ChemicalBook > CAS DataBase List > Narcotine

Narcotine

Product Name
Narcotine
CAS No.
128-62-1
Chemical Name
Narcotine
Synonyms
Opian;Vadebe;Capval;Lyobex;Ecasil;Terial;Opianin;nsc5366;Vadebex;Nipaxon
CBNumber
CB8468501
Molecular Formula
C22H23NO7
Formula Weight
413.42
MOL File
128-62-1.mol
More
Less

Narcotine Property

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)
More
Less

Safety

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
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H336May cause drowsiness or dizziness

More
Less

N-Bromosuccinimide Price

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

Narcotine Chemical Properties,Usage,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

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)

Narcotine Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Narcotine Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
Advantage
65
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
meilunui@163.com
Country
China
ProdList
4727
Advantage
58
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9461
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
More
Less

View Lastest Price from Narcotine manufacturers

Career Henan Chemical Co
Product
Narcotine 128-62-1
Price
US $3.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg , 5kg, 50kg
Release date
2020-01-17

128-62-1, NarcotineRelated Search:


  • ,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
  • a-Narcotine
  • Vadebe
  • 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)- (9CI)
  • 1,3-Dioxolo[4,5-g]isoquinoline, 1(3H)-isobenzofuranone deriv.
  • L-ALPHA-NARCOTINE
  • 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
  • (S,R)-NOSCAPINE
  • (S)-6,7-DIMETHOXY-3-((R)-4-METHOXY-6-METHYL-5,6,7,8-TETRAHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-5-YL)-3H-ISOBENZOFURAN-1-ONE
  • NOSCAPINE
  • NARCOTINE
  • NOSCAPINE (NARCOTINE) NATURALLY OCCURRIN G O
  • 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1(3h)-isobenzofuranon
  • alpha-Narcotine
  • 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