Amg-9810
Basic information
- CAS
545395-94-6- Standard SMILES
CC(C)(C)c1ccc(/C=C/C(=O)Nc2ccc3c(c2)OCCO3)cc1- InChIKey
GZTFUVZVLYUPRG-IZZDOVSWSA-N- Molecular formula
- C21H23NO3
- Average molar mass
- 337.4 g/mol
- Monoisotopic mass
- 337.1677936
Overview
3-(4-tert-butylphenyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-propenamide is a secondary carboxamide and a member of cinnamamides.
Names & identifiers
- Preferred name
- Amg-9810
- IUPAC
- (E)-3-(4-tert-butylphenyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-enamide
- English name
- AMG 9810
- Molecular formula
- C21H23NO3
- Molecular weight
- 337.41
Names & synonyms
545395-94-6AMG9810AMG 9810AMG-9810182HIJ2D7F2E-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(1,1-dimethylethyl)phenyl]-2-Propenamide3-(4-tert-butylphenyl)-N-(2,3-dihydro-1,4-benzodioxin-7-yl)prop-2-enamide(2E)-N-(2H,3H-BENZO(3,4-E)-1,4-DIOXAN-6-YL)-3-(4-(TERT-BUTYL)PHENYL)PROP-2-ENAMIDE2-PROPENAMIDE, N-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)-3-(4-(1,1-DIMETHYLETHYL)PHENYL)-, (2E)-2E-N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(4-(1,1-dimethylethyl)phenyl)-2-propenamide2-Propenamide, N-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[4-(1,1-dimethylethyl)phenyl]-, (2E)-RefChem:556947
Show more names
9810CS-2548AMG-9810 ，S6934AMG9810, 10 mM in DMSOAMG 9810 >=98% (HPLC), powder(2E)-N-(2，3-Dihydro-1，4-benzodiAMG 9810, TRPV1 receptor antagonist3-[4-(TERT-BUTYL)PHENYL]-N-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)ACRYLAMIDE
DTXCID201476723637-276-2DTXSID40202960(E)-3-(4-(tert-butyl)phenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamideMFCD00955103(2E)-N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenamideCHEMBL195789HMS3263D18
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 47.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 474
Physicochemical properties
- Boiling point
- 512.5 · 512.5±50.0 °C(Predicted)
- Density
- 1.175 · 1.175±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL · DMSO: >5mg/mL
- pka
- 12.22 · 12.22±0.20(Predicted)
- form
- powder
- color
- white to beige
- InChI
- 1S/C21H23NO3/c1-21(2,3)16-7-4-15(5-8-16)6-11-20(23)22-17-9-10-18-19(14-17)25-13-12-24-18/h4-11,14H,12-13H2,1-3H3,(H,22,23)/b11-6+
- InChIKey
- GZTFUVZVLYUPRG-IZZDOVSWSA-N
- SMILES
- CC(C)(C)c1ccc(\C=C\C(=O)Nc2ccc3OCCOc3c2)cc1
- FDA UNII
- 182 HIJ2D7F · 182HIJ2D7F
- UNSPSC Code
- 12352203 · 12352203
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H413
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H413
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 4
- Precautionary statements
- P264-P270-P273-P301+P312-P501
Chemistry & industry
Applications
DescriptionAMG 9810 is a competitive antagonist of capsaicin activation of the vanilloid receptor 1 (TRPV1) (IC50s = 24.5 and 85.6 nM for human and rat, respectively). Additionally, it has been shown to compete with other modes of TRPV1 activation, including protons (IC50s = 92.7 and 294 nM for human and rat, respectively), heat (IC50s = 15.8 and 21 nM for human and rat, respectively), and the endogenous ligands: anandamide, N-arachidonyl dopamine (IC50s = 8.5 and 260 nM for human and rat, respectively), and oleoyldopamine. In a rat model of inflammatory pain induced by intraplantar injection of complete Freund’s adjuvant, 30-100 mg/kg AMG 9810 reverses thermal and mechanical hyperalgesia.
UsesAMG 9810 is a competitive antagonist of capsaicin activation of the vanilloid receptor 1 (TRPV1) (IC50s = 24.5 and 85.6 nM for human and rat, respectively). Additionally, it has been shown to compete with other modes of TRPV1 activation, including protons (IC50s = 92.7 and 294 nM for human and rat, respectively), heat (IC50s = 15.8 and 21 nM for human and rat, respectively), and the endogenous ligands: anandamide, N-arachidonyl dopamine (IC50s = 8.5 and 260 nM for human and rat, respectively), and oleoyldopamine. In a rat model of inflammatory pain induced by intraplantar injection of complete Freund’s adjuvant, 30-100 mg/kg AMG 9810 reverses thermal and mechanical hyperalgesia.[Cayman Chemical]
Additional notes
DefinitionChEBI: 3-(4-tert-butylphenyl)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-propenamide is a member of cinnamamides and a secondary carboxamide.
Related reactions
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Compound notes
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