Glaucine

Drugbox
IUPAC_name = (S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo [de,g] quinoline


CAS_number = 475-81-0
CAS_supplemental = 5630-11-5
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PubChem = 16754
DrugBank =
chemical_formula =
C=21 | H=25 | N=1 | O=4
molecular_weight = 355.428 g/mol
smiles = CN1CCC2=CC(=C(C3=C2 [C@@H] 1CC4=CC(=C(C=C43)OC)OC)OC)OC
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Glaucine is an alkaloid found in several different plant species such as "Glaucium flavum", "Glaucium oxylobum", [Morteza-Semnani K, Amin G, Shidfar MR, Hadizadeh H, Shafiee A. Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum. "Fitoterapia". 2003 Jul;74(5):493-6. PMID 12837370] "Croton lechleri" [Milanowski DJ, Winter RE, Elvin-Lewis MP, Lewis WH. Geographic distribution of three alkaloid chemotypes of Croton lechleri. "Journal of Natural Products". 2002 Jun;65(6):814-9. PMID 12088421] and "Corydalis yanhusuo". [Xu XH, Yu GD, Wang ZT. Resource investigation and quality evaluation on wild Corydalis yanhusuo. (Chinese). "Zhongguo Zhong Yao Za Zhi". 2004 May;29(5):399-401. PMID 15706885] It has bronchodilator and antiinflammatory effects, acting as a PDE₄ inhibitor and calcium channel blocker, [Cortijo J, Villagrasa V, Pons R, Berto L, Martí-Cabrera M, Martinez-Losa M, Domenech T, Beleta J, Morcillo EJ. Bronchodilator and anti-inflammatory activities of glaucine: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes. "British Journal of Pharmacology". 1999 Aug;127(7):1641-51. PMID 10455321] and is used medically as an antitussive in some countries. [Rühle KH, Criscuolo D, Dieterich HA, Köhler D, Riedel G. Objective evaluation of dextromethorphan and glaucine as antitussive agents. "British Journal of Clinical Pharmacology". 1984 May;17(5):521-4. PMID 6375709] Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images, [Rovinskiĭ VI. A case of hallucinogen-like action of glaucine. (Russian). "Klinicheskaia Meditsina (Mosk)". 1989 Sep;67(9):107-8. PMID 2586025] [Rovinskiĭ VI. Acute glaucine syndrome in the physician's practice: the clinical picture and potential danger. (Russian). "Klinicheskaia Meditsina (Mosk)". 2006;84(11):68-70. PMID 17243616] and has recently been detected as a novel recreational drug. [Dargan PI, Button J, Hawkins L, Archer JR, Ovaska H, Lidder S, Ramsey J, Holt DW, Wood DM. Detection of the pharmaceutical agent glaucine as a recreational drug. "European Journal of Clinical Pharmacology". 2008 May;64(5):553-4. PMID 18204834]

ee Also

*Apomorphine
*Bulbocapnine
*Nuciferine
*Pukateine
*Stepholidine
*Tetrahydropalmatine

References