Gnoscopine
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Gnoscopine
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CAS No:
6035-40-1
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Formula:
C22H23NO7
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Chemical Name:
Gnoscopine
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Synonyms:
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)-rel-;Narcotine,(±)-;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)-,(R*,S*)-(±)-;1,3-Dioxolo[4,5-g]isoquinoline,1(3H)-isobenzofuranone deriv.;rel-(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;Gnoscopine;α-Gnoscopine;(±)-α-Narcotine;dl-Narcotine;(±)-Noscapine;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)-,(R*,S*)-;NSC 96350
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CAS No:
Description
Solid
(-)-noscapine is 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 plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects. It has a role as an antitussive, an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is a benzylisoquinoline alkaloid, a tertiary amino compound, a cyclic acetal, an isobenzofuranone, an organic heterobicyclic compound, an organic heterotricyclic compound and an aromatic ether. It derives from a (-)-noscapine hemiacetal.|Noscapine is a phthalide isoquinoline non-narcotic alkaloid derived from the opium poppy Papaver somniferum, with mild analgesic, antitussive, and potential antineoplastic activities. Noscapine exerts its antitussive effects through the activation of sigma opioid receptors. This agent appears to exert its antimitotic effect by binding to tubulin, resulting in a disruption of microtubule assembly dynamics and subsequently, the inhibition of mitosis and tumor cell death.|A naturally occurring opium alkaloid that is a centrally acting antitussive agent.
Gnoscopine Basic Attributes
413.42100
413.42
204-899-2
8V32U4AOQU
121869|5366
DTXSID4023385
C80589
ORTHORHOMBIC BISPHENOIDAL PRISMS|FINE, WHITE, OR PRACTICALLY WHITE, CRYSTALLINE POWDER
R - Respiratory system
Characteristics
75.69000
2.81970
1.332g/cm3
176 °C
565.3ºC
295.7ºC
1.602
4.49e-04 M|PKA 6.24; FREELY SOL IN ETHANOL; INSOL IN DIETHYL ETHER /HYDROCHLORIDE/|FINE, WHITE, OR PRACTICALLY WHITE, CRYSTALLINE POWDER; ODORLESS OR HAS SLIGHT ODOR OF ETHANOL; FREELY SOL IN CHLOROFORM & METHANOL; SOL IN ALCOHOL; SPARINGLY SOL IN ACETONE; PRACTICALLY INSOL IN ETHER; SOLN IN WATER IS DEXTROROTATORY; PH OF SOLN (1 IN 20) BETWEEN 2.5 & 3.5 /HYDROCHLORIDE/|HEMIHYDRATE TO TETRAHYDRATE, CRYSTALS; VERY SOL IN WATER /HYDROCHLORIDE/|CRYSTALS; FREELY SOL IN WATER; SOL IN METHANOL, ETHANOL; SLIGHTLY SOL IN ETHYL ACETATE; PRACTICALLY INSOL IN ETHER /CAMPHORSULFONATE/|PRACTICALLY INSOL IN VEGETABLE OILS; SLIGHTLY SOL IN NH4OH, HOT SOLN OF KOH & NAOH|SLIGHTLY SOL IN ALCOHOL & ETHER|INSOL IN WATER; SOL IN BENZENE & ACETONE|0.3 mg/mL at 30 °C
ODORLESS
VERY BITTER TASTE
PK 7.8; KB 1.5X10-8
194.3 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]|195.2 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated]
SALTS FORMED WITH ACIDS ARE DEXTROROTATORY|ITS SOLN IN CHLOROFORM IS LEVOROTATORY
Safety Information
SUBLIMES @ 150-160 °C|VERY WEAK BASE FORMING UNSTABLE SALTS WITH ACIDS & STRONG BASES; SALTS FORMED WITH ACIDS ARE UNSTABLE IN WATER|STABLE IN LIGHT & AIR
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 200 companies from 3 notifications to the ECHA C&L Inventory.|H302: Harmful if swallowed [Warning Acute toxicity, oral]
Toxicity
...NATURALLY OCCURRING OPIUM ALKALOID OF BENZYLISOQUINOLINE GROUP...|...NATURALLY OCCURRING (LEVO-FORM) OF ALKALOID NARCOTINE. ... ISOLATED FROM OPIUM IN WHICH IT IS PRESENT IN AMT RANGING FROM 3-10%.
