Structure via PubChem · Public domain (PubChem)
levomethadyl acetate
Sign in to saveAlso known as Levacetilmetadol, Levacetylmethadolum, levo-α-acetylmethadol, Levo-methadyl acetate, (1S,4S)-4-(dimethylamino)-1-ethyl-2,2-diphenylpentyl acetate, Orlaam®, (1S,4S)-4-(dimethylamino)-1-Ethyl-2,2-diphenylpentyl acetate
Levacetylmethadol (INN), levomethadyl acetate (USAN), OrLAAM (trade name) or levo-α-acetylmethadol (LAAM) is a synthetic opioid similar in structure to methadone. It has a long duration of action due to its active metabolites.
Chemical data
- Formula
- C23H31NO2
- Molecular weight
- 353.5 g/mol
- IUPAC name
- [(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl] acetate
- SMILES
- CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
- InChIKey
- XBMIVRRWGCYBTQ-AVRDEDQJSA-N
- XLogP
- 4.3
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1993
- Admin. routes
- oral
- Indications
- drug dependence, opioid dependence
via ChEMBL · EBI
Research
422 papers- A comparison of levomethadyl acetate, buprenorphine, and methadone for opioid dependence.The New England journal of medicine · 2000
- Torsades de pointes associated with high dose levomethadyl acetate (ORLAAM).Journal of addictive diseases · 2001
- Induction with levomethadyl acetate: safety and efficacy.Archives of general psychiatry · 1998
- Levomethadyl acetate. Prolonged duration of opioid effects, including cross tolerance to heroin, in man.JAMA · 1973
- Dose-related efficacy of levomethadyl acetate for treatment of opioid dependence. A randomized clinical trial.JAMA · 1997
via PubMed
Wikidata facts
- Subclass of
- methadyl acetate
- Mass
- 353.235479
- Has use
- medication
Show 6 more facts
- stereoisomer of
- alphacetylmethadol
- chemical formula
- C₂₃H₃₁NO₂
- canonical SMILES
- CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
- isomeric SMILES
- CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
- World Health Organisation international non-proprietary name
- levacetylmethadol
- subject has role
- opioid
Sources (5)
via Wikidata · CC0
~3 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Legal status
- References
- Further reading
- External links
Levacetylmethadol (INN), levomethadyl acetate (USAN), OrLAAM (trade name) or levo-α-acetylmethadol (LAAM) is a synthetic opioid similar in structure to methadone. It has a long duration of action due to its active metabolites.
==Medical uses== LAAM is indicated as a second-line treatment for the treatment and management of opioid dependence if patients fail to respond to drugs like methadone or buprenorphine.
Excerpted from Wikipedia’s “levomethadyl acetate” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0