Capsazepine
Grundinformationen
- CAS
138977-28-3- Standard-SMILES
Oc1cc2c(cc1O)CN(C(=S)NCCc1ccc(Cl)cc1)CCC2- InChIKey
DRCMAZOSEIMCHM-UHFFFAOYSA-N- Summenformel
- C19H21ClN2O2S
- Durchschnittliche Molmasse
- 376,9 g/mol
- Monoisotopische Masse
- 376,1012268
Überblick
Capsazepine is a benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist. It has a role as a capsaicin receptor antagonist. It is a member of catechols, a benzazepine, a member of thioureas and a member of monochlorobenzenes.
Namen und Bezeichner
- Bevorzugter Name
- Capsazepine
- IUPAC
- N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2-benzazepine-2-carbothioamide
- Englischer Name
- CAPSAZEPINE
- Summenformel
- C19H21ClN2O2S
- Molmasse
- 376.9
Namen und Synonyme
capsazepine138977-28-3N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamideN-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2-benzazepine-2-carbothioamideLFW48MY844CHEBI:70773DTXSID20160852N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamideN-(2-(4-chlorophenyl)ethyl)-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-Benzazepine-2-carbothioamideN-(2-[4-chlorophenyl]ethyl)-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamideN-(2-(4-chlorophenyl)ethyl)-7,8-dihydroxy-1,3,4,5-tetrahydro-2-benzazepine-2-carbothioamideN-(2-(4-chlorophenyl)ethyl)-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide
Weitere Namen anzeigen
capasazepineCapsazepine,98%Capsazepine, 10 mM in DMSOCapsazepine, TRPV1 antagonistCAPSAZEPINE SYNTHETIC ANALOG OF C8-dihydroxy-2H-2-benzazepine-2-carbothioamide78-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
RefChem:123319DTXCID4083343capsazepinMFCD00153778ST50826300N-(4-chlorophenethyl)-7,8-dihydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide2H-2-Benzazepine-2-carbothioamide, N-[2-(4-chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-CHEMBL391997
Datenbank-Bezeichner
- CAS
138977-28-3- PubChem CID
- 2733484
- DTXSID
DTXSID20160852- ChEMBL
CHEMBL391997- ChEBI
CHEBI:70773- UNII
- LFW48MY844
- Nikkaji
- J837.194F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,9
- Polarare Oberfläche (TPSA)
- 87,8 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 445
Physikochemische Eigenschaften
- Schmelzpunkt
- 155 · 155-157°C
- Siedepunkt
- 581.1 · 581.1±60.0 °C(Predicted)
- Dichte
- 1.35 · 1.350±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- methanol: soluble
- pka
- 9.73 · 9.73±0.20(Predicted)
- Aggregatzustand
- solid
- Farbe
- off-white
- InChI
- InChI=1S/C19H21ClN2O2S/c20-16-5-3-13(4-6-16)7-8-21-19(25)22-9-1-2-14-10-17(23)18(24)11-15(14)12-22/h3-6,10-11,23-24H,1-2,7-9,12H2,(H,21,25)
- InChIKey
- DRCMAZOSEIMCHM-UHFFFAOYSA-N
- SMILES
- N1(C(NCCC2=CC=C(Cl)C=C2)=S)CC2=CC(O)=C(O)C=C2CCC1
- CAS Datenbank
- 138977 · 138977-28-3(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- ridadr
- 2811
- risk_code
- 20/21/22-36/37/38
- hazard_code
- Xn
- safety_code
- 22-24/25-36-26
- hazard_class
- 6.1(a)
- packing_group
- II
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungTransient receptor potential vanilloid type 1 (TRPV1) is a member of the transient receptor potential (TRP) family that is activated or sensitized by a variety of endogenous stimuli as a result of tissue injury and inflammation. TRPV1 is upregulated during inflammation and plays a role in the perception of pain. Capsazepine is a competitive antagonist of transient receptor potential vanilloid type 1 (TRPV1) which blocks the capsaicin-induced uptake of Ca2+ in neonatal rat dorsal root ganglia with an IC50 of 0.42 μM and Chinese hamster ovary cells with an IC50 of 17 nM. It does not block acid- or heat-induced activation of TRPV1 and may block receptors other than TRPV1.
VerwendenCapsazepine is shown to inhibit the development of mechanical hyperalgesia induced by intraplanar capsaicin injection. Capsazepine is described to block Resiniferatoxin (sc-24015)- and Capsaicin-induced contractions of guinea pig treacheal smooth muscle. Studies investigating the function of the VR1 (TRPV1 receptor) have employed Capsazepine as a tool for perturbing systemic neuronal response to Capsaicin.
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Ergänzende Hinweise
DefinitionChEBI: A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of caps icin, it was the first reported capsaicin receptor antagonist.
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