Protopine

Protopine[1]

Names
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

Identifiers

CAS Number

* 130-86-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:16415 N

ChEMBL |

* ChEMBL486179 N

ChemSpider |

* 4799 N

EC Number |

* 204-999-6

KEGG |

* C05189 N

PubChem CID

* 4970

UNII |

* UIW569HT35 Y

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,4-6,9-11H2,1H3 N

Key: GPTFURBXHJWNHR-UHFFFAOYSA-N 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,4-6,9-11H2,1H3

Key: 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/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).

N verify (what is YN ?)
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

* Protopine 6-monooxygenase
* Cryptopine
* Bürgi-Dunitz angle

## 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 et al. (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology 15: 227. doi:10.1186/s12870-015-0596-0. PMID 26384972. PMC 4575454. http://openlib.tugraz.at/download.php?id=564f2fa60a35b&location=browse.
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 US National Library of Medicine Medical Subject Headings (MeSH)

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*[CID]: Compound ID