Glaucina

Glaucina
Nombre IUPAC
	(S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline
General
Fórmula estructural
Fórmula molecular	H; 25NO; 4
Identificadores
Número CAS	475-81-0
ChEBI	5373
ChEMBL	228082
ChemSpider	15883
PubChem	16754
UNII	NU19306XA7
KEGG	D08014
	SMILES CN1CCc2cc(c(c-3c2[C@@H]1Cc4c3cc(c(c4)OC)OC)OC)OC
	InChI InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1; Key: RUZIUYOSRDWYQF-HNNXBMFYSA-N
Propiedades físicas
Masa molar	355,428 g/mol
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

Glaucina es un alcaloide aislado de diferentes especies de plantas tales como Glaucium flavum,^[2] Glaucium oxylobum,^[3]^[4] Croton lechleri^[5] y Corydalis yanhusuo.^[6]

Tiene propiedades broncodilatadoras y antiinflamatorias, ya que actúa como un inhibidor de la fosfodiesterasa y bloqueando de los canales de calcio.^[7]^[8] Para aprovechar estas propiedades se utiliza a veces, principalmente en la forma de hidrocloruro de glaucina, como un supresor de la tos. Puede tener efectos secundarios como sedación, astenia y provocar alucinaciones visuales sobre todo de color.^[9]^[10] Por esta característica se utiliza a veces como sustancia alucinógena.^[11]

Glaucina (2 estereoisómeros)
(S)-configuración	(R)-configuración

Referencias

↑ Número CAS
↑ G.B. Lapa; O.P. Sheichenko; A.G. Serezhechkin and O.N. Tolkachev (August 2004). «HPLC Determination of Glaucine in Yellow Horn Poppy Grass (Glaucium flavum Crantz)». Pharmaceutical Chemistry Journal 38 (1): 441-442. ISSN 0091-150X. doi:10.1023/B:PHAC.0000048907.58847.c6. Consultado el 14 de junio de 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».
↑ Xu, XH; Yu, GD; Wang, ZT (2004). «Resource investigation and quality evaluation on wild Corydalis yanhusuo». Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 29 (5): 399-401. PMID 15706885.
↑ Morteza-Semnani, K; Amin, G; Shidfar, MR; Hadizadeh, H; Shafiee, A (2003). «Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum». Fitoterapia 74 (5): 493-6. PMID 12837370. doi:10.1016/s0367-326x(03)00113-8.
↑ Milanowski, DJ; Winter, RE; Elvin-Lewis, MP; Lewis, WH (2002). «Geographic distribution of three alkaloid chemotypes of Croton lechleri». Journal of Natural Products 65 (6): 814-9. PMID 12088421. doi:10.1021/np000270v.
↑ 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 (1999). «Bronchodilator and anti-inflammatory activities of glaucine: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes». British Journal of Pharmacology 127 (7): 1641-51. PMC 1566148. PMID 10455321. doi:10.1038/sj.bjp.0702702.
↑ Rühle, KH; Criscuolo, D; Dieterich, HA; Köhler, D; Riedel, G (1984). «Objective evaluation of dextromethorphan and glaucine as antitussive agents». British Journal of Clinical Pharmacology 17 (5): 521-4. PMC 1463443. PMID 6375709. doi:10.1111/j.1365-2125.1984.tb02384.x.
↑ Rovinskiĭ, VI (1989). «A case of hallucinogen-like action of glaucine». Klinicheskaia meditsina 67 (9): 107-8. PMID 2586025.
↑ Rovinskiĭ, VI (2006). «Acute glaucine syndrome in the physician's practice: The clinical picture and potential danger». Klinicheskaia meditsina 84 (11): 68-70. PMID 17243616.
↑ Dargan, PI; Button, J; Hawkins, L; Archer, JR; Ovaska, H; Lidder, S; Ramsey, J; Holt, DW; Wood, DM (2008). «Detection of the pharmaceutical agent glaucine as a recreational drug». European journal of clinical pharmacology 64 (5): 553-4. PMID 18204834. doi:10.1007/s00228-007-0451-9.

Datos: Q2398298
Multimedia: Glaucine / Q2398298

[1] Número CAS

[2] G.B. Lapa; O.P. Sheichenko; A.G. Serezhechkin and O.N. Tolkachev (August 2004). «HPLC Determination of Glaucine in Yellow Horn Poppy Grass (Glaucium flavum Crantz)». Pharmaceutical Chemistry Journal 38 (1): 441-442. ISSN 0091-150X. doi:10.1023/B:PHAC.0000048907.58847.c6. Consultado el 14 de junio de 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».

[3] Xu, XH; Yu, GD; Wang, ZT (2004). «Resource investigation and quality evaluation on wild Corydalis yanhusuo». Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 29 (5): 399-401. PMID 15706885.

[4] Morteza-Semnani, K; Amin, G; Shidfar, MR; Hadizadeh, H; Shafiee, A (2003). «Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum». Fitoterapia 74 (5): 493-6. PMID 12837370. doi:10.1016/s0367-326x(03)00113-8.

[5] Milanowski, DJ; Winter, RE; Elvin-Lewis, MP; Lewis, WH (2002). «Geographic distribution of three alkaloid chemotypes of Croton lechleri». Journal of Natural Products 65 (6): 814-9. PMID 12088421. doi:10.1021/np000270v.

[6] 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

[Missingor-7] Cortijo, J; Villagrasa, V; Pons, R; Berto, L; Martí-Cabrera, M; Martinez-Losa, M; Domenech, T; Beleta, J; Morcillo, EJ (1999). «Bronchodilator and anti-inflammatory activities of glaucine: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes». British Journal of Pharmacology 127 (7): 1641-51. PMC 1566148. PMID 10455321. doi:10.1038/sj.bjp.0702702.

[8] Rühle, KH; Criscuolo, D; Dieterich, HA; Köhler, D; Riedel, G (1984). «Objective evaluation of dextromethorphan and glaucine as antitussive agents». British Journal of Clinical Pharmacology 17 (5): 521-4. PMC 1463443. PMID 6375709. doi:10.1111/j.1365-2125.1984.tb02384.x.

[9] Rovinskiĭ, VI (1989). «A case of hallucinogen-like action of glaucine». Klinicheskaia meditsina 67 (9): 107-8. PMID 2586025.

[Missingor_b-10] Rovinskiĭ, VI (2006). «Acute glaucine syndrome in the physician's practice: The clinical picture and potential danger». Klinicheskaia meditsina 84 (11): 68-70. PMID 17243616.

[Missingor_a-11] Dargan, PI; Button, J; Hawkins, L; Archer, JR; Ovaska, H; Lidder, S; Ramsey, J; Holt, DW; Wood, DM (2008). «Detection of the pharmaceutical agent glaucine as a recreational drug». European journal of clinical pharmacology 64 (5): 553-4. PMID 18204834. doi:10.1007/s00228-007-0451-9.

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