Meclonazepam

Chemical compound From Wikipedia, the free encyclopedia

Meclonazepam[1] ((S)-3-methylclonazepam) is a benzodiazepine derivative similar in structure to clonazepam. It was first discovered by a team at Hoffmann-La Roche in the 1970s.[2] It has sedative and anxiolytic actions like those of other benzodiazepines,[3] and also has anti-parasitic effects against the parasitic worm Schistosoma mansoni.[4]

ATC code
  • none
Legal status
Quick facts Clinical data, ATC code ...
Meclonazepam
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (3S)-5-(2-chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H12ClN3O3
Molar mass329.74 g·mol−1
3D model (JSmol)
  • O=N(C1=CC2=C(NC([C@H](C)N=C2C3=CC=CC=C3)=O)C=C1)=O
  • InChI=1S/C16H12ClN3O3/c1-9-16(21)19-14-7-6-10(20(22)23)8-12(14)15(18-9)11-4-2-3-5-13(11)17/h2-9H,1H3,(H,19,21)/t9-/m0/s1 checkY
  • Key:LMUVYJCAFWGNSY-VIFPVBQESA-N checkY
 ☒NcheckY (what is this?)  (verify)
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Meclonazepam was never used as medicine and instead appeared online as a designer drug.[5][6][7][8]

Pharmacology

Its sedative and anxiolytic abilities are attributed to the same mechanism used by other benzodiazepine drugs: modulation of the GABAA receptor in the brain. This psychoactive activity makes it useful for recreational use.[7] The sedating side effect would also make it unsuitable for routine use as an antiparasitical.[9]

Schistosomal parasites do not have an ortholog of the GABAA receptor. Instead, meclonazepam seems to cause a rapid calcium influx, leading to muscle contraction and tegument damage. In 2023, meclonazepam is shown to activate a calcium-permeable schistosome TRP (transient receptor potential), making this TRP a very likely candidate for its parasite receptor.[9]

Some work has been done to produce two meclonazepam derivatives that show less sedation and more anti-parasite activity in mice. They seem to do this by crossing the blood-brain barrier less readily.[9]

United Kingdom

In the UK, meclonazepam has been classified as a Class C drug by the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other designer benzodiazepine drugs.[10]

See also

References

Further reading

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