Noscapine (HCID 275196)

이름 및 식별자

우선 이름: Noscapine
IUPAC: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
현지명: 노스카빈
영어명: Narcotine
분자식: C22H23NO7
분자량: 413.42

이름 및 동의어

noscapine128-62-1NARCOTINETusscapineMethoxyhydrastineTerbenolCoscopinNarcomprenNarcosineVadebexNoscapalinLongatin

이름 더 보기

노스카빈노스카핀노스카핀및그염류OpianVadebeCapvalEcasilTerialOpianinnsc5366

Opianine(-)-NarcotineNarcotinNarcotussinNectadonNicolaneNoscapinLyobex

데이터베이스 식별자

CAS: 128-62-1、6035-40-1
PubChem CID: 275196
ChEMBL: CHEMBL364713
ChEBI: CHEBI:73237
UNII: 8V32U4AOQU、A4C6WE7BZN
EC Number: 204-899-2
Nikkaji: J9.283E

물성

구조 계산 물성

XLogP: 2.7
극성 표면적: 75.7 Å²
수소 결합 공여자 수: 0
수소 결합 수용자 수: 8
회전 가능 결합 수: 4
무거운 원자 수: 30
형식 전하: 0
복잡도: 647

실험 및 물리화학적 성질

pHNEUTRAL TO LITMUS

OdorODORLESS

TasteVERY BITTER TASTE

Density1.395

Color/Form · 2건

ORTHORHOMBIC BISPHENOIDAL PRISMS

FINE, WHITE, OR PRACTICALLY WHITE, CRYSTALLINE POWDER

Solubility · 6건

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

물리화학적 성질

녹는점: 174 · 174-176 °C(lit.)
끓는 점: 532.6 °C · 532.6°C (rough estimate)
밀도: 1.395 · 1.395
굴절률: 1.5614 · 1.5614 (estimate)
저장 조건: -20 °C · -20°C Freezer, Under Inert Atmosphere
용해도: 물에는 거의 녹지 않으며, 아세톤에는 녹고, 에탄올에는 약간 녹습니다(96%). 강산에 용해됩니다. 용액을 물로 희석하면 염기가 침전될 수 있습니다.
산도 계수 (pKa): 7.8 · 7.8(at 25℃)
물리적 상태: Solid
색상: 에탄올로부터 침전된 사방정계 프리즘 결정
수용성: 302.9 mg/L · 302.9mg/L(25 ºC)
Merck: 13 · 13,6752
NIST: Narcotine alkaloid(128-62-1)
EPA: 1 · 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)

화학적 성질

Crystalline Solid

안전 및 규제

GHS 분류

GHS Classification · 6건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 140 reports by companies from 4 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 2건

Chemical: 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*)]-

Status: Active Update: 29-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19776

Other Safety Information · 1건

IMAP assessments - 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*)]-: Environment tier I assessment；IMAP assessments - 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*)]-: Human health tier I assessment

Hazard Classes and Categories · 2건

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

독성 정보

Natural Pollution Sources · 2건

...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%.

Human Toxicity ExcerptsADVERSE REACTIONS OCCUR INFREQUENTLY & INCL DROWSINESS, HEADACHE, NAUSEA, NONSEASONAL ALLERGIC (VASOMOTOR) RHINITIS, & CONJUNCTIVITIS.

Non-Human Toxicity ExcerptsIN DOGS, DRUG IS POTENT RELEASER OF HISTAMINE, & LARGE DOSES CAUSE BRONCHOCONSTRICTION & TRANSIENT HYPOTENSION. TOXIC DOSES PRODUCE CONVULSIONS IN ANIMALS.

규제 정보

Regulatory Information · 2건

Chemical: 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*)]-

Status: Active Update: 29-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19776

안전 데이터

wgk: 3
rtecs: RD2625000
ridadr: 1544
독성: cyt-ham:lng 100 mg/L ATSUDG (4),41,80
HS 번호: 29329990
risk_code: 22
hazard_code: Xn
safety_code: 24/25
포장분류: III
위험 등급: 6.1(b)
유해 물질 데이터: 128-62-1(Hazardous Substances Data)

화학 및 산업

약리 정보

ATC Code · 2건

R - Respiratory system；R05 - Cough and cold preparations；R05D - Cough suppressants, excl. combinations with expectorants；R05DA - Opium alkaloids and derivatives；R05DA07 - Noscapine

QR - Respiratory system；QR05 - Cough and cold preparations；QR05D - Cough suppressants, excl. combinations with expectorants；QR05DA - Opium alkaloids and derivatives；QR05DA07 - Noscapine

Mechanism of Action · 2건

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.

Metabolism/Metabolites · 1건

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.

MeSH Pharmacological ClassificationAgents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.

Absorption, Distribution and ExcretionITS ANTITUSSIVE POTENCY & ONSET & DURATION OF ACTION ARE APPROX EQUAL, MG FOR MG, TO THOSE OF CODEINE.

Cellular LocationsCytoplasm；Extracellular

용도 및 제조

Uses · 2건

MEDICATION

Use (kg; approx.) in Germany (2009): >1000；Consumption (g per capita; approx.) in Germany (2009): 0.0122；Excretion rate: 1；Calculated removal (%): 46.5

Methods of ManufacturingMAILLARD, US PATENT 3,108,106 (1963 TO JACQUES LOGEAIS).

Formulations/PreparationsTUSSCAPINE (FISONS). ORAL: LIQUID 15 MG/5 ML

Use ClassificationPharmaceuticals

General Manufacturing InformationOPIUM 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.

응용 분야 · 1건

개요A 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.

상·하류 제품 정보

상류 원료

(-)-β-나르코틴 7-O-DeMethylα-나르코틴

하류 제품

(3S)-3-[(5R)-9-amino-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one 코타르닌 [S-(R*,S*)]-3,4-dimethoxy-alpha1-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-o-xylene-alpha,alpha'-diol

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

추가 설명 · 1건

정의ChEBI: 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.