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

• ChemBase ID: 1096
• Molecular Formular: C23H31NO2
• Molecular Mass: 353.49774
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate
• IUPAC Traditional name: levomethadyl acetate
• Brand Name: Orlaam
• Synonyms: 1-alpha-acetylmethadol; LAAM; Levacetilmetadol [INN-Spanish]; Levacetylmethadol; Levacetylmethadolum [INN-Latin]; Levo-Alphacetylmethadol; Levo-Methadyl Acetate; Levomethadyl; Nor-LAAM; Levomethadyl Acetate

Database IDs

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

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4385403
• LogD (pH = 7.4): 2.4523962
• Log P: 4.8847694
• Molar Refractivity: 117.8576 cm^3
• Polarizability: 42.51397 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.78
• LOG S: -5.3
• Solubility (Water): 1.79e-03 g/l

PROPERTIES

Physical Property

• Solubility: >15 mg/mL
• Hydrophobicity(logP): 5.4

DETAILS

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