Basic information
- CAS
57186-25-1- Standard SMILES
CC(C)(O)C1OC2CCC3(C)C(O)(CCC4Cc5c([nH]c6ccccc56)C43C)C2=CC1=O- InChIKey
ACNHBCIZLNNLRS-UHFFFAOYSA-N- Molecular formula
- C27H33NO4
- Average molar mass
- 435.6 g/mol
- Monoisotopic mass
- 435.24095853
Overview
Tremorgenic agent from Penicillium paxilli, Acremonium lorii, Emericella foveolata, Emericella desertorum and Emericella striata Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli. Paxilline belongs to the family of Diterpenes. These are terpene compounds formed by four isoprene units.
Names & identifiers
- Preferred name
- Paxillin
- IUPAC
- 11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one
- English name
- PAXILLINE
- Molecular formula
- C27H33NO4
- Molecular weight
- 435.56
Names & synonyms
paxillinRefChem:3891812H-1-BENZOPYRANO[5',6':6,7]INDENO[1,2-B]INDOL-3(4BH)-ONE, 5,6,6A,7,12,12B,12C,13,14,14A-DECAHYDRO-4B-HYDROXY-2-(1-HYDROXY-1-METHYLETHYL)-12B,12C-DIMETHYL-, (2R,4BS,6AS,12BS,12CR,14AS)-4b-Hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-onepaxilline [M+H]+Compound NP-024130GTPL2309orb3170753BDBM86263ACNHBCIZLNNLRS-UHFFFAOYSA-N2H-Pyrano(2'',3'':5',6')benz(1',2':6,7)indeno(1,2-b)indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-AKOS040737282
Show more names
PAXILINEmycillinPAXILLINEPaxicillinPaxilline solutionPaxilline in MethanolfromPenicilliumpaxilliPAXILLINE, PENICILLIUM PAXILLIpaxilline from penicillium paxilliPaxilline, Ca2+-activated K+channel blocker
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 82.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 868
Physicochemical properties
- Flash point
- 2 ℃ · 2℃
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO, acetone or chloroform.
- form
- powder
- color
- faint yellow
- Major Application
- cleaning productscosmeticsfood and beveragespersonal care
- 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
- FDA UNII
- 3 T9U9Z96L7 · 3T9U9Z96L7
- UNSPSC Code
- 85151701 · 85151701
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331-H315-H318-H335
- Precautionary statements
- 261 · P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
- Hazard Codes
- T,Xn,F
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
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)
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (A2976)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
Chemistry & industry
Uses & manufacturing
UsesPaxilline is a tremorgenic mycotoxin that has been found in fungus Penicillium paxilli. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976, A3082)
Applications
DescriptionA 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.
DescriptionPaxilline is an indole diterpene from fungi which potently and reversibly inhibits large conductance Ca2+-activated K+ (BKCa) channels, as shown in patch clamp (Ki = 1.9 nM) and whole smooth muscle cell studies (Ki = 35.7 nM). It also enhances the binding of charybdotoxin , a peptidyl neurotoxin, to BKCa channels. Paxilline is currently used to evaluate the role of BKCa channels in various cell processes and responses.
UsesPotent blocker of high-conductance calcium-activated potassium (BKCa) channels
UsesPaxilline 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.
Suppliers52 total
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Related reactions
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Compound notes
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