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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:28 UTC
Update Date2021-09-14 15:45:57 UTC
HMDB IDHMDB0041812
Secondary Accession Numbers
  • HMDB41812
Metabolite Identification
Common Name6-Acetylmorphine
Description6-Acetylmorphine, also known as 6-MAM or morphine 6-acetate, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. 6-Acetylmorphine is a very strong basic compound (based on its pKa). Within humans, 6-acetylmorphine participates in a number of enzymatic reactions. In particular, 6-acetylmorphine and acetic acid can be biosynthesized from heroin; which is mediated by the enzymes liver carboxylesterase 1 and cocaine esterase. In addition, 6-acetylmorphine can be converted into morphine and acetic acid through its interaction with the enzymes liver carboxylesterase 1 and cocaine esterase. In humans, 6-acetylmorphine is involved in heroin metabolism pathway. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Structure
Data?1563863705
Synonyms
ValueSource
6-MAMHMDB
6-MonoacetylmorphineHMDB
6-O-AcetylmorphineHMDB
6-O-MonoacetylmorphineHMDB
a-Monoacetyl-morphineHMDB
MonoacetylmorphineHMDB
Morphine 6-acetateHMDB
O6 MonoacetylmorphineHMDB
6-MAM CPDHMDB
Morphine-6-acetateHMDB
6-(0-Acetyl)morphineHMDB
6-O-Monoacetylmorphine hydrochloride, (5alpha,6alpha)-isomerHMDB
Chemical FormulaC19H21NO4
Average Molecular Weight327.3743
Monoisotopic Molecular Weight327.147058165
IUPAC Name10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate
Traditional Name10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate
CAS Registry Number2784-73-8
SMILES
CN1CCC23C4OC5=C(O)C=CC(CC1C2C=CC4OC(C)=O)=C35
InChI Identifier
InChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3
InChI KeyJJGYGPZNTOPXGV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP1.9ALOGPS
logP1.31ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.27 m³·mol⁻¹ChemAxon
Polarizability34.71 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available176.45431661259
DarkChem[M-H]-PredictedNot Available172.24631661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
6-Acetylmorphine,1TMS,#12595.4187https://arxiv.org/abs/1905.12712
6-Acetylmorphine,1TBDMS,#12840.917https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8092000000-9d66631288fe4f66c7902017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-8009000000-52b47a4992bdbd81c4842017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-8092000000-9d66631288fe4f66c7902021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0129000000-5471df3df6acdae4d4b12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - -1V, Positivesplash10-004i-0129000000-5842d0f2507c059681e62021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1098000000-93911ba27c15dd97e3e22016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n0-1092000000-ddc7bfbf778152ac0e232016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aym-3090000000-cf6e08778a9a8ff75a322016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-3059000000-c3b4e5af4d0f8422135c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4093000000-4656131edcd16df763322016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-8090000000-a6a34ebc747c34b19fd02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2079000000-23e754d670ade7a54f3c2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9021000000-0950ccebf50cfaad3a1e2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adi-7079000000-4fb47d8b0e5e8226521a2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-521926133e29807da7942021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0029000000-2962ac8b01632069e30b2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-0093000000-d9e55425ae545b6b80f12021-09-07View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID453890
KEGG Compound IDC11781
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylmorphine
METLIN IDNot Available
PubChem Compound520352
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available