(2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-デカヒドロ-4bβ-ヒドロキシ-2-(1-ヒドロキシ-1-メチルエチル)-12bβ,12cα-ジメチル-2H-1-ベンゾピラノ[5',6':6,7]インデノ[1,2-b]インドール-3(4bH)-オン
パキシリン · (2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-デカヒドロ-4bβ-ヒドロキシ-2-(1-ヒドロキシ-1-メチルエチル)-12bβ,12cα-ジメチル-2H-1-ベンゾピラノ[5',6':6,7]インデノ[1,2-b]インドール-3(4bH)-オン · パキシリン 100ΜG/ML · (1S,2R,5S,7R,11S,14S)-11-ヒドロキシ-7-(2-ヒドロキシプロパン-2-イル)-1,2-ジメチル-6-オキサ-23-アザヘキサシクロ[12.10.0.02,11.05,10.016,24.017,22]テトラコサ-9,16(24),17,19,21-ペンタエン-8-オン · (2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-デカヒドロ-4bβ-ヒドロキシ-2-(1-ヒドロキシ-1-メチルエチル)-12bβ,12cα-ジメチル-2H-1-ベンゾピラノ[5′,6′:6,7]インデノ[1,2-b]インドール-3(4bH)-オン · PAXILINE · mycillin · PAXILLINE
![(2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-デカヒドロ-4bβ-ヒドロキシ-2-(1-ヒドロキシ-1-メチルエチル)-12bβ,12cα-ジメチル-2H-1-ベンゾピラノ[5',6':6,7]インデノ[1,2-b]インドール-3(4bH)-オン の分子構造式](/img/chemical/4697.png)
識別子と物理属性
| CAS No. | 57186-25-1 |
|---|---|
| 分子式 | C27H33NO4 |
| 平均分子量 | 435.6 g/mol |
| 単同位体質量 | 435.24095853 g/mol |
| SMILES | CC(C)(O)C1OC2CCC3(C)C(O)(CCC4Cc5c([nH]c6ccccc56)C43C)C2=CC1=O |
| InChIKey | ACNHBCIZLNNLRS-UHFFFAOYSA-N |
| PubChem CID | 4697 |
| 現地名 | (2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-デカヒドロ-4bβ-ヒドロキシ-2-(1-ヒドロキシ-1-メチルエチル)-12bβ,12cα-ジメチル-2H-1-ベンゾピラノ[5',6':6,7]インデノ[1,2-b]インドール-3(4bH)-オン |
化学・物理的性質
| XLogP | 3.5 |
|---|---|
| 極性表面積 | 82.6 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 1 |
| 重原子数 | 32 |
| 形式電荷 | 0 |
| 複雑度 | 868 |
| 引火点 | 2℃ |
| 貯蔵条件 | 2-8°C |
| 溶解度 | DMSO、アセトンまたはクロロホルムに可溶。 |
| 外観・状態 | 粉 |
| 色 | かすかな黄色 |
| 主な用途 | 洗浄剤化粧品食品および飲料パーソナルケア |
| InChIKey | ACNHBCIZLNNLRS-UBGQALKQSA-N |
| SMILES | N1C2=C(C=CC=C2)C2C[C@@]3([H])[C@](C)(C1=2)[C@@]1(C)CC[C@]2([H])O[C@H](C(O)(C)C)C(=O)C=C2[C@]1(O)CC3 |
化学的特性
Powder
安全性と法規制
| Treatment | To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (A744) |
|---|---|
| 健康影響 | Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (A2976) |
| 暴露経路 | Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) |
| 毒性の概要 | Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. In addition, paxilline inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Paxilline is also genotoxic and causes DNA damage. (A2976, A2993, A3026) |
| Signs and Symptoms | Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia. (A2976) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | DJ2830000 |
| 輸送番号（UN） | UN 2811 6.1/PG 3 |
| 税関コード | 29419090 |
| 危険文句（R） | 23/24/25-36/37/38-41-36-20/21/22-11 |
| 危険表示 | T,Xn,F |
| 安全措置（S） | 26-36/37/39-45-36/37-16 |
| 危険等級 |
用途
説明
A complex alkaloid, paxilline occurs in the mycelium of the mold Penicillium paxilli. The structure has been confirmed by X-ray crystallography. The crystals are orthorhombic with space group P2 12 121 and a = 31.009, b = 11.522 and c = 7.70 A.
使用
Paxilline is a tremorgenic mycotoxin isolated from species of Penicillium, Acremonium and Emericella. Paxilline selectively blocks high-conductance Ca2+-activated potassium channels and inhibits binding to the cerebellar inositol 1,4,5-triphosphate (InsP(3)) receptor.