Glaucina

Glaucina
Nome IUPAC
	(S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline
Caratteristiche generali
Formula bruta o molecolare	C21H25NO4
Massa molecolare (u)	355.428 g/mol
Numero CAS	475-81-0
Numero EINECS	207-501-5
PubChem	16754
SMILES	CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)OC)OC
Indicazioni di sicurezza
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La glaucina è un alcaloide isolato in diverse specie di piante quali Glaucium flavum ^[1], Glaucium oxylobum ^[2], Croton lechleri ^[3] e Corydalis yanhusuo ^[4].

Ha proprietà broncodilatatrici e antinfiammatorie, agendo come inibitore della fosfodiesterasi e calcio-antagonista ^[5]. Per queste sue proprietà viene talora impiegata, per lo più in forma di idrocloridrato di glaucina, come sedativo della tosse ^[6]. Può avere effetti collaterali come sedazione, astenia e può rivelarsi un allucinogeno in grado di stimolare sensazioni visive particolarmente colorate ^[7]^[8]. Per tale caratteristica è talora utilizzata come sostanza d'abuso ^[9].

Glaucina (2 Isomeria)
(S)-configurazione	(R)-configurazione

Note

^ G.B. Lapa; O.P. Sheichenko; A.G. Serezhechkin and O.N. Tolkachev, HPLC Determination of Glaucine in Yellow Horn Poppy Grass (Glaucium flavum Crantz) ^{[collegamento interrotto]}, in Pharmaceutical Chemistry Journal, vol. 38, n. 1, agosto 2004, pp. 441-442, DOI:10.1023/B:PHAC.0000048907.58847.c6, ISSN 0091-150X (WC · ACNP). URL consultato il 14 giugno 2009.
«S-(+)-Glaucine (C₂₁H₂₅NO₄) is the main alkaloid component in the grass of yellow horn poppy (Glaucium luteum L., syn. Glaucium flavum Crantz) of the Papaveraceae family»
^ 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
^ 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
^ 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
^ 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
^ 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
^ 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
^ 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

Altri progetti

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Portale Chimica

Portale Medicina

[1] G.B. Lapa; O.P. Sheichenko; A.G. Serezhechkin and O.N. Tolkachev, HPLC Determination of Glaucine in Yellow Horn Poppy Grass (Glaucium flavum Crantz) ^{[collegamento interrotto]}, in Pharmaceutical Chemistry Journal, vol. 38, n. 1, agosto 2004, pp. 441-442, DOI:10.1023/B:PHAC.0000048907.58847.c6, ISSN 0091-150X (WC · ACNP). URL consultato il 14 giugno 2009.
«S-(+)-Glaucine (C₂₁H₂₅NO₄) is the main alkaloid component in the grass of yellow horn poppy (Glaucium luteum L., syn. Glaucium flavum Crantz) of the Papaveraceae family»

[2] 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

[3] 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

[4] 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

[5] 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

[6] 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

[7] Rovinskiĭ VI. A case of hallucinogen-like action of glaucine. (Russian). Klinicheskaia Meditsina (Mosk). 1989 Sep;67(9):107-8. PMID 2586025

[8] 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

[9] 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

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