CAS 475-81-0|Glaucine
Introduction：Basic information about CAS 475-81-0|Glaucine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Glaucine | ||
|---|---|---|---|
| CAS Number | 475-81-0 | Molecular Weight | 355.427 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 487.0±45.0 °C at 760 mmHg |
| Molecular Formula | C21H25NO4 | Melting Point | 246-247ºC |
| MSDS | / | Flash Point | 140.2±25.9 °C |
Names
| Name | (S)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline |
|---|---|
| Synonym | More Synonyms |
Glaucine BiologicalActivity
| Description | Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum Crantz with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 µM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>Calcium ChannelSignaling Pathways >>Anti-infection >>Influenza VirusSignaling Pathways >>Metabolic Enzyme/Protease >>Phosphodiesterase (PDE)Research Areas >>InfectionSignaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorSignaling Pathways >>GPCR/G Protein >>Dopamine ReceptorResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Neuronal Signaling >>Dopamine Receptor |
| Target | Ki: 3.4 µM (Phosphodiesterase 4 (PDE4))[1] α-adrenoceptor[1] Ca2+ channel[1] Dopamine D1/D2 receptors[2] |
| References | [1]. J Cortijo, et al. Bronchodilator and Anti-Inflammatory Activities of Glaucine: In Vitro Studies in Human Airway Smooth Muscle and Polymorphonuclear Leukocytes. Br J Pharmacol. 1999 Aug;127(7):1641-51. [2]. Golo M J Meyer, et al. Studies on the in Vivo Contribution of Human Cytochrome P450s to the Hepatic Metabolism of Glaucine, a New Drug of Abuse. Biochem Pharmacol. 2013 Nov 15;86(10):1497-506. [3]. Maya Spasova, et al. Cinnamoyl- And Hydroxycinnamoyl Amides of Glaucine and Their Antioxidative and Antiviral Activities. Bioorg Med Chem. 2008 Aug 1;16(15):7457-61. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 487.0±45.0 °C at 760 mmHg |
| Melting Point | 246-247ºC |
| Molecular Formula | C21H25NO4 |
| Molecular Weight | 355.427 |
| Flash Point | 140.2±25.9 °C |
| Exact Mass | 355.178345 |
| PSA | 40.16000 |
| LogP | 3.86 |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| Index of Refraction | 1.576 |
| InChIKey | RUZIUYOSRDWYQF-HNNXBMFYSA-N |
| SMILES | COc1cc2c(cc1OC)-c1c(OC)c(OC)cc3c1C(C2)N(C)CC3 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 545 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 143 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 434 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 167 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 430 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 31,44,1968
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - guinea pig
- DOSE/DURATION :
- 140 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 6300 mg/kg/12W-I
- TOXIC EFFECTS :
- Liver - liver function tests impaired
- REFERENCE :
- FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 46(4),100,1983
Safety Information
| Hazard Codes | Xi |
|---|---|
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Synonyms
| (6aS)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline |
| 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (S)- |
| (S)-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline |
| (+)-Glaucine |
| 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (6aS)- |
| d-Glaucine |
| 6aα-Aporphine, 1,2,9,10-tetramethoxy- |
| Glaucine |
| EINECS 207-501-5 |
