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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:44 UTC
HMDB IDHMDB0015502
Secondary Accession Numbers
  • HMDB15502
Metabolite Identification
Common NameMethadyl Acetate
DescriptionMethadyl Acetate, also known as acetylmethadol 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. Methadyl Acetate is a drug. Methadyl Acetate is a very strong basic compound (based on its pKa). In humans, methadyl acetate is involved in methadyl acetate action pathway. Acetylmethadol has an ACSCN of 9601. Hence, acetylmethadol has four possible optical isomers. All of these isomers have been shown to partially or fully substitute for the discriminative stimulus effects of heroin in rats, and thus it can be inferred that, in addition to LAAM which is used clinically as such, they are all likely to be active opioid analgesics in humans. It is a racemic mixture of alphacetylmethadol (α-acetylmethadol) and betacetylmethadol (β-acetylmethadol), which are in turn racemic mixtures of levacetylmethadol (LAAM; L-α-acetylmethadol) and D-α-acetylmethadol and L-β-acetylmethadol and D-β-acetylmethadol, respectively. The isomers have individual ACSCNs, which are as follows: Alphacetylmethadol 9603, Betacetylmethadol 9607, LAAM 9648. All of the above have annual manufacturing quotas of 2 grammes as of 2013, except LAAM, which is 4 grammes. In the United States, acetylmethadol and its individual isomers are all Schedule I drugs under the Controlled Substances Act, except LAAM, which is Schedule II and was used clinically until 2003.
Structure
Data?1582753304
Synonyms
ValueSource
AcetylmethadolKegg
Methadyl acetic acidGenerator
BetamethadolHMDB
AlphacetylmethadolHMDB
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
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:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.27HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP4.78ALOGPS
logP4.88ChemAxon
logS-5.3ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-9081000000-c21fec0e8e70744482b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-c28a76d17f554d7ba439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022c-7096000000-e5337d3be9cfb3f23f09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkc-5190000000-113274c2b46b6767d5b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1019000000-248c95ec24dae3299384Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nmi-4039000000-abf719229500214241e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9081000000-e357c686965cbd06e26cSpectrum
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
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 ]