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Sinomenine

Product Name
Sinomenine
CAS No.
115-53-7
Chemical Name
Sinomenine
Synonyms
CUCOLINE;(4bR,8aS,9S)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one;SNM;COCULINE;KUKOLINE;SINOMENIN;SabiaineA;SINOMENINE;SABIANINE A;Sinomenine I
CBNumber
CB4399085
Molecular Formula
C19H23NO4
Formula Weight
329.39
MOL File
115-53-7.mol
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Sinomenine Property

Melting point:
180 °C (dec.)(lit.)
alpha 
D26 -71° (c = 2.1 in alc)
Boiling point:
466.98°C (rough estimate)
Density 
1.2012 (rough estimate)
refractive index 
1.5000 (estimate)
storage temp. 
Store at +4°C
solubility 
Soluble to 65 mg/mL (197.33 mM) in DMSO
form 
Solid
pka
9.72±0.40(Predicted)
color 
White to off-white
Merck 
13,8620
InChIKey
YMEVIMJAUHZFMW-VUIDNZEBSA-N
LogP
1.245 (est)
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Safety

Hazard Codes 
T,Xn
Risk Statements 
45-46-23/24/25-36/37/38-20/21/22-48/20/22-40-22-63
Safety Statements 
53-22-26-36/37/39-45-36/37-24/25
RIDADR 
1544
WGK Germany 
3
RTECS 
QD2170000
F 
9
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29399990
Toxicity
LD50 orally in mice: 580 mg/kg (Fu)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H351Suspected of causing cancer

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P201Obtain special instructions before use.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001208
Product name
Sinomenine
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0001208
Price
$164
Updated
2024/03/01
Sigma-Aldrich
Product number
365602
Product name
Sinomenine
Purity
0.3mol chloroform of crystallization
Packaging
100mg
Price
$70
Updated
2023/06/20
ApexBio Technology
Product number
N1722
Product name
Sinomenine
Packaging
20mg
Price
$40
Updated
2021/12/16
Biosynth Carbosynth
Product number
FS09811
Product name
Sinomenine
Packaging
250mg
Price
$52.5
Updated
2021/12/16
Biosynth Carbosynth
Product number
FS09811
Product name
Sinomenine
Packaging
500mg
Price
$80
Updated
2021/12/16
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Sinomenine Chemical Properties,Usage,Production

Description

Isolated by Ohta from Cocculus diversifolius DC., this alkaloid forms colourless crystals from MeOH. It is stated to possess a powerful reflex action and to be aspasm stimulant, finally causing paralysis and death in toxic doses. It is also said to suppress the hypotensive action of dihydroxyphenylethanolethylamine.

Physical properties

Appearance: acicular crystals (crystallized from benzene). Solubility: soluble in ethanol, acetone, chloroform, and dilute alkali; slightly soluble in water, ether, and benzene. Melting point: 219–221?°C. Specific optical rotation:?– 71° (c?=?2.1, ethanol). Its hydrochloride, crystallization (water or ethanol), decomposed at 278?°C.?Its hydroiodide, needle crystal (crystallized from water), decomposed at 272?°C.?Its picrate, which is yellow needle crystal, decomposed at 176?°C.?Sinomenine is sensitive to light and heat to decompose.

History

The chemical structure of sinomenine is composed of four rings, A, B, C, and D, similar to the structure of morphine. Ring A is a benzene ring, and ring B is a half-chair-shaped, six-member ring. The C ring is a twisted-chair-type, sixmember ring that has an a, β-unsaturated ketone structure attached to the B ring. The D ring is a nitrogen-containing, sixmember ring under the B ring. Its structure is shown below; the current structural modification of sinomenine is mainly focused on the A/C active group.
Based on the transformation of the A ring, it was found that the 1-substituted formyl derivative of sinomenine showed the strongest inhibitory effect on the inflammatory response of the mouse ear. The 4-substituted p-chlorobenzoyl-sinomenine has the strongest anti-inflammatory and analgesic activity. The biotransformation and chemical synthesis were also used to prepare the di-sinomenine derivatives linked by carbon and carbon, which was stronger than that of sinomenine and had a strong inhibitory effect on cell inflammatory factors. Sinomenine derivatives of the C ring with a pyrazine ring have a strong inhibitory effect on T, B lymphocyte proliferation reaction, which can be used for the preparation of immunomodulatory drugs. The transformation of C ring carbonyl yielded a series of shift alkali derivatives, with strong anti-inflammatory and analgesic effects. These attempts are important for the development of new drugs.

