Triazolobenzodiazepime
Bromazolam Legal status
8-bromo-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine
CAS Number PubChem CID ChemSpider UNII ChEMBL Formula C 17 H 13 Br N 4 Molar mass 353.223 g·mol−1 3D model (JSmol )
Brc1cc2C(=NCc3nnc(C)n3c2cc1)c4ccccc4
InChI=1S/C17H13BrN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
Key:KCEIOBKDDQAYCM-UHFFFAOYSA-N
Bromazolam (XLI-268 ) is a triazolobenzodiazepine (TBZD) which was first synthesised in 1976, but was never marketed.[1] It has subsequently been sold as a designer drug , first being definitively identified by the EMCDDA in Sweden in 2016.[2] It is the bromo instead of chloro analogue of alprazolam and has similar sedative and anxiolytic effects to it and other benzodiazepines .[3] [4] Bromazolam is a non subtype selective agonist at the benzodiazepine site of GABAA receptors , with a binding affinity of 2.81nM at the α1 subtype, 0.69nM at α2 and 0.62nM at α5 .[5]
See also [ ]
Clobromazolam
Flualprazolam
Flubromazolam
Pyrazolam
Triazolam
References [ ]
^ Manchester KR, Lomas EC, Waters L, Dempsey FC, Maskell PD (January 2018). "The emergence of new psychoactive substance (NPS) benzodiazepines: A review" . Drug Testing and Analysis . 10 (1): 37–53. doi :10.1002/dta.2211 . PMID 28471096 .
^ "Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA. EMCDDA" (PDF) . European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) and European Union Agency for Law Enforcement Cooperation (Europol). 2017.
^ Waters L, Manchester KR, Maskell PD, Haegeman C, Haider S (May 2018). "The use of a quantitative structure-activity relationship (QSAR) model to predict GABA-A receptor binding of newly emerging benzodiazepines" (PDF) . Science & Justice . 58 (3): 219–225. doi :10.1016/j.scijus.2017.12.004 . PMID 29685303 .
^ 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 .
^ Clayton T, Poe MM, Rallapalli S, Biawat P, Savić MM, Rowlett JK, Gallos G, Emala CW, Kaczorowski CC, Stafford DC, Arnold LA, Cook JM (2015). "A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model" . International Journal of Medicinal Chemistry . 2015 : 430248. doi :10.1155/2015/430248 . PMC 4657098 . PMID 26682068 .
Benzodiazepines
1,4-Benzodiazepines 1,5-Benzodiazepines
Arfendazam
Clobazam
CP-1414S
Lofendazam
Triflubazam
2,3-Benzodiazepines*
Girisopam
GYKI-52466
GYKI-52895
Nerisopam
Talampanel
Tofisopam
Triazolobenzodiazepines Imidazobenzodiazepines
Bretazenil
Climazolam
EVT-201
FG-8205
Flumazenil
GL-II-73
Imidazenil
123 I-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 Thienotriazolodiazepines Thienobenzodiazepines *Pyridodiazepines Pyridotriazolodiazepines Pyrazolodiazepines Pyrrolodiazepines Tetrahydroisoquinobenzodiazepines Pyrrolobenzodiazepines *Benzodiazepine prodrugs * atypical activity profile (not GABAA receptor ligands)
Hypnotics /sedatives (N05C )
GABAA
Alcohols Barbiturates Benzodiazepines
Brotizolam
Cinolazepam
Climazolam
Clonazepam
Doxefazepam
Estazolam
Flunitrazepam
Flurazepam
Flutoprazepam
Lorazepam
Loprazolam
Lormetazepam
Midazolam
Nimetazepam
Nitrazepam
Phenazepam
Quazepam
Temazepam
Triazolam
Carbamates Imidazoles Monoureides Neuroactive steroids Nonbenzodiazepines Phenols Piperidinediones Quinazolinones Others
GABAB
1,4-Butanediol
4-Fluorophenibut
Aceburic acid
Baclofen
GABOB
GHB (sodium oxybate )
GBL
GVL
Phenibut
Tolibut
H1
Antihistamines
Captodiame
Cyproheptadine
Diphenhydramine
Doxylamine
Hydroxyzine
Methapyrilene
Perlapine
Pheniramine
Promethazine
Propiomazine
Antidepressants
Serotonin antagonists and reuptake inhibitors
Etoperidone
Nefazodone
Trazodone
Tricyclic antidepressants
Amitriptyline
Doxepin
Trimipramine , etc.
