Phenazolam

Phenazolam
Clinical data
Trade names	(none, designer drug)
Legal status
Legal status	CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; Illegal in Serbia and Italy;
Identifiers
	IUPAC name 8-bromo-6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine;
CAS Number	87213-50-1 ;
PubChem CID	1032830;
ChemSpider	887985;
UNII	2AVB9ZZ4ZS;
ChEMBL	ChEMBL1451229;
CompTox Dashboard (EPA)	DTXSID10236191;
Chemical and physical data
Formula	C17H12BrClN4
Molar mass	387.67 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=NN=C2N1C3=C(C=C(C=C3)Br)C(=NC2)C4=CC=CC=C4Cl;
	InChI InChI=1S/C17H12BrClN4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3; Key:BUTCFAZTKZDYCN-UHFFFAOYSA-N;

Phenazolam, (Clobromazolam, DM-II-90, BRN 4550445) is a benzodiazepine derivative which acts as a potent sedative and hypnotic drug. It was first invented in the early 1980s,^[1] but was never developed for medical use. It has been sold over the internet as a designer drug, first being identified in seized samples by a laboratory in Sweden in March 2016.^[2]^[3]

Legality

Clobromazolam was made illegal in Serbia in May 2019,^[4] and in Italy in March 2020.^[5]

References

^ Polívka Z, Holubek J, Metyš J, Šedivŷ Z, Protiva M (1983). "Potential hypnotics and anxiolytics: 8-Chloro-6-(2-chlorophenyl)-1-[4-(2-methoxyethyl) piperazino]-methyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine and related compounds". Collection of Czechoslovak Chemical Communications. 48 (12): 3433–43. doi:10.1135/cccc19833433.
^ "Novel Benzodiazepines. A review of the evidence of use and harms of Novel Benzodiazepines" (PDF). Advisory Council on the Misuse of Drugs. April 2020.
^ Wagmann L, Manier SK, Felske C, Gampfer TM, Richter MJ, Eckstein N, Meyer MR (October 2020). "Flubromazolam-Derived Designer Benzodiazepines: Toxicokinetics and Analytical Toxicology of Clobromazolam and Bromazolam". Journal of Analytical Toxicology. 45 (9): 1014–1027. doi:10.1093/jat/bkaa161. PMID 33048135.
^ ""Службени гласник РС", број 38 од 31. маја 2019" [Rulebook on determining the List of psychoactive controlled substances: 38 / 2019-121] (in Serbian). Serbian Ministry of Health.
^ "Legislazione - MINISTERO SALUTE - Decreto ministeriale" [Legislation - MINISTRY HEALTH - Ministerial decree] (in Italian). 13 March 2020.

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[1] Polívka Z, Holubek J, Metyš J, Šedivŷ Z, Protiva M (1983). "Potential hypnotics and anxiolytics: 8-Chloro-6-(2-chlorophenyl)-1-[4-(2-methoxyethyl) piperazino]-methyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine and related compounds". Collection of Czechoslovak Chemical Communications. 48 (12): 3433–43. doi:10.1135/cccc19833433.

[2] "Novel Benzodiazepines. A review of the evidence of use and harms of Novel Benzodiazepines" (PDF). Advisory Council on the Misuse of Drugs. April 2020.

[pmid33048135-3] Wagmann L, Manier SK, Felske C, Gampfer TM, Richter MJ, Eckstein N, Meyer MR (October 2020). "Flubromazolam-Derived Designer Benzodiazepines: Toxicokinetics and Analytical Toxicology of Clobromazolam and Bromazolam". Journal of Analytical Toxicology. 45 (9): 1014–1027. doi:10.1093/jat/bkaa161. PMID 33048135.

[4] ""Службени гласник РС", број 38 од 31. маја 2019" [Rulebook on determining the List of psychoactive controlled substances: 38 / 2019-121] (in Serbian). Serbian Ministry of Health.

[5] "Legislazione - MINISTERO SALUTE - Decreto ministeriale" [Legislation - MINISTRY HEALTH - Ministerial decree] (in Italian). 13 March 2020.

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v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite of Rilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (not GABA_A receptor ligands)

Legality

See also

References