U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO4
Molecular Weight 327.3743
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6-ACETYLMORPHINE

SMILES

CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@@H]2C=C[C@@H]4OC(C)=O)=C35

InChI

InChIKey=JJGYGPZNTOPXGV-SSTWWWIQSA-N
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/t12-,13+,15-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H21NO4
Molecular Weight 327.3743
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Simultaneous quantification of opiates and effect of pigmentation on its deposition in hair.
2010-11
Biomarkers of opiate use.
2010-11
Automated solid-phase extraction-liquid chromatography-tandem mass spectrometry analysis of 6-acetylmorphine in human urine specimens: application for a high-throughput urine analysis laboratory.
2010-10
[Simultaneous determination of opioid compounds in human urine by UPLC-MS/MS].
2010-06
Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin.
2010-04
Simultaneous quantitation of morphine, 6-acetylmorphine, codeine, 6-acetylcodeine and tramadol in hair using mixed-mode solid-phase extraction and gas chromatography-mass spectrometry.
2010-04
Heroin markers in hair of a narcotic police officer: active or passive exposure?
2010-03-20
Solid-phase microextraction for the detection of codeine, morphine and 6-monoacetylmorphine in human hair by gas chromatography-mass spectrometry.
2010-03-20
Microwave-assisted high-throughput derivatization techniques utilizing silicon carbide microtiter platforms.
2010-01-01
Forensic toxicology findings in deaths involving gamma-hydroxybutyrate.
2010-01
[Impact of slow-release oral morphine on drug abusing habits in Austria].
2010
Quantitation of morphine, codeine, hydrocodone, hydromorphone, oxycodone, oxymorphone, and 6-monoacetylmorphine (6-MAM) in urine, blood, serum, or plasma using liquid chromatography with tandem mass spectrometry detection.
2010
Quantitation of opioids in blood and urine using gas chromatography-mass spectrometry (GC-MS).
2010
Characteristics and comparative severity of respiratory response to toxic doses of fentanyl, methadone, morphine, and buprenorphine in rats.
2009-12-15
6-Acetylmorphine detected in the absence of morphine in pain management patients.
2009-12
Response to postcard from Sweden.
2009-11
Post-mortem toxicology is not quackery when done by qualified practitioners.
2009-11
On-line stacking and sweeping capillary electrophoresis for detecting heroin metabolites in human urine.
2009-10-30
A comparison of the validity of gas chromatography- mass spectrometry and liquid chromatography- tandem mass spectrometry analysis of urine samples for morphine, codeine, 6-acetylmorphine, and benzoylecgonine.
2009-10
Disposable microfluidic device with ultraviolet detection for highly resolved screening of illicit drugs.
2009-09
Optimization of a rapid microwave-assisted extraction method for the simultaneous determination of opiates, cocaine and their metabolites in human hair.
2009-06-15
Simultaneous determination of morphine, codeine, 6-acetylmorphine, cocaine and benzoylecgonine in hair by liquid chromatography/electrospray ionization tandem mass spectrometry.
2009-04
Distribution of 6-monoacetylmorphine and morphine in head and pubic hair from heroin-related deaths.
2009-01-10
Criteria for opiate identification using liquid chromatography linked to tandem mass spectrometry: problems in routine practice.
2009-01
Multiclass analysis of illicit drugs in plasma and oral fluids by LC-MS/MS.
2009-01
Determination of morphine and 6-acetylmorphine in blood with use of dried blood spots.
2008-12
Simultaneous detection and quantification of amphetamines, diazepam and its metabolites, cocaine and its metabolites, and opiates in hair by LC-ESI-MS-MS using a single extraction method.
2008-09
Group-selective antibodies based fluorescence immunoassay for monitoring opiate drugs.
2008-09
Development and validation of a solid-phase extraction gas chromatography-mass spectrometry method for the simultaneous quantification of methadone, heroin, cocaine and metabolites in sweat.
2008-09
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008-06
Error in the article: "driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood".
2008-06
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.
2008-05
Long-term stability of various drugs and metabolites in urine, and preventive measures against their decomposition with special attention to filtration sterilization.
2008-01-30
Stability studies of principal illicit drugs in oral fluid: preparation of reference materials for external quality assessment schemes.
2007-10
Simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, oxycodone, and 6-acetylmorphine in urine, serum, plasma, whole blood, and meconium by LC-MS-MS.
2007-03-29
Morphine and 6-acetylmorphine concentrations in blood, brain, spinal cord, bone marrow and bone after lethal acute or chronic diacetylmorphine administration to mice.
2007-03-02
Electrospray LC-MS method with solid-phase extraction for accurate determination of morphine-, codeine-, and