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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:14:03 UTC
Update Date2019-07-23 07:15:38 UTC
HMDB IDHMDB0061036
Secondary Accession Numbers
  • HMDB61036
Metabolite Identification
Common Namenoracymethadol
Descriptionnoracymethadol, also known as NLAAM, 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. noracymethadol is a very strong basic compound (based on its pKa). and is also controlled internationally under the United Nations Single Convention on Narcotic Drugs of 1961. Noracymethadol is an acetyl ester of methadol and it can be said with some precision that it is either the heroin or 6-monoacetylmorphine analogue of methadol, and being a methadol it exhibits optical isomerism. Similarly to many of its analogues, noracymethadol is a Schedule I controlled substance in the United States with an ACSCN of 9633 and 2013 annual manufacturing quota of 12 grammes. The other methadols (acetylmethadol, methadol &c) have at least four optical isomers (see Orlaam). Other side effects included salivation, ataxia, and respiratory depression that was reversible by naloxone. The salts known are the gluconate (free base conversion ratio 0.633) and hydrochloride (0.903). In a clinical trial of postpartum patients it was reported to produce analgesia comparable to that of morphine but with less nausea, dizziness, and drowsiness. Noracymethadol (INN) is a synthetic opioid analgesic related to methadone that was never marketed.
Structure
Data?1563866138
Synonyms
ValueSource
1 alpha-AcetylnormethadolHMDB
N-Desmethyl-1-alpha-acetylmethadolHMDB
NLAAMHMDB
L-alpha-NoracetylmethadolHMDB
Paracymethadol hydrochlorideHMDB
6-(Methylamino)-4,4-diphenyl-3-heptanol acetateHMDB
Nor-laamHMDB
NoracetylmethadolHMDB
ParacymethadolHMDB
Paracymethadol hydrochloride, (S-(r*,r*))-isomerHMDB
Paracymethadol, (R-(r*,r*))-isomerHMDB
Paracymethadol, (S-(r*,r*))-(-)-isomerHMDB
Paracymethadol hydrochloride, (r*,r*)-(+-)-isomerHMDB
Paracymethadol, (r*,r*)-(+-)-isomerHMDB
Nor-levomethadyl acetic acidGenerator
Chemical FormulaC22H29NO2
Average Molecular Weight339.4712
Monoisotopic Molecular Weight339.219829177
IUPAC Name6-(methylamino)-4,4-diphenylheptan-3-yl acetate
Traditional Name6-(methylamino)-4,4-diphenylheptan-3-yl acetate
CAS Registry NumberNot Available
SMILES
CCC(OC(C)=O)C(CC(C)NC)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C22H29NO2/c1-5-21(25-18(3)24)22(16-17(2)23-4,19-12-8-6-9-13-19)20-14-10-7-11-15-20/h6-15,17,21,23H,5,16H2,1-4H3
InChI KeyVWCUGCYZZGRKEE-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
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen 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

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00071 g/LALOGPS
logP4.85ALOGPS
logP4.5ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity112.56 m³·mol⁻¹ChemAxon
Polarizability38.83 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, Positivesplash10-000i-8091000000-2a8d63f130c37f8b8aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0059000000-b09c48f2e226d7ac372eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0535-2092000000-66fd2bc69fec018fa64dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apr-5090000000-6b7d44d0466b053eec0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1059000000-1235a19d2b1ca2c884b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052k-5095000000-6073042107914cc65a6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9070000000-b0834e7bdf3b8dc00c43Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNoracymethadol
      METLIN IDNot Available
      PubChem Compound15129
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available