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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:43:42 UTC
HMDB IDHMDB0015502
Secondary Accession Numbers
  • HMDB15502
Metabolite Identification
Common NameMethadyl Acetate
DescriptionAlphacetylmethadol, also known as levomethadyl or LAAM, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Alphacetylmethadol is a drug which is used mainly in the treatment of narcotic dependence. Based on a literature review very few articles have been published on Alphacetylmethadol.
Structure
Data?1582753304
Synonyms
ValueSource
AcetylmethadolKegg
Methadyl acetic acidHMDB
BetamethadolHMDB
Levo-alpha-acetylmethadolHMDB
LevomethadylHMDB
Levomethadyl acetateHMDB
MethadolHMDB
6-(Dimethylamino)-4,4-diphenyl-3-heptanol acetateHMDB
DimepheptanolHMDB
LAAMHMDB
LevoacetylmethadolHMDB
Levomethadyl acetate hydrochlorideHMDB
ORLAAMHMDB
AcemethadoneHMDB
Levo alpha acetylmethadolHMDB
(3R,6R)-3-Acetoxy-6-dimethylamino-4,4-diphenylheptaneHMDB
AmidolacetateHMDB
AlphacetylmethadolMeSH, HMDB
Chemical FormulaC23H31NO2
Average Molecular Weight353.4977
Monoisotopic Molecular Weight353.235479241
IUPAC Name6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate
Traditional Namemethadyl acetate
CAS Registry Number509-74-0
SMILES
CCC(OC(C)=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
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
InChI KeyXBMIVRRWGCYBTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Aralkylamine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.27HANSCH,C ET AL. (1995)
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP10(4.78) g/LALOGPS
logP10(4.88) g/LChemAxon
logS10(-5.3) g/LALOGPS
pKa (Strongest Basic)9.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.86 m³·mol⁻¹ChemAxon
Polarizability40.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.95431661259
DarkChem[M-H]-184.631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methadyl Acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-9081000000-c21fec0e8e70744482b42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methadyl Acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methadyl Acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 10V, Positive-QTOFsplash10-0udi-0029000000-c28a76d17f554d7ba4392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 20V, Positive-QTOFsplash10-022c-7096000000-e5337d3be9cfb3f23f092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 40V, Positive-QTOFsplash10-0fkc-5190000000-113274c2b46b6767d5b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 10V, Negative-QTOFsplash10-0udi-1019000000-248c95ec24dae32993842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 20V, Negative-QTOFsplash10-0nmi-4039000000-abf719229500214241e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 40V, Negative-QTOFsplash10-05mo-9081000000-e357c686965cbd06e26c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 10V, Positive-QTOFsplash10-0udi-0089000000-c427737dde1e774f49722021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 20V, Positive-QTOFsplash10-0pb9-2193000000-2a568014680a63d6012f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 40V, Positive-QTOFsplash10-06di-3790000000-c1eca86692e210363e6a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 10V, Negative-QTOFsplash10-0zfr-6019000000-270678fc70b14132747a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methadyl Acetate 40V, Negative-QTOFsplash10-056r-2930000000-da1f57c344e66e9ff1122021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01433 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01433 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01433
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10080
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylmethadol
METLIN IDNot Available
PubChem Compound10517
PDB IDNot Available
ChEBI ID385936
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
References
  1. Mancino MJ, McGaugh J, Feldman Z, Poling J, Oliveto A: Effect of PTSD diagnosis and contingency management procedures on cocaine use in dually cocaine- and opioid-dependent individuals maintained on LAAM: a retrospective analysis. Am J Addict. 2010 Mar-Apr;19(2):169-77. doi: 10.1111/j.1521-0391.2009.00025.x. [PubMed:20163389 ]
  2. Walczak SA, Makman MH, Gardner EL: Acetylmethadol metabolites influence opiate receptors and adenylate cyclase in amygdala. Eur J Pharmacol. 1981 Jul 10;72(4):343-9. [PubMed:6268422 ]
  3. Wolstein J, Gastpar M, Finkbeiner T, Heinrich C, Heitkamp R, Poehlke T, Scherbaum N: A randomized, open-label trial comparing methadone and Levo-Alpha-Acetylmethadol (LAAM) in maintenance treatment of opioid addiction. Pharmacopsychiatry. 2009 Jan;42(1):1-8. doi: 10.1055/s-0028-1083818. Epub 2009 Jan 19. [PubMed:19153939 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]