Glaucine

Glaucine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
IUPAC name
  • (S)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo[de,g]quinoline
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.006.820
Chemical and physical data
FormulaC21H25NO4
Molar mass355.434 g·mol−1
3D model (JSmol)
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 N
  • Key:RUZIUYOSRDWYQF-HNNXBMFYSA-N N
 NY (what is this?)  (verify)

Glaucine (also known as 1,2,9,10-tetramethoxyaporphine, bromcholitin, glauvent, tusidil, and tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae, such as Glaucium flavum,[1] Glaucium oxylobum, and Corydalis yanhusuo,[2][3] and in other plants such as Croton lechleri in the family Euphorbiaceae.[4]

It has bronchodilator, neuroleptic[5] and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker,[6] and is used medically as an antitussive in some countries.[7] TLRs plays role in its anti inflammatory effects.[8] Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images,[9][10] and has been detected as a novel psychoactive drug.[11] In a 2019 publication,[12] the isomer (R)-glaucine is reported to be a positive allosteric modulator of the 5-HT2A receptor, which is also associated with the hallucinogenic effects of substances such as psilocybin and mescaline.

  1. ^ Lapa GB, Sheichenko OP, Serezhechkin AG, Tolkachev ON (August 2004). "HPLC Determination of Glaucine in Yellow Horn Poppy Grass (Glaucium flavum Crantz)". Pharmaceutical Chemistry Journal. 38 (1): 441–442. doi:10.1023/B:PHAC.0000048907.58847.c6. ISSN 0091-150X. S2CID 44040818. S-(+)-Glaucine (C21H25NO4) is the main alkaloid component in the grass of yellow horn poppy (Glaucium luteum L., syn. Glaucium flavum Crantz) of the family Papaveraceae
  2. ^ Xu XH, Yu GD, Wang ZT (May 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.
  3. ^ Morteza-Semnani K, Amin G, Shidfar MR, Hadizadeh H, Shafiee A (July 2003). "Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum". Fitoterapia. 74 (5): 493–6. doi:10.1016/s0367-326x(03)00113-8. PMID 12837370.
  4. ^ Milanowski DJ, Winter RE, Elvin-Lewis MP, Lewis WH (June 2002). "Geographic distribution of three alkaloid chemotypes of Croton lechleri". Journal of Natural Products. 65 (6): 814–9. Bibcode:2002JNAtP..65..814M. doi:10.1021/np000270v. PMID 12088421.
  5. ^ Zetler G (1988). "Neuroleptic-like, anticonvulsant and antinociceptive effects of aporphine alkaloids: bulbocapnine, corytuberine, boldine and glaucine". Archives Internationales de Pharmacodynamie et de Therapie. 296: 255–281. PMID 2907279.
  6. ^ Cortijo J, Villagrasa V, Pons R, Berto L, Martí-Cabrera M, Martinez-Losa M, et al. (August 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. doi:10.1038/sj.bjp.0702702. PMC 1566148. PMID 10455321.
  7. ^ Rühle KH, Criscuolo D, Dieterich HA, Köhler D, Riedel G (May 1984). "Objective evaluation of dextromethorphan and glaucine as antitussive agents". British Journal of Clinical Pharmacology. 17 (5): 521–4. doi:10.1111/j.1365-2125.1984.tb02384.x. PMC 1463443. PMID 6375709.
  8. ^ Remichkova M, Dimitrova P, Philipov S, Ivanovska N (October 2009). "Toll-like receptor-mediated anti-inflammatory action of glaucine and oxoglaucine" (PDF). Fitoterapia. 80 (7): 411–4. doi:10.1016/j.fitote.2009.05.016. PMID 19481591.
  9. ^ Rovinskiĭ VI (September 1989). "[A case of hallucinogen-like action of glaucine]". Klinicheskaia Meditsina. 67 (9): 107–8. PMID 2586025.
  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.
  11. ^ Dargan PI, Button J, Hawkins L, Archer JR, Ovaska H, Lidder S, et al. (May 2008). "Detection of the pharmaceutical agent glaucine as a recreational drug". European Journal of Clinical Pharmacology. 64 (5): 553–4. doi:10.1007/s00228-007-0451-9. PMID 18204834. S2CID 21348503.
  12. ^ Heng, HL, Chee, CF, Thy, CK, et al. In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5‐HT2 and α1 receptors. Chem Biol Drug Des. 2019; 93: 132– 138. https://doi.org/10.1111/cbdd.13390
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.