104255-56-3

Basic information

• Product Name: 4H-1,4-Benzoxazin-4-amine,2,3-dihydro-(9CI)
• Synonyms: 4H-1,4-Benzoxazin-4-amine,2,3-dihydro-(9CI);2H-benzo[b][1,4]oxazin-4(3H)-amine;4H-1,4-Benzoxazin-4-aMine, 2,3-dihydro-;2,3-Dihydro-4H-1,4-benzoxazin-4-amine;3,4-Dihydro-2H-1,4-benzoxazin-4-aMine
• CAS NO: 104255-56-3
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.18
• Product Categories: AMINEPRIMARY
• Mol File: 104255-56-3.mol

Chemical Properties

• Boiling Point: 277℃
• Flash Point: 121℃
• Appearance: /
• Density: 1.192
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4H-1,4-Benzoxazin-4-amine,2,3-dihydro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1,4-Benzoxazin-4-amine,2,3-dihydro-(9CI)(104255-56-3)
• EPA Substance Registry System: 4H-1,4-Benzoxazin-4-amine,2,3-dihydro-(9CI)(104255-56-3)

Safety Data

• Hazardous Substances Data: 104255-56-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H10N2O/c9-10-5-6-11-8-4-2-1-3-7(8)10/h1-4H,5-6,9H2

Upstream product

• 98491-38-4 3,4-dihydro-2H-benzo[b][1,4]oxazine hydrochloride 
• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 5735-53-5 1,4-benzoxazine 
• 63169-10-8 4-nitroso-3,4-dihydro-2H-benzo[b][1,4]oxazine 

Downstream Products

• 1576240-08-8 (6bS, 11aS)-4-(1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indol-9-yl)-1-(4-fluorophenyl)-1-butanone 

Relevant articles and documents

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Design and synthesis of a metabolically stable and potent antitussive agent, a novel δ opioid receptor antagonist, TRK-851

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Development of high-affinity 5-HT3 receptor antagonists. Structure- affinity relationships of novel 1,7-annelated indole derivatives. 1

On the basis of the structures of ondansetron and GR 65,630, its ring- opened C-linked methylimidazole analogue, novel 1,7-annelated indole derivatives were synthesized as potential 5-HT3 antagonists. Receptor binding studies show that all compounds display a high affinity for the 5- HT3 receptors. In both series annelation results in compounds being 7 and 4 times more potent than the references ondansetron and GR 65,630, respectively. Similar to ondansetron, the 1,7-annelated indoles show little stereoselectivity. The (-)-isomers are only slightly more potent than the (+)-isomers. The receptor binding profile of l-10-[(2-methyl-1H-imidazol-1- yl)methyl]-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-11-one hydrochloride (24b) (INN cilansetron) shows that the compound displays, besides a high affinity for 5-HT3 receptors (K(i) = 0.19 nM), a weak affinity for σ-receptors (K(i) = 340 nM), muscarine M1 receptors (K(i) = 910 nM), and 5-HT4 receptors (K(i) = 960 nM) and no affinity (K(i) ≥ 5000 nM) for all the other receptor types tested (n = 37). The new compounds fit the proposed necessary chemical template for binding: a heteroaromatic ring system, a coplanar carbonyl group, and a nitrogen center at well-defined distances. The enhanced potency of the annelated 1,7-indole derivatives indicates that the extra ring provides a favorable hydrophobic area for interaction with the 5-HT3 receptor site. In vivo cilansetron is more potent and induces less central side effects than ondansetron. At present cilansetron is in clinical trials.