Narcotine Chemical Properties

Melting point:

174-176 °C(lit.)

alpha 

-200 º (c=1 in chloroform)

Boiling point:

532.6°C (rough estimate)

Density 

1.395

refractive index 

1.5614 (estimate)

storage temp. 

-20°C Freezer, Under Inert Atmosphere

solubility 

Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.

pka

7.8(at 25℃)

color 

Orthorhombic prisms or stout needles from alc

optical activity

[α]20/D 200°, c = 1 in chloroform

Water Solubility 

302.9mg/L(25 ºC)

Merck 

13,6752

NIST Chemistry Reference

Narcotine alkaloid(128-62-1)

EPA Substance Registry System

1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)- (128-62-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

RIDADR 

1544

WGK Germany 

3

RTECS 

RD2625000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29329990

Hazardous Substances Data

128-62-1(Hazardous Substances Data)

Toxicity

cyt-ham:lng 100 mg/L ATSUDG (4),41,80

MSDS

• Language:English Provider:SigmaAldrich

Narcotine Usage And Synthesis

Description

A major constituent of opium (Papaver sornni!erurn), this phthalideisolquinoline base was probably first discovered by Derosne, but initially characterized by Robiquet who gave it the formula C23H3S0 7N, changed to that now accepted by Matthiesen and Foster. It crystallizes in colourless needles from EtOH and has [α]_D - 198° (c 1.0, CHC13); - 146° (c 2.0, toluene); - 147° (c 1.59, C6H6) and + 50° (1 % HCl). The alkaloid is a weak, monoacidic, tertiary base, forming unstable salts with acids which are dissociated with H20. The hydrochloride crystallizes with varying amounts of H20, is very soluble in water, readily decomposing into basic salts on standing. The platinichloride is amorphous; the oxalate has m.p. 174°C;[α]²⁰_D + 39.5° (H20); the phthalate, m.p. 160°C; [α]²²_D + 115° (CHC13); sesquisulphate, colourless crystals of the hexahydrate and the picrate, m.p. 1 74-S°C. The (+)-bromocamphorsulphonate has m.p. 110- 120°C; [α]_D + 100.7° (CHC13) and the corresponding (-)-bromocamphorsul_x0002_phonate, m.p. l80.SoC; [α]_D + 29° (CHC13). The alkaloid yields an N-oxide which is a hygroscopic solid; [α]_D + 135° (CHC13) furnishing a crystalline hydrochloride, m.p. 193°C; platinichloride, m.p. 175°C and a picrate, m.p. 130°C.
The base is unstable to heat and when heated in a sealed tube yields a mixture of dimethylnornarcotine, methylnornarcotine and nornarcotine. On heating with H20 and 150°C, or on boiling with dilute acids, it is hydrolyzed to opianic acid and hydrocotarnine. Similar degradations are brought about by acid oxidation orreduction, e.g. Zn and dilute HCl gives hydrocotarnine and meconin while dilute HN03 yields cotarnine and opianic acid. Pharmacologically, narcotine resembles thebaine (q.v.) in its action, being a reflex stimulant rather than a narcotic.

Chemical Properties

Crystalline Solid

Uses

antiacne, antiproliferative agent

Uses

Antitussive.

Definition

ChEBI: A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from p ants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.

brand name

Tusscapine (Fisons);Bequitussin;Bisolvon compositum;Broncha-tulisan eucalyptol;Broncho-tulisan eucalyptol;Brosolin-rectocap;Codipect;Codyl cum expectoras;Coscotab;Degoran;Dettuso;Difimetus compositum;Finipect;Hederix;Lyabex retard;Nipaxan;Nitepax;Nosaclin;Noscalin;Noscapect;Noscarex;Noscatuss;Reatos;Rectolmin bronquial;Ribelfan;Stilco;Teletux;Tucotin;Tuscapin;Tussamine plus;Tussanil n;Tusscalman;Tussicure;Tussisedal;Tussoretard.

World Health Organization (WHO)

Noscapine, a centrally-acting cough suppressant and one of several alkaloids present in papaveretum (opium concentrate) was introduced into medicine many years ago. Subsequently, it was shown to increase the number of chromosomes in mammalian cell lines maintained in vitro. Although the clinical significance of this finding is uncertain, restrictive action was taken in a few countries since the possibility of a genotoxic effect cannot be excluded. On 4 December 1992 the European Committee on Proprietary Medicinal Products concluded that the available evidence does not indicate that use of noscapine holds any significant hazard. The Swedish Medical Products Agency also concluded that there is no justification to restrict the use of noscapine in women of childbearing age.

Biological Functions

Noscapine is a naturally occurring product of the opium poppy. It is a benzylisoquinoline with no analgesic or other CNS effects. Its antitussive effects are weak, but it is used in combination with other agents in mixtures for cough relief.

Hazard

Narcotic, use legally restricted.

Safety Profile

Moderately toxic by ingestion andsubcutaneous routes. Mutation data reported. Anantitussive. When heated to decomposition it emits toxicfumes of NOx.

References

Robiquet., Ann. Chim. Phys., 5,275 (1817)
Matthiessen, Foster.,!. Chern. Soc., 16,342 (1863)
Perkin, Robinson., ibid, 99,775 (1911)
Polonovski, Polonovski., Bull. Soc. Chim. Fr., 47, 361 (1930)
Lovell., Acta Cryst., 6, 869 (1953)
Barnes., Can. f. Chern., 33,444 (1955)
Safe, Moir., ibid, 160 (1964)
Stereochemistry: Battersby, Spenser., Tetrahedron Lett., 11 (1964)

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