Tetracyclic antidepressants
Antipsychotics
Typical antipsychotics
Chlorpromazine
Thioridazine , etc.
Atypical antipsychotics
α2 -Adrenergic
Clonidine
Detomidine
Dexmedetomidine
Lofexidine
Medetomidine
Romifidine
Tizanidine
Xylazine
5-HT2A
Antidepressants
Trazodone
Tricyclic antidepressants
Amitriptyline
Doxepin
Trimipramine , etc.
Tetracyclic antidepressants
Antipsychotics
Typical antipsychotics
Chlorpromazine
Thioridazine , etc.
Atypical antipsychotics
Others
Melatonin Orexin α2 δ VDCC
Gabapentin
Gabapentin enacarbil
Mirogabalin
Phenibut
Pregabalin
Others
Cannabidiol
Diethylpropanediol
Evoxine
Fenadiazole
Guaifenesin -related muscle relaxants
Chlorphenesin
Mephenesin
Mephenoxalone
Metaxalone
Methocarbamol
Midaflur
Opioids (e.g., morphine )
Passion flower
Scopolamine
Trazodone
UMB68
Valnoctamide
GABA A receptor positive modulatorsAlcohols
Butanol
Chloralodol
Chlorobutanol (cloretone)
Ethanol (alcohol) (alcoholic drink )
Ethchlorvynol
Isobutanol
Isopropanol
Menthol
Methanol
Methylpentynol
Pentanol
Petrichloral
Propanol
tert -Butanol (2M2P)
tert -Pentanol (2M2B)
Tribromoethanol
Trichloroethanol
Triclofos
Trifluoroethanol
Barbiturates Benzodiazepines Carbamates Flavonoids
Ampelopsin (dihydromyricetin)
Apigenin
Baicalein
Baicalin
Catechin
EGC
EGCG
Hispidulin
Luteolin
Skullcap constituents (e.g., baicalin )
Wogonin
Imidazoles Kava constituents
Desmethoxyyangonin
Kavain
Methysticin
Yangonin
Monoureides Neuroactive steroids Nonbenzodiazepines Phenols
Fospropofol
Propofol
Thymol
Piperidinediones Pyrazolopyridines Quinazolinones Volatiles /gases
Acetone
Acetophenone
Acetylglycinamide chloral hydrate
Aliflurane
Benzene
Butane
Butylene
Centalun
Chloral
Chloral betaine
Chloral hydrate
Chloroform
Cryofluorane
Desflurane
Dichloralphenazone
Dichloromethane
Diethyl ether
Enflurane
Ethyl chloride
Ethylene
Fluroxene
Gasoline
Halopropane
Halothane
Isoflurane
Kerosine
Methoxyflurane
Methoxypropane
Nitric oxide
Nitrogen
Nitrous oxide
Norflurane
Paraldehyde
Propane
Propylene
Roflurane
Sevoflurane
Synthane
Teflurane
Toluene
Trichloroethane (methyl chloroform)
Trichloroethylene
Vinyl ether
Others/unsorted
3-Hydroxybutanal
Avermectins (e.g., ivermectin )
Bromide compounds (e.g., lithium bromide , potassium bromide , sodium bromide )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
DEABL
Dihydroergolines (e.g., dihydroergocryptine , , dihydroergotamine , ergoloid (dihydroergotoxine) )
Efavirenz
Etazepine
Etifoxine
Fenamates (e.g., flufenamic acid , mefenamic acid , niflumic acid , tolfenamic acid )
Fluoxetine
Flupirtine
Hopantenic acid
Lanthanum
Lavender oil
Lignans (e.g., 4-O-methylhonokiol , honokiol , magnolol , obovatol )
Loreclezole
Menthyl isovalerate (validolum)
Monastrol
Niacin
Niacinamide
Org 25,435
Phenytoin
Propanidid
Retigabine (ezogabine)
Safranal
Seproxetine
Stiripentol
(e.g., sulfonmethane (sulfonal) , tetronal , trional )
Terpenoids (e.g., borneol )
Topiramate
Valerian constituents (e.g., isovaleric acid , isovaleramide , valerenic acid , )
Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators