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Sinomenine

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Name

Sinomenine

EINECS 204-094-6
CAS No. 115-53-7 Density 1.3 g/cm3
PSA 59.00000 LogP 1.95600
Solubility N/A Melting Point 180 °C (dec.)(lit.)
Formula C19H23NO4 Boiling Point 513.6 °C at 760 mmHg
Molecular Weight 329.396 Flash Point 264.4 °C
Transport Information N/A Appearance white powder
Safety 53-22-26-36/37/39-45 Risk Codes 45-46-23/24/25-36/37/38
Molecular Structure Molecular Structure of 115-53-7 (Sinomenine) Hazard Symbols ToxicT
Synonyms

7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one;BRN 0095280;CCRIS 1550;Coculine;Cucoline;Kukoline;Sabianine A;Sinomenine;

Article Data 7

Sinomenine Synthetic route

1246560-79-1

C22H27NO5

115-53-7

sinomenine

Conditions
ConditionsYield
With Aliquat 336; potassium hydroxide In water at 60℃; for 2h;99%
22610-64-6

4-acetyl-sinomenine

115-53-7

sinomenine

Conditions
ConditionsYield
With Aliquat 336; potassium hydroxide In water at 60℃; for 1h;99%
6080-33-7, 61487-22-7, 70617-35-5

Sinomenine Hydrochloride

115-53-7

sinomenine

Conditions
ConditionsYield
With ammonium hydroxide94%
With ammonium hydroxide94%
1000026-77-6

sinomenine N-oxide

115-53-7

sinomenine

Conditions
ConditionsYield
With FAD; NADH In aq. phosphate buffer at 37℃; for 2h; Reagent/catalyst;
115-53-7

sinomenine

6106-71-4

(Z,E)-sinomenine oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; Aliquat 336 In water at 60℃; for 1h;99%
With hydroxylamine hydrochloride; sodium acetate In methanol at 80℃; for 15h;99%
With hydroxylamine hydrochloride; sodium acetate In ethanol for 8h; Reflux;95%
64-17-5

ethanol

115-53-7

sinomenine

1246560-80-4

4-O-ethylsinomenine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 12.5h; Mitsunobu reaction;99%
111-83-1

1-bromo-octane

115-53-7

sinomenine

1372785-17-5

4-O-(n-octyl)sinomenine

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃;99%
115-53-7

sinomenine

1000026-77-6

sinomenine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 24h;98.7%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.5h;76%
With dihydrogen peroxide for 72h; Inert atmosphere;60%
With dihydrogen peroxide for 48h;
With dihydrogen peroxide at 20℃; for 60h;
693-58-3

1-Bromononane

115-53-7

sinomenine

1351932-96-1

4-O-(n-nonyl)sinomenine

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃;98%
106-94-5

propyl bromide

115-53-7

sinomenine

1372785-14-2

4-O-(n-propyl)sinomenine

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃;98%

Sinomenine Specification

The Sinomenine, with the CAS registry number 115-53-7, is also known as 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-morphinan-6-one. It belongs to the product categories of Alkaloids; Natural Plant Extract; Asymmetric Synthesis; Chiral Building Blocks; Complex Molecules. Its EINECS registry number is 204-094-6. This chemical's molecular formula is C19H23NO4 and molecular weight is 329.39022. Its systematic name is called (9alpha,13alpha,14alpha)-4-hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one. It is traditionally used in herbal medicine in these countries, as a treatment for rheumatism and arthritis. This chemical's classification code is Drug / Therapeutic Agent.

Physical properties of Sinomenine: (1)ACD/LogP: 1.83; (2)ACD/LogD (pH 5.5): -1; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 2; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 51; (8)#H bond acceptors: 5; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.625; (12)Molar Refractivity: 89.463 cm3; (13)Molar Volume: 253.14 cm3; (14)Surface Tension: 57.131 dyne/cm; (15)Density: 1.301 g/cm3; (16)Flash Point: 264.442 °C; (17)Enthalpy of Vaporization: 81.476 kJ/mol; (18)Boiling Point: 513.643 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical that at low levels can cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. In addition, it is toxic by inhalation, in contact with skin and if swallowed. This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: CO/C3=C/[C@@H]4[C@@H]2Cc1ccc(OC)c(O)c1[C@]4(CCN2C)CC3=O
(2)InChI: InChI=1/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
(3)InChIKey: INYYVPJSBIVGPH-QHRIQVFBBL

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 285mg/kg (285mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 8, Pg. 177, 1960.
mouse LD50 oral 580mg/kg (580mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 10, Pg. 673, 1963.

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