Protopine
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IUPAC name 7-Methyl-2′H,2′′H-7,13a-secobis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-13a-one | |
Systematic IUPAC name 5-Methyl-4,6,7,14-tetrahydro-2H,10H-bis([1,3]benzodioxolo)[4,5-c:5′,6′-g]azecin-13(5H)-one | |
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ECHA InfoCard | 100.004.546 ![]() |
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Properties | |
Chemical formula | C20H19NO5 |
Molar mass | 353.369 g/mol |
Appearance | white crystals |
Density | 1.399 g/cm3 |
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 [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Protopine is an alkaloid occurring in opium poppy,[2] Corydalis tubers[3] and other plants of the family papaveraceae, like Fumaria officinalis.[4] 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.[5]
It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.[6][7]
See also
References
- ^ The Merck Index (9 ed.). New Jersey: Merck & Co. 1976. p. 1023.
- ^ The Free Dictionary: Protopine
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Protopine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
- v
- t
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- 16-Hydroxythebaine
- Berberine
- Canadine
- Codamine
- Coptisine
- Coreximine
- Cycloartenone
- Cyclolaudenol
- Dehydroreticuline
- Dihydrosanguinarine
- Glaucine
- Isoboldine
- Isocorypalmine
- Laudanidine
- Magnoflorine
- Narceine
- Narceinone
- Norlaudanosoline
- Norsanguinarine
- Oripavine
- Oxysanguinarine
- Palaudine
- Papaverrubine B (O-methyl-porphyroxine)
- Papaverrubine C (epiporphyroxine)
- Reticuline
- Salutaridine (sinoacutine)
- Sanguinarine
- Scoulerine
- Somniferine
- Stepholidine
(Phenanthrenes. Includes opioids)
- Codeine
- Morphine
- Narcotoline
- Neopine
- Perparin
- Papaverrubine D (porphyroxine)
- Pseudocodeine
- Pseudomorphine
- Thebaine
- Cotarnine
- Eupaverine
- Hydrocotarnine
- Laudanosine
- Laudanine
- Noscapine (narcotine)
- Papaverine
- Papaveraldine
- Xanthaline
- α-Allocryptopine
- Corycavamine
- Corycavine
- Cryptopine
- Protopine
- Corydaline
- Corybulbine
- Isocorybulbine
- Capaurine
- Dicentrine
- Glaucine
- Corytuberine
- Cularine
- Corydine
- Isocorydine
- Bulbocapnine
- Adulmine
- Bicuculline
- Bicucine
- Corlumine
- Chelidonine
- β-Homochelidonoine
- Chelerythrine
- Sanguinarine
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