Drug Information
Investigated for use/treatment in lymphoma (non-hodgkin's), leukemia (lymphoid), cancer/tumors (unspecified), and multiple myeloma.
Antitussive Agents|ANTITUSSIVE AGENT WHICH DEPRESSES MEDULLARY CENTERS & SUPPRESSES COUGH REFLEX. IT IS USED IN MGMNT OF COUGH IN BRONCHIAL ASTHMA & PULMONARY EMPHYSEMA. DRUG REDUCES FREQUENCY & INTENSITY OF COUGHING PAROXYSMS.|DRUG HAS NO MORPHINE-LIKE EFFECTS & HAS NO EFFECT ON MORPHNE ABSTINENCE SYNDROME. TOLERANCE TO ANTITUSSIVE EFFECT HAS NOT BEEN OBSERVED. NOSCAPINE IS NO LONGER CONTROLLED UNDER FEDERAL NARCOTIC LAW.|NOSCAPINE HAS NO ANALGESIC PROPERTIES OR DEPENDENCE LIABILITY.|NOSCAPINE HAD NO ANTITUSSIVE ACTIVITY IN VOLUNTEERS.
THERAPEUTICALLY EFFECTIVE DOSES ARE ESSENTIALLY DEVOID OF UNPLEASANT SIDE EFFECTS OF CODEINE &, EXCEPT FOR OCCASIONAL NAUSEA, ITS SIDE EFFECTS ARE NEGLIGIBLE. DOSES UP TO 90 MG HAVE NO EFFECT ON RESPIRATION IN MAN.|SIDE EFFECTS, PREDOMINANTLY GI, ARE SEEN IN UP TO 30% OF PT STUDIED.|Maternal Medication usually Compatible with Breast-Feeding: Noscapine: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/
Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)
ITS ANTITUSSIVE POTENCY & ONSET & DURATION OF ACTION ARE APPROX EQUAL, MG FOR MG, TO THOSE OF CODEINE.
MECONIN WAS THE MAJOR URINARY METABOLITE OF RATS, RABBITS, & HUMANS WHO HAD RECEIVED 120, 150 MG/KG & 10 MG, RESPECTIVELY, ORALLY. IT ACCOUNTED FOR APPROX 3, 8, & 2% OF DOSE RESPECTIVELY, AFTER 24 HR. O-DEMETHYLATED METABOLITES WERE ALSO FOUND.
Noscapine's antitussive effects appear to be primarily mediated by its sigma receptor agonist activity. Evidence for this mechanism is suggested by experimental evidence in rats. Pretreatment with rimcazole, a sigma specific antagonist, causes a dose-dependent reduction in antitussive activity of noscapine.|...EXCEPT FOR ITS ANTITUSSIVE EFFECT, IT HAS NO SIGNIFICANT ACTIONS ON CNS IN DOSES WITHIN THERAPEUTIC RANGE.
ADVERSE REACTIONS OCCUR INFREQUENTLY & INCL DROWSINESS, HEADACHE, NAUSEA, NONSEASONAL ALLERGIC (VASOMOTOR) RHINITIS, & CONJUNCTIVITIS.
Capval
Gnoscopine Use and Manufacturing
MAILLARD, US PATENT 3,108,106 (1963 TO JACQUES LOGEAIS).
TUSSCAPINE (FISONS). ORAL: LIQUID 15 MG/5 ML
OPIUM ALKALOID, ISOLATED FROM PLANT PAPAVER SOMNIFERUM L PAPAVERACEAE. FIRST ISOLATION: ROBIQUET, ANN CHIM PHYS (2) 5, 275 (1817). EXTRACTABLE FROM WATER INSOLUBLE RESIDUE REMAINING FROM PROCESSING OF OPIUM FOR MANUFACTURE OF MORPHINE.
A RAPID & ACCURATE PROTON MAGNETIC RESONANCE (PMR) PROCEDURE REPORTED.
Pharmaceuticals
Computed Properties
Molecular Weight:413.4
XLogP3:2.7
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:413.14745207
Monoisotopic Mass:413.14745207
Topological Polar Surface Area:75.7
Heavy Atom Count:30
Complexity:647
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes