea, seizures, convulsions, tachycardia, bradycardia, mydriasis, syncope, spontaneous urinating and defecating, shortness of breath, somnolence, respiratory acidosis, metabolic acidosis, collapse, lower limbs paralysis, chest pain, aggression and severe disturbance of behaviour were reported.[1][14][15][16]

Legal status

MDMB-CHMICA is illegal in Austria, Canada, China,[17] Croatia, Denmark, Estonia, Finland, Germany, Greece, Hungary, Latvia, Lithuania, Louisiana,[18] Luxembourg, Norway, Poland, Turkey, Sweden & Switzerland.[1]

See also

References

  1. ^ a b c d e f g "EMCDDA–Europol Joint Report on MDMB-CHMICA" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). July 2016. doi:10.2810/08132. ISBN 978-92-9168-925-5.
  2. ^ "MDMB-CHMICA". Cayman Chemical. Retrieved 29 June 2015.
  3. ^ "MDMB-CHMICA". Southern Association of Forensic Scientists. Retrieved 29 June 2015.
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