131-28-2 Usage
Description
An alkaloid of opium (Papaver somniferum) was first isolated by Pelletier in
1832 but not characterized until some years later by Couerbe and Anderson, the
latter assigning to it the formula C23H2909N which was accepted until Freund
showed that it contains H20 of crystallization. The base remains in the mother
liquors after removal of the major alkaloids. It forms slender, colourless needles
or prisms of the trihydrate, m.p. 170°C. It is optically inactive and dissolves
readily in alkalies forming metallic derivatives. It behaves as a weak, monoacidic
base forming well-crystallized salts. The hydrochloride crystallizes with 5.5 H20
from cold, dilute HCI, or as the trihydrate from hot solutions. From MeOH it
yields crystals with 1 mole of solvent, m.p. 190-2°C. The aurichloride forms
reddish-yellow needles, m.p. 130°C and the picrate has m.p. 195°C. With chlorine
water, followed by the addition of ammonia, it gives a characteristic blood-red
colour while with dilute iodine solution, the solid alkaloid develops a blue
colour. With ethyl nitrite, narceine forms an oximino derivative which, on
exhaustive methylation, furnishes trimethylamine, hemipinic acid and 2-cyano-3-
methoxy-4: s-methylenedioxy-1-vinylbenzene.
Purification Methods
Recrystallise Narcein from water (as trihydrate). The styphnate has m 185-189o (from EtOH), and the picrate has m 200o (from EtOH). [Beilstein 19 H 370, 19 I 797, 19 II 386, 19 IV 4382.]
References
Couerbe., Annalen, 17,171 (1836)Anderson., ibid, 86, 182 (1853)Roser., ibid, 247, 167 (1888)Freund, Frankforter., ibid, 277,20 (1893)Freund, Oppenheimer., Ber., 42, 1084 (1909)
Check Digit Verification of cas no
The CAS Registry Mumber 131-28-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 1 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 131-28:
(5*1)+(4*3)+(3*1)+(2*2)+(1*8)=32
32 % 10 = 2
So 131-28-2 is a valid CAS Registry Number.
InChI:InChI=1/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)
131-28-2Relevant articles and documents
Secophthalideisoquinolines
Blasko, Gabor,Elango, Varadaraj,Sener, Bilge,Freyer, Alan J.,Shamma, Maurice
, p. 880 - 885 (2007/10/02)
The secophthalideisoquinolines can be subdivided into enol lactones, keto acids, diketo acids, and ene lactams.The diastereomeric β- and α-hydrastine methiodides (8 and 9) supply stereoselectively Z and E enol lactones 11 and 12, respectively, in a syn β-elimination process.N-Methylhydrastine (11) reacts under mild conditions with methanol, water, or ammonia to produce keto ester 18, keto acid 17, or hydroxy lactam 36, respectively.Treatment of hydroxy lactam 36 with acid results in rapid loss of water and formation of the Z ene lactam 33.Photoequilibration of 33gives rise to a mixture of Z and E ene lactams 33 and 34.A biogenetic scheme is proposed for the secophthalideisoquinolines which includes the following sequence: classical phthalideisoquinoline -> phthalideisoquinoline N-metho salt -> secophthalide enol lactone -> secophthalide keto acid -> secophthalide diketo acid -> fumariflorine-type alkaloid.Ene lactams 30-33, as well as the hydroxy lactam fumschleicherine (35), are most probably artifacts of isolation.