Sinomenine

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Danger

• 유해·위험 문구

  H302：삼키면 유해함

  H315：피부에 자극을 일으킴

  H319：눈에 심한 자극을 일으킴

  H335：호흡 자극성을 일으킬 수 있음

  H351：암을 일으킬 것으로 의심됨 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재)

  H372：장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴

• 예방조치문구

  P201：사용 전 취급 설명서를 확보하시오.

  P302+P352：피부에 묻으면 다량의 물로 씻으시오.

  P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

  P308+P313：노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.

Sinomenine MSDS

• (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one

Sinomenine 화학적 특성, 용도, 생산

• 개요

  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.

• 물리적 성질

  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.

• 역사

  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.

• 용도

  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.

• 생물학적 활성

  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 .

• 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.]

• 참고 문헌

  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)

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