131-28-2 Usage
Description
CI 15511, also known as Narceine, is an alkaloid derived from opium (Papaver somniferum). It was first isolated in 1832 and later characterized by Couerbe and Anderson. CI 15511 forms slender, colorless needles or prisms of the trihydrate with a melting point of 170°C. It is optically inactive and dissolves readily in alkalies to form metallic derivatives. As a weak, monoacidic base, it forms well-crystallized salts. The hydrochloride salt crystallizes with 5.5 H2O from cold, dilute HCl, or as the trihydrate from hot solutions. CI 15511 also forms characteristic colors when reacted with chlorine water and ammonia or dilute iodine solution.
Uses
CI 15511 is used as a chemical intermediate in the synthesis of various compounds, such as trimethylamine, hemipinic acid, and 2-cyano-3-methoxy-4:s-methylenedioxy-1-vinylbenzene. It is also used in the development of drug delivery systems and as a research tool in the study of alkaloid chemistry and its applications.
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.