Glaucine

Title: Glaucine
CAS Registry Number: 475-81-0
CAS Name: (6aS)-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline
Additional Names: 1,2,9,10-tetramethoxyaporphine; boldine dimethyl ether
Trademarks: Bromcholitin; Glauvent
Molecular Formula: C21H25NO4
Molecular Weight: 355.43
Percent Composition: C 70.96%, H 7.09%, N 3.94%, O 18.01%
Literature References: d-Form prevalent in nature. Found in Glaucium flavum Crantz (G. luteum Scop.), Papaveraceae and in Dicentra and Corydalis species, Fumariaceae. Isoln: Fischer, Arch. Pharm. 239, 426 (1901). Structure and prepn: Gadamer, ibid. 249, 680 (1911); Späth, Tharrer, Ber. 66, 904 (1933). Configuration: Faltis, Adler, Arch. Pharm. 284, 281 (1951). Synthesis of dl-form: Chan, Maitland, J. Chem. Soc. C 1966, 753; Jackson, Martin, ibid. 2061; Cava et al., J. Org. Chem. 35, 175 (1970). Pharmacology and toxicity of dl-glaucine phosphate: Y. Kasé et al., Arzneim.-Forsch. 33, 936 (1983). Sites of antitussive action: eidem, ibid. 947.
Properties: Orthorhombic plates, prisms from ethyl acetate or ether, mp 120°. [a]D20 +115° (c = 3 in alc). Sol in acetone, alcohol, chloroform, ethyl acetate. Moderately sol in ether, petr ether. Practically insol in water and benzene.
Melting point: mp 120°
Optical Rotation: [a]D20 +115° (c = 3 in alc)
Derivative Type: Hydrochloride trihydrate
Molecular Formula: C21H25NO4.HCl.3H2O
Molecular Weight: 445.93
Percent Composition: C 56.56%, H 7.23%, N 3.14%, O 25.12%, Cl 7.95%
Properties: Needles. mp 232° (anhydrous). Sol in water, alcohol, chloroform.
Melting point: mp 232° (anhydrous)
Derivative Type: Hydrobromide
Molecular Formula: C21H25NO4.HBr
Molecular Weight: 436.34
Percent Composition: C 57.80%, H 6.01%, N 3.21%, O 14.67%, Br 18.31%
Properties: Crystals, mp 235°. Less sol than the hydrochloride.
Melting point: mp 235°
Derivative Type: dl-Form phosphate
Manufacturers' Codes: DL-832
Molecular Formula: (C21H25NO4)2.3H3PO4
Molecular Weight: 1004.84
Percent Composition: C 50.20%, H 5.92%, N 2.79%, O 31.84%, P 9.25%
Properties: Crystalline powder. LD50 in mice (mg/kg): 98 i.v.; 401 orally (Kasé).
Toxicity data: LD50 in mice (mg/kg): 98 i.v.; 401 orally (Kasé)
Gliadin Glibornuride Gliclazide Gliotoxin Glipizide

Glaucine
Glaucine.svg
Systematic (IUPAC) name
(S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 475-81-0 YesY
5630-11-5
ATC code None
PubChem CID 16754
ChemSpider 15883 N
UNII NU19306XA7 N
KEGG D08014 N
ChEMBL CHEMBL228082 N
NIAID ChemDB 011385
Chemical data
Formula C21H25NO4 
Mol. mass 355.428 g/mol
 N (what is this?)  (verify)

Glaucine is an alkaloid found in several different plant species in the Papaveraceae family such as Glaucium flavum,[1] Glaucium oxylobum and Corydalis yanhusuo,[2][3] and in other plants like Croton lechleri in the family Euphorbiaceae.[4]

It has bronchodilator and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker,[5] and is used medically as an antitussive in some countries.[6] Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images,[7][8] and has recently been detected as a novel recreational drug.[9]