Nitemazepam

Nitemazepam
Legal status
Legal status	CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 7-nitro-3-hydroxy-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one;
CAS Number	40762-03-6;
PubChem CID	12362353;
ChemSpider	64854354;
UNII	DFJ6M9363O;
Chemical and physical data
Formula	C16H13N3O4
Molar mass	311.297 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=[N+](O)c1ccc2c(c1)C(=NC(O)C(=O)N2C)c3ccccc3;
	InChI InChI=1S/C16H13N3O4/c1-18-13-8-7-11(19(22)23)9-12(13)14(17-15(20)16(18)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3; Key:QRWVNMAJJIQCEG-UHFFFAOYSA-N;

Nitemazepam (or 3-hydroxynimetazepam) is a benzodiazepine derivative which was first synthesised in the 1970s but was never marketed. It is the 7-nitro instead of 7-chloro analogue of temazepam, and also the 3-hydroxy derivative of nimetazepam, and an active metabolite. It has in more recent years been sold as a designer drug, first being definitively identified in Europe in 2017. It is metabolized to 7-aminonitemazepam, nimetazepam, 3-hydroxynitemazepam, temazepam, and nimetazepam glucuronide.^[1]^[2]

References

^ Zawilska JB, Wojcieszak J (July 2019). "An expanding world of new psychoactive substances-designer benzodiazepines". Neurotoxicology. 73: 8–16. doi:10.1016/j.neuro.2019.02.015. PMID 30802466. S2CID 73461430.
^ Moosmann B, Auwärter V (2018). "Designer Benzodiazepines: Another Class of New Psychoactive Substances.". In Maurer H, Brandt S (eds.). New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 383–410. doi:10.1007/164_2018_154. ISBN 978-3-030-10560-0. PMID 30367253.

[pmid30802466-1] Zawilska JB, Wojcieszak J (July 2019). "An expanding world of new psychoactive substances-designer benzodiazepines". Neurotoxicology. 73: 8–16. doi:10.1016/j.neuro.2019.02.015. PMID 30802466. S2CID 73461430.

[2] Moosmann B, Auwärter V (2018). "Designer Benzodiazepines: Another Class of New Psychoactive Substances.". In Maurer H, Brandt S (eds.). New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 383–410. doi:10.1007/164_2018_154. ISBN 978-3-030-10560-0. PMID 30367253.

[1]

[2]

Legal status

Legal status	CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 7-nitro-3-hydroxy-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one
CAS Number	40762-03-6
PubChem CID	12362353
ChemSpider	64854354
UNII	DFJ6M9363O
Chemical and physical data
Formula	C₁₆H₁₃N₃O₄
Molar mass	311.297 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=[N+](O)c1ccc2c(c1)C(=NC(O)C(=O)N2C)c3ccccc3
InChI InChI=1S/C16H13N3O4/c1-18-13-8-7-11(19(22)23)9-12(13)14(17-15(20)16(18)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3 Key:QRWVNMAJJIQCEG-UHFFFAOYSA-N