Uses

weak abortifacient, immunosuppressant, analgesic, antiinflammatory; LD50 (po) 580 mg/kg; (ip) 285 mg/kg(mouse)

Indications

It is mainly used for the treatment of rheumatoid arthritis and other types of rheumatism and arrhythmia in clinical.

Definition

ChEBI: Sinomenine is a morphinane alkaloid.

Biological Activity

Natural anti-inflammatory morphinan analog. Causes degranulation of mast cells in mammalian tissues to release histamine and suppresses production of proinflammatory cytokines. Also displays antinociceptive activity, possibly through activation of the μ -opioid receptor. Stimulates short-term renewal of human embryonic stem cells (ESCs) in vitro .

Pharmacology

Sinomenine has anti-inflammatory, immunosuppressive, analgesic sedation, antiarrhythmic, detoxification, and other pharmacological effects, while the half-life of sinomenine is short. In addition, sinomenine also causes a strong histamine release, which leads to rash, gastrointestinal reactions, and other side effects, limiting its wide range of clinical applications.
1. Effects on central nervous system
(a) Analgesic effect: The chemical structure of sinomenine and morphine are similar (Fig.?3). They both act on the central nervous system with a significant analgesic effect, but the mechanisms are different. It has been shown that the analgesic effect of sinomenine has nothing to do with the release of histamine.
(b) Sedative effect: Sinomenine has an inhibitory effect on the central nervous system. The sedative effect works by inhibiting the excitement of advanced neurological activity. Sinomenine can also eliminate the “anger” response of mice caused by electrical stimulation, showing a stabilizing effect. In addition, although, like morphine, it had mainly a sedative effect on the central nervous system, sinomenine also has some excitatory effects on some parts of the central nervous system, especially the spinal cord.
Other effects on the central nervous system: Sinomenine may, to a slight degree, induce vomiting. Sinomenine also has local anesthetic effects on frog nerve endings and rabbit cornea that could be applied for local infiltration anesthesia.
2. Effects on peripheral nervous system
Sinomenine can reversibly block the neuromuscular transmission, which showed a concentration-dependent inhibitory effect. Sinomenine had no significant effect on nerve stem excitability and conductivity.
3. Impact on cardiovascular system
Sinomenine has a significant antihypertensive effect. Sinomenine also has a significant antagonistic effect on ischemic arrhythmia.
4. Anti-inflammatory and antiallergic effects
The anti-inflammatory effect of sinomenine is significant.

Clinical Use

The treatment of rheumatism and rheumatoid arthritis is one of the most important clinical applications of sinomenine. Sinomenine is particularly suitable for the treatment of arrhythmia caused by organic heart disease. Sinomenine is used for the treatment of glomerular disease, which can reduce urinary protein and relieve hematuria symptoms, and the side effects were significantly lower than that of tripterygium glycoside tablets, which are commonly used in clinical practice. In addition, sinomenine can significantly inhibit renal interstitial fibrosis and the production of tissue growth and growth factor TGF-β1. Sinomenine can significantly delay the development of chronic renal failure and effectively treat ankylosing spondylitis.

Purification Methods

Crystallise the salt from water (1g/1.5mL) or EtOH. The free base [115-53-7] M 329.4, has m 161o (from EtOH) (and again at 182o) after crystallisation from *C6H6, and [] D -78.9o (c 1, EtOH). The picrate has m 159-162o(dec) (from H2O). [Beilstein 21 II 470, 21 III/IV 6670.]

References

Ohta., Ber. ges. Physiol., 33, 352 (1925)
Ohta, Kitasato., Arch. expo Med., 6, 259, 283 (1925)
Raymond-Hamet., Compt. rend. Soc. Biol., 125, 509 (1937)

Sinomenine Preparation Products And Raw materials

Raw materials

Preparation Products

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Sinomenine Suppliers

China 294 Germany 2 India 1 Japan 1 Slovakia 1 South Korea 1 Switzerland 2 United Kingdom 10 United States 31 USA 1 Global 344
AdooQ BioScience, LLC
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857-239-0968
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TargetMol Chemicals Inc.
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+1-781-999-5354 +1-00000000000
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marketing@targetmol.com
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Aladdin Scientific
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View Lastest Price from Sinomenine manufacturers

Changsha Staherb Natural Ingredients Co., Ltd.
Product
Sinomenine 115-53-7
Price
US $0.00/KG
Min. Order
1KG
Purity
≥98% HPLC
Supply Ability
1000KG
Release date
2022-09-22
Qingdao RENAS Polymer Material Co., Ltd.
Product
sinomenine 115-53-7
Price
US $0.00/kg
Min. Order
20kg
Purity
99%
Supply Ability
20 tons
Release date
2024-10-29
Shanghai Standard Technology Co., Ltd.
Product
Sinomenine 115-53-7
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2020-04-26

115-53-7, SinomenineRelated Search:

2,6-Dimethoxybenzaldehyde Diphenyldimethoxysilane 1,1-Dimethoxyethane Dimethylamine Dimethoxymethane Dimethyl carbonate Metformin Dimethyldimethoxysilane EC 1.1.1.28 CHLOROPHOSPHONAZO III (S)-(+)-1-METHYL-3-PHENYLPROPYLAMINE (R)-2-AMINOTETRALIN 4-METHYL-4-PHENYLPENTAN-2-ONE 6-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALENE 1,2-Cyclohexanedione 2,4-Dimethylpiperidine Sinomenine Stem P.E Oxygen

  • 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9-alpha,13-alpha,14-alpha-mo
  • 9-alpha,13-alpha,14-alpha-morphinan-6-one,7,8-didehydro-4-hydroxy-3,7-dimethox
  • rphinan-6-one
  • y-17-methyl-
  • SABIANINE A
  • SINOMENIN
  • SINOMENINE
  • (9alpha,13alpha,14alpha)-7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
  • Sinomenine 115-53-7
  • SabiaineA
  • Sinomenine I
  • (9Alpha,13alpha,14alpha)-4-hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochlo
  • Sinomenine (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
  • Sinomenine 0.3 mol chloroform of crystallization
  • (9alpha,13alpha,14alpha)-4-hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride
  • Sinomenine, >=98%
  • Sinomenine/Sinomenine Hydrochloride
  • (4bR,8aS,9S)-4-hydroxy-3,7-dimethoxy-11-methyl-9,10-dihydro-5H-9,4b-(epiminoethano)phenanthren-6(8aH)-one
  • Sinomenine, 98%, from Caulis Sinomenii
  • CUCOLINE
  • COCULINE
  • KUKOLINE
  • Sinomenine std.
  • Sinomenine SINOMENIN
  • SINOMENINE(RG)
  • Sinomenine hydrochorolide
  • Morphinan-6-one,7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-,(9α,13α,14α)-
  • Sinomenine，Coculine，Cucoline，Tuduranine
  • (9a,13a,14a)-7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
  • (9α,13α,14α)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one
  • SINGLIROXBRUGHROSEFRUITP.E
  • 9α,13α,14α-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-onehydrochloride
  • SNM
  • SinoMenine (Cucoline)
  • (+)-SinoMenine N-oxide
  • SinoMenine (6CI,7CI)
  • Sinomenine CRS
  • Sinomenine Standard
  • Sinomenine USP/EP/BP
  • Sinomenine hydrochlo
  • Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9α,13α,14α)-
  • Abametapir Impurity 25
  • 115-53-7
  • C19H23NO403CHCl3
  • C19H23NO4
  • Asymmetric Synthesis
  • Chiral Building Blocks
  • Complex Molecules
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • API
  • Asymmetric Synthesis
  • Chiral Building Blocks
  • Complex Molecules
  • Natural Plant Extract