Meclonazepam information

Meclonazepam
Clinical data
ATC code	none;
Legal status
Legal status	CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name (3S)-5-(2-chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one;
CAS Number	58662-84-3 ;
PubChem CID	3033985;
ChemSpider	2298544 ;
UNII	RN43209SMA;
ChEMBL	ChEMBL351821 ;
CompTox Dashboard (EPA)	DTXSID10207366 ;
Chemical and physical data
Formula	C16H12ClN3O3
Molar mass	329.74 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=N(C1=CC2=C(NC([C@H](C)N=C2C3=CC=CC=C3)=O)C=C1)=O;
	InChI 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 ; Key:LMUVYJCAFWGNSY-VIFPVBQESA-N ;
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Meclonazepam^[1] ((S)-3-methylclonazepam) was discovered by a team at Hoffmann-La Roche in the 1970s and is a drug which is a benzodiazepine derivative similar in structure to clonazepam.^[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]

Meclonazepam was never used as medicine and instead appeared online as a designer drug.^[5]^[6]^[7]^[8]

^ US 4031078, Szente A, "Benzodiazepine derivatives", issued 21 June 1977, assigned to Hoffmann La Roche Inc.
^ The Lundbeck Institute. "Meclonazepam". Psychotropics. Lundbeck.
^ Ansseau M, Doumont A, Thiry D, von Frenckell R, Collard J (1985). "Initial study of methylclonazepam in generalized anxiety disorder. Evidence for greater power in the cross-over design" (PDF). Psychopharmacology. 87 (2): 130–135. doi:10.1007/bf00431795. PMID 3931136. S2CID 9776700.
^ O'Boyle C, Lambe R, Darragh A (1985). "Central effects in man of the novel schistosomicidal benzodiazepine meclonazepam". European Journal of Clinical Pharmacology. 29 (1): 105–108. doi:10.1007/bf00547377. PMID 4054198. S2CID 1150292.
^ Meyer MR, Bergstrand MP, Helander A, Beck O (May 2016). "Identification of main human urinary metabolites of the designer nitrobenzodiazepines clonazolam, meclonazepam, and nifoxipam by nano-liquid chromatography-high-resolution mass spectrometry for drug testing purposes". Analytical and Bioanalytical Chemistry. 408 (13): 3571–3591. doi:10.1007/s00216-016-9439-6. PMID 27071765. S2CID 25831532.
^ Pettersson Bergstrand M, Helander A, Hansson T, Beck O (April 2017). "Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays". Drug Testing and Analysis. 9 (4): 640–645. doi:10.1002/dta.2003. PMID 27366870.
^ Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D_7.4 , pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances". Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID 29582576.
^ Manchester KR, Waters L, Haider S, Maskell PD (July 2022). "The blood-to-plasma ratio and predicted GABA_A-binding affinity of designer benzodiazepines". Forensic Toxicology. 40 (2): 349–356. doi:10.1007/s11419-022-00616-y. PMC 9715504. PMID 36454409.

[1] US 4031078, Szente A, "Benzodiazepine derivatives", issued 21 June 1977, assigned to Hoffmann La Roche Inc.

[2] The Lundbeck Institute. "Meclonazepam". Psychotropics. Lundbeck.

[3] Ansseau M, Doumont A, Thiry D, von Frenckell R, Collard J (1985). "Initial study of methylclonazepam in generalized anxiety disorder. Evidence for greater power in the cross-over design" (PDF). Psychopharmacology. 87 (2): 130–135. doi:10.1007/bf00431795. PMID 3931136. S2CID 9776700.

[4] O'Boyle C, Lambe R, Darragh A (1985). "Central effects in man of the novel schistosomicidal benzodiazepine meclonazepam". European Journal of Clinical Pharmacology. 29 (1): 105–108. doi:10.1007/bf00547377. PMID 4054198. S2CID 1150292.

[5] Meyer MR, Bergstrand MP, Helander A, Beck O (May 2016). "Identification of main human urinary metabolites of the designer nitrobenzodiazepines clonazolam, meclonazepam, and nifoxipam by nano-liquid chromatography-high-resolution mass spectrometry for drug testing purposes". Analytical and Bioanalytical Chemistry. 408 (13): 3571–3591. doi:10.1007/s00216-016-9439-6. PMID 27071765. S2CID 25831532.

[6] Pettersson Bergstrand M, Helander A, Hansson T, Beck O (April 2017). "Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays". Drug Testing and Analysis. 9 (4): 640–645. doi:10.1002/dta.2003. PMID 27366870.

[7] Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D_7.4 , pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances". Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID 29582576.

[8] Manchester KR, Waters L, Haider S, Maskell PD (July 2022). "The blood-to-plasma ratio and predicted GABA_A-binding affinity of designer benzodiazepines". Forensic Toxicology. 40 (2): 349–356. doi:10.1007/s11419-022-00616-y. PMC 9715504. PMID 36454409.

Meclonazepam information

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Clinical data

ATC code	none
Legal status
Legal status	CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name (3S)-5-(2-chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number	58662-84-3^N
PubChem CID	3033985
ChemSpider	2298544^Y
UNII	RN43209SMA
ChEMBL	ChEMBL351821^N
CompTox Dashboard (EPA)	DTXSID10207366
Chemical and physical data
Formula	C₁₆H₁₂ClN₃O₃
Molar mass	329.74 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=N(C1=CC2=C(NC([C@H](C)N=C2C3=CC=CC=C3)=O)C=C1)=O
InChI 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^Y Key:LMUVYJCAFWGNSY-VIFPVBQESA-N^Y
^NY (what is this?) (verify)