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Narcotine

CAS No.
128-62-1
Chemical Name:
Narcotine
Synonyms
Opian;Capval;Lyobex;Ecasil;Terial;Vadebe;Nipaxon;Detusso;nsc5366;Opianin
CBNumber:
CB8468501
Molecular Formula:
C22H23NO7
Molecular Weight:
413.42
MDL Number:
MFCD00069316
MOL File:
128-62-1.mol
MSDS File:
SDS
Last updated:2023-05-18 11:31:16

Narcotine 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
EWG's Food Scores 1-4
FDA UNII 8V32U4AOQU
NIST Chemistry Reference Narcotine alkaloid(128-62-1)
ATC code R05DA07
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

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H336
Precautionary statements  P301+P312+P330
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
Toxicity cyt-ham:lng 100 mg/L ATSUDG (4),41,80

Narcotine price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 363960 (S,R)-Noscapine 97% 128-62-1 5g $83 2024-03-01 Buy
Sigma-Aldrich 1474504 Noscapine United States Pharmacopeia (USP) Reference Standard 128-62-1 100mg $261.6 2024-03-01 Buy
Sigma-Aldrich N1300000 Noscapine European Pharmacopoeia (EP) Reference Standard 128-62-1 n1300000 $220 2024-03-01 Buy
TRC N882000 Noscapine 128-62-1 5g $120 2021-12-16 Buy
Biosynth Carbosynth FN09246 Noscapine base 128-62-1 25g $150 2021-12-16 Buy
Product number Packaging Price Buy
363960 5g $83 Buy
1474504 100mg $261.6 Buy
N1300000 n1300000 $220 Buy
N882000 5g $120 Buy
FN09246 25g $150 Buy

Narcotine Chemical Properties,Uses,Production

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]20D + 39.5° (H20); the phthalate, m.p. 160°C; [α]22D + 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

Antitussive.

Uses

antiacne, antiproliferative agent

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)

3860-46-6
128-62-1
Synthesis of Narcotine from (-)-β-Narcotine
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View Lastest Price from Narcotine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Narcotine pictures 2022-09-14 Narcotine
128-62-1
US $0.00-0.00 / kg 1kg 99% content 1000 Gansu Agricultural Reclamation Medical Alkaloids Factory Co., Ltd
Narcotine pictures 2020-01-18 Narcotine
128-62-1
US $3.00 / KG 1KG 98% 1kg , 5kg, 50kg Career Henan Chemical Co
  • Narcotine pictures
  • Narcotine
    128-62-1
  • US $0.00-0.00 / kg
  • 99% content
  • Gansu Agricultural Reclamation Medical Alkaloids Factory Co., Ltd
  • Narcotine pictures
  • Narcotine
    128-62-1
  • US $3.00 / KG
  • 98%
  • Career Henan Chemical Co
Capval Coscopin Coscotabs dl-Narcotine [dl-form] Gnoscopine [dl-form] Hederix (free base) Key-Tusscapine l-alpha-2-methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1 l-alpha-noscapine Longatin Lyobex Methoxyhydrastine Narcompren Narcosine Narcotin Narcotussin Narkotin Nectadon Nicolane Nipaxon Noscapal Noscapalin Noscapin NSC 5366 l-a-Narcotine L-a-Noscapine Longactin Narcotine (7CI, 8CI) Detusso Ecasil Terial Noscapine (base and/or unspecified salts) (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-γ],isoquinolin-5-yl]-1(3H)-isobenzofuranone 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-isobenzofuranone, [S-(R*,S*)] L-α-Narcotin Noscapine (500 mg) Noscapine (Narcotine) base Noscapine (100 mg) L-α-Noscapine ,2,3,4-tetrahydroisoquinaline [S-(R*,S*)]-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-Isobenzofuranone 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]- 1-alpha-Narcotine 5-g)isoquinolin-5-yl)-,(s-(r*,s*))-3-dioxolo(4 5-g]isoquinolin-5-yl)-,[s-(theta,s)]-3-dioxolo[4 6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one nsc5366 O-Methylnarcotoline Opian Opianin Opianine Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)- Terbenol Tusscapine tusseapine Vadebex (-)-a-Narcotine (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone