基本情報
- CAS
125-58-6- 標準SMILES
CCC(=O)C(C[C@@H](C)N(C)C)(c1ccccc1)c1ccccc1- InChIKey
USSIQXCVUWKGNF-QGZVFWFLSA-N- 分子式
- C21H27NO
- 平均分子量
- 309.4 g/mol
- 単同位体質量
- 309.20926449
概要
Levomethadone is a 6-(dimethylamino)-4,4-diphenylheptan-3-one that has (R)-configuration. It is the active enantiomer of methadone and its hydrochloride salt is used to treat adults who are addicted to drugs such as heroin and morphine. It has a role as an opioid analgesic, an antitussive, a mu-opioid receptor agonist and a NMDA receptor antagonist. It is an enantiomer of a dextromethadone.
名称と識別子
- 優先名称
- Levomethadone
- IUPAC
- (6R)-6-(dimethylamino)-4,4-diphenylheptan-3-one
- 現地名
- レボメタドン
- 英語名
- R(-)-methadone hydrochloride opioid agon IST
- 分子式
- C21H27NO
- 分子量
- 309.45
名称と別名
Levomethadonel-MethadoneLevothyl(-)-Methadonel-Polamivet(R)-Methadone(6R)-MethadoneLevometadonaLevadone125-58-6(6R)-6-(dimethylamino)-4,4-diphenylheptan-3-oneD-(-)-Methadone
名称をさらに表示
(6R)-6-(ジメチルアミノ)-4,4-ジフェニル-3-ヘプタノンレボメタドン(-)-アミドン(-)-ジアミノン(R)-(-)-メタドンl-メタドン[R,(-)]-6-ジメチルアミノ-4,4-ジフェニル-3-ヘプタノン(-)-メタドン(R)-6-ジメチルアミノ-4,4-ジフェニル-3-ヘプタノン(R)-メタドン(6R)-6-ジメチルアミノ-4,4-ジフェニル-3-ヘプタノン[R,(-)]-6-(ジメチルアミノ)-4,4-ジフェニル-3-ヘプタノン(R)-6-(ジメチルアミノ)-4,4-ジフェニル-3-ヘプタノンレボチルレボメサドンl-メサドン(6R)-6-(ジメチルアミノ)-4,4-ジフェニルヘプタン-3-オン(-)-DiaminoneLaevomethadon4-diphenyl-6-(dimethylamino)-l-3-heptanon4-diphenyl-6-(dimethylamino)-(r)-3-hetpanon
LevomethadonumR-(-)-MethadoneLevomethadone [INN]METHADONE, L-Levometadona [INN-Spanish]Levomethadonum [INN-Latin]6Y75Z4E8NS(R)-6-(Dimethylamino)-4,4-diphenyl-3-heptanone
物性
構造計算による物性
- XLogP
- 3.9
- 極性表面積
- 20.3 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
- 7
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 346
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
物理化学的性質
- 融点
- 99 °C · 99°C
- 沸点
- 449.71 °C · 449.71°C (rough estimate)
- 比重(密度)
- 1.035 · 1.0350 (rough estimate)
- 屈折率
- 1.5614 · 1.5614 (estimate)
- 酸解離定数(Pka)
- 9.048 · 9.048±0.50(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
Danger
H301 (95.1%): Toxic if swallowed [Danger Acute toxicity, oral]
P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationREACH registered substance: (6R)-6-(dimethylamino)-4,4-diphenylheptan-3-one (EC: 603-081-6)
Hazard Classes and CategoriesAcute Tox. 3 (95.1%)
安全データ
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H300
化学と産業
薬理情報
ATC Code
N - Nervous system
QN - Nervous system
用途と製造
UsesUse (kg) in Switzerland (2009): >75
Use ClassificationPharmaceuticals
調製方法
純化方法This pharmacologically active (against narcotic addiction) enantiomer was obtained by optical resolution (using D-tartaric acid) of the racemate and was purified by precipitation of the hydrochloride from aqueous solution at pH >6, dried and recrystallised from propan-2-ol. The R-hydrochloride [5967-73-7], when recrystallised from propan-2-ol, has m 245-246o, [] D 20 -169o (c 2, EtOH). The S-(+)-enantiomer [5653-8-5] also recrystallises from propan-2-ol and has recorded m of 100-101o, [] D 25 + 26o (c 1.2, H2O). The S-hydrochloride [15284-15-8], when crystallised from propan-2-ol, has m 243-244o, [] D 20 +169o (c 2, EtOH). [Larsen et al. J Am Chem Soc 70 4194 1948, Brode & Hill J Org Chem 13 191 1948, Schultz et al. J Am Chem Soc 69 2454 1947, Easton et al. J Am Chem Soc 69 2941 1947, Winter & Flataker J Pharmacol Exp Ther 98 305 1950, Beilstein 14 III 278, 1 4 III/IV 300.]
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