基本情報
- CAS
138977-28-3- 標準SMILES
Oc1cc2c(cc1O)CN(C(=S)NCCc1ccc(Cl)cc1)CCC2- InChIKey
DRCMAZOSEIMCHM-UHFFFAOYSA-N- 分子式
- C19H21ClN2O2S
- 平均分子量
- 376.9 g/mol
- 単同位体質量
- 376.1012268
概要
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.
名称と識別子
- 優先名称
- Capsazepine
- IUPAC
- N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2-benzazepine-2-carbothioamide
- 現地名
- 2-[[2-(4-クロロフェニル)エチルアミノ]チオカルボニル]-2,3,4,5-テトラヒドロ-1H-2-ベンゾアゼピン-7,8-ジオール
- 英語名
- CAPSAZEPINE
- 分子式
- C19H21ClN2O2S
- 分子量
- 376.9
名称と別名
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
名称をさらに表示
カプサゼピン2-[[2-(4-クロロフェニル)エチルアミノ]チオカルボニル]-2,3,4,5-テトラヒドロ-1H-2-ベンゾアゼピン-7,8-ジオール({[2-(4-クロロフェニル)エチル]アミノ}スルファニル)(7,8-ジヒドロキシ-2,3,4,5-テトラヒドロ-1H-2-ベンゾアゼピン-2-イル)メタノンcapasazepineCapsazepine,98%Capsazepine, 10 mM in DMSO
物性
構造計算による物性
- XLogP
- 3.9
- 極性表面積
- 87.8 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 3
- 回転可能結合数
- 3
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 445
物理化学的性質
- 融点
- 155 · 155-157°C
- 沸点
- 581.1 · 581.1±60.0 °C(Predicted)
- 比重(密度)
- 1.35 · 1.350±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- メタノール: 可溶
- 酸解離定数(Pka)
- 9.73 · 9.73±0.20(Predicted)
- 外見
- 個体
- 色
- オフホワイト
- 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 データベース
- 138977 · 138977-28-3(CAS DataBase Reference)
化学的性質
化学的特性Light Yellow Solid
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- 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
- ストレージクラス
- 11 - Combustible Solids
化学と産業
応用分野
説明Transient 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.
使用Capsazepine 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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