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(-)-3-メトキシ-17-メチルモルフィナン

Levomethorphan

HCID 5362449
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
125-70-2
標準SMILES
COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C)CC3
InChIKey
MKXZASYAUGDDCJ-CGTJXYLNSA-N
分子式
C18H25NO
平均分子量
271.4 g/mol
単同位体質量
271.19361442

概要

Levomethorphan is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the stereocenters at positions 4a, 10 and 10a have R-configuration. It is a prodrug of levorphanol and a strong narcotic analgesic, and listed as a schedule II controlled substance. It has a role as an opioid analgesic and a prodrug. It is functionally related to a Levorphanol. It is an enantiomer of a dextromethorphan.

名称と識別子

優先名称
Levomethorphan
IUPAC
(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
現地名
(-)-3-メトキシ-17-メチルモルフィナン
英語名
levomethorphan
分子式
C18H25NO
分子量
271.4

名称と別名

Levomethorphanl-MethorphanLevomethorphaneLevometorfanoLevomethorphanum125-70-2(-)-3-Methoxy-N-methylmorphinan7ZZ22K9QE6IDS-NL-004IDS-NL-005CHEBI:146176DTXSID20872403
名称をさらに表示
(9β,13β,14β)-3-メトキシ-17-メチルモルフィナン(-)-3-メトキシ-17-メチルモルフィナンレボメトルファン3-メトキシ-17-メチルモルフィナンl-メトルファン(1R,9R,10R)-4-メトキシ-17-メチル-17-アザテトラシクロ[7.5.3.01,10.02,7]ヘプタデカ-2,4,6-トリエンDextromethorphan Impurity 18 HClDextromethorphan reference substance ELevomethorphan (1.0mg/ml in Acetonitrile)Morphinan, 3-methoxy-17-methyl- (8CI, 9CI)Dextromethorphan Impurity 6(Levomethorphan)Levomethorphan (dextromethorphan impurity 23)Levomethorphan (Dextromethorphan EP Impurity E)2H-10,4a-Iminoethanophenanthrene, 1,3,4,9,10,10a-hexahydro-6-methoxy-11-methyl- (6CI)
RefChem:924704DTXCID00820048204-751-7Methorphan3-Methoxy-17-methylmorphinanLevometorfano [INN-Spanish]Levomethorphane [INN-French]Levomethorphanum [INN-Latin]

物性

構造計算による物性

XLogP
3.4
極性表面積
12.5 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
1
重原子数
20
形式電荷
0
複雑度
370

実験および物理化学的性質

Drugs · 4 件

DEA NFLIS-Drug Category -> Narcotic Analgesics

DEA NFLIS-Drug Category -> Narcotic Analgesics

DEA Schedule II Controlled Substance -> Opiates

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP3.6
Solubility8.51 mg/L
Physical DescriptionSolid

物理化学的性質

貯蔵温度
2 · 2-8°C
溶解性
Chloroform (Slightly), Ethanol (Slightly), Methanol (Sparingly)
沸点
394.9 · 394.9±42.0 °C(Predicted)
比重(密度)
1.11 · 1.11±0.1 g/cm3(Predicted)
融点
81 · 81-83 °C
酸解離定数(Pka)
9.13 · 9.13±0.20(Predicted)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H302 (97.5%): 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 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationDEA schedule II controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (97.5%)

毒性情報

Health EffectsHypertension, shallow respiration. Dextromethorphan can cause other gastrointestinal disturbances. [Wikipedia]
Exposure RoutesOral, rapidly absorbed from the gastrointestinal tract.
Toxicity Summary · 1 件

Dextromethorphan is an opioid-like drug that binds to and acts as antagonist to the NMDA glutamatergic receptor, it is an agonist to the opioid sigma 1 and sigma 2 receptors, it is also an alpha3/beta4 nicotinic receptor antagonist and targets the serotonin reuptake pump. Dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan.

Signs and Symptomssymptoms include vomitting, drowiness, diarrhea, urinary retention, fever, and sweating. [Wikipedia]
Carcinogen Classification

化学と産業

薬理情報

Metabolism/MetabolitesHepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. Half Life: 3-6 hours
MeSH Pharmacological Classification · 2 件

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.

Cellular LocationsMembrane

用途と製造

Uses · 2 件

Use (kg; approx.) in Germany (2009): >1000

The primary use of dextromethorphan is as a cough suppressant, for the temporary relief of cough caused by minor throat and bronchial irritation (as commonly accompanies the common cold), as well as those resulting from inhaled irritants. In addition, a combination of dextromethorphan and quinidine has been shown to alleviate symptoms of easy laughing and crying (pseudobulbar affect) in patients with amyotrophic lateral sclerosis and multiple sclerosis.

応用分野

使用The enatiomer of Dextromethorphan (D299455), an antitussive medicine, a narcotic.

関連反応

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化合物ノート

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データベース識別子

CAS
125-70-2、125-71-3、510-53-2
PubChem CID
5362449
DTXSID
DTXSID20872403
ChEMBL
CHEMBL1908323
ChEBI
CHEBI:146176
UNII
7ZZ22K9QE6、8YB8F78WM1
EC Number
204-751-7
Nikkaji
J9.355F
No indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 165 mg/kg (mice) (L1858) LD50: 350 mg/kg (rat) (L1858)

安全データ

wgk
3
毒性
mouse,LD50,subcutaneous,78mg/kg (78mg/kg),British Journal of Pharmacology and Chemotherapy. Vol. 17, Pg. 433, 1961.
hs_code
2933492250
risk_code
22
hazard_code
Xn