Shanghai Nianxing Industrial Co., Ltd
China
Product Name: Glaucine
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BioBioPha
China
Product Name: Glaucine
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Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Glaucine
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DC Chemicals Limited
China
Product Name: Glaucine
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475-81-0

475-81-0 structure

Name: Glaucine
Chemical Name: (S)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
CAS Number: 475-81-0
Molecular Formula: C₂₁H₂₅NO₄
Molecular Weight: 355.427
Catalog: Natural product Alkaloid
Create Date: 2018-06-21 12:19:27
Modify Date: 2024-01-03 08:38:56
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].

Name	(S)-1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
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

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 Channel Signaling Pathways >> Anti-infection >> Influenza Virus Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Research Areas >> Infection Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor Research Areas >> Inflammation/Immunology Signaling 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.

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

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CE0925000

CHEMICAL NAME :: 6a-alpha-Aporphine, 1,2,9,10-tetramethoxy-

CAS REGISTRY NUMBER :: 475-81-0

LAST UPDATED :: 199512

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C21-H25-N-O4

MOLECULAR WEIGHT :: 355.47

HEALTH HAZARD DATA

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

Hazard Codes	Xi
HS Code	2933990090

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%

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