Narcein

Structural formula
General
Surname	Narcein
other names	Narceinum 6- {2- [6- (2-Dimethylaminoethyl) -4-methoxy-1,3-benzodioxol-5-yl] acetyl} -2,3-dimethoxybenzoic acid
Molecular formula	C 23 H 27 NO 8
External identifiers / databases
CAS number 131-28-2 EC number 205-021-0 ECHA InfoCard 100.004.566 PubChem 8564 ChemSpider 8246 Wikidata Q907355
properties
Molar mass	445.46 g · mol -1
Physical state	firmly
Melting point	138 ° C
solubility	poor in water (780 mg l −1 at 13 ° C)
safety instructions
GHS hazard labeling no classification available
Toxicological data	2000 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Narcein is an opiate ; its share in opium is 0.1–0.2%. It was previously used as a hypnotic and narcotic . Narcein is weaker than morphine , but potentiates its effects many times over in combination. Narcein esters (e.g. the ethyl ester ) were also used.

Opium poppy, Papaver somniferum , from whose milk narcein - among other alkaloids - can be isolated.

Narceine can be obtained partially synthetically from noscapine by methylating the nitrogen atom to the quaternary ammonium ion , converting it into the hydroxide and heating (analogous to Hofmann degradation ).

Individual evidence

1. ↑ ^{a b c} Entry on narcein in the ChemIDplus database of the United States National Library of Medicine (NLM) .
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ↑ Harry Auterhoff : Textbook of Pharmaceutical Chemistry , Wissenschaftliche Verlagsgesellschaft Stuttgart, 1968.