(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate

• ChemBase编号: 1096
• 分子式: C23H31NO2
• 平均质量: 353.49774
• 单一同位素质量: 353.23547924
• SMILES: O([C@H](C(C[C@@H](N(C)C)C)(c1ccccc1)c1ccccc1)CC)C(=O)C
• Canonical SMILES: CC[C@@H](C(c1ccccc1)(c1ccccc1)C[C@@H](N(C)C)C)OC(=O)C
• InChI: InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1
• InChIKey: XBMIVRRWGCYBTQ-AVRDEDQJSA-N

名称和登记号

名称

• IUPAC标准名: (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate
• IUPAC传统名: levomethadyl acetate
• 商标名: Orlaam
• 别名: 1-alpha-acetylmethadol; LAAM; Levacetilmetadol [INN-Spanish]; Levacetylmethadol; Levacetylmethadolum [INN-Latin]; Levo-Alphacetylmethadol; Levo-Methadyl Acetate; Levomethadyl; Nor-LAAM; Levomethadyl Acetate

登记号

• CAS号: 1477-40-3
• PubChem SID: 160964559; 46507749
• PubChem CID: 15130

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.4385403
• LogD (pH = 7.4): 2.4523962
• Log P: 4.8847694
• 摩尔折射率: 117.8576 cm^3
• 极化性: 42.51397 Å^3
• 极化表面积: 29.54 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.78
• LOG S: -5.3
• 溶解度: 1.79e-03 g/l

分子性质

理化性质

• 溶解度: >15 mg/mL
• 疏水性(logP): 5.4

详细说明

DrugBank - DB01227

• Drug Groups: approved
• Description: A narcotic analgesic with a long onset and duration of action. It is used mainly in the treatment of narcotic dependence. [PubChem]
• Indication: For the treatment and management of opiate dependence. It is sometimes used to treat severe pain in terminal patients.
• Pharmacology: Levomethadyl acetate (also known as LAAM) is a synthetic synthetic opioid analgesic with multiple actions quantitatively similar to those as morphine, the most prominent of which involve the central nervous system and organs composed of smooth muscle. However, levomethadyl acetate is more active and more toxic than morphine. The principal actions of therapeutic value are analgesia and sedation and detoxification or temporary maintenance in narcotic addiction. In this respect, the drug is similar to Methadone and also has structural similarities to it. The levomethadyl acetate abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, the course is more prolonged, and the symptoms are less severe.
• Toxicity: Signs of overdose include apnea, circulatory collapse, pulmonary edema, cardiac arrest, and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Levomethadyl acetate undergoes extensive first-pass metabolism to the active demethylated metabolite nor-levomethadyl acetate, which is further demethylated to a second active metabolite, dinor-levomethadyl acetate. These metabolites are more potent than the parent drug.
• Absorption: Levomethadyl acetate is rapidly absorbed from an oral solution.
• Half Life: 2.6 days
• Protein Binding: Approximately 80%
• External Links: Wikipedia; RxList; Drugs.com