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Protopine

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Protopine
Names
IUPAC name 7-Methyl-2′H,2′′H-7,13a-secobis(dioxolo)berbin-13a-one
Systematic IUPAC name 5-Methyl-4,6,7,14-tetrahydro-2H,10H-bis(benzodioxolo)azecin-13(5H)-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.546 Edit this at Wikidata
EC Number
  • 204-999-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3Key: GPTFURBXHJWNHR-UHFFFAOYSA-N
  • InChI=1/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3Key: GPTFURBXHJWNHR-UHFFFAOYAW
SMILES
  • c15cc3OCOc3cc5CCN(C)Cc2c(CC1=O)ccc4c2OCO4
Properties
Chemical formula C20H19NO5
Molar mass 353.369 g/mol
Appearance white crystals
Density 1.399 g/cm
Melting point 208 °C (406 °F; 481 K)
Solubility in water practically insoluble
Solubility in chloroform 1:15
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Protopine is an alkaloid occurring in opium poppy, Corydalis tubers and other plants of the family papaveraceae, like Fumaria officinalis. Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3)  (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.

It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.

See also

References

  1. The Merck Index (9 ed.). New Jersey: Merck & Co. 1976. p. 1023.
  2. The Free Dictionary: Protopine
  3. Jiang, B; Cao, K; Wang, R (2004). "Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells". European Journal of Pharmacology. 506 (2): 93–100. doi:10.1016/j.ejphar.2004.11.004. PMID 15588728.
  4. Vrba, J.; Vrublova, E.; Modriansky, M.; Ulrichova, J. (2011). "Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR". Toxicology Letters. 203 (2): 135–141. doi:10.1016/j.toxlet.2011.03.015. PMID 21419197.
  5. Hagel, Jillian M; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Ye (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15: 227. doi:10.1186/s12870-015-0596-0. PMC 4575454. PMID 26384972.
  6. Saeed, SA; Gilani, AH; Majoo, RU; Shah, BH (1997). "Anti-thrombotic and anti-inflammatory activities of protopine". Pharmacological Research. 36 (1): 1–7. doi:10.1006/phrs.1997.0195. PMID 9368908.
  7. Protopine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
Opium components
Alkaloids
Morphine group
(Phenanthrenes. Includes opioids)
Isoquinolines
Protopine group
Tetrahydroprotoberberine group
Aporphine group
Phtalide-isoquinolines
α-Naphthaphenanthridines
Other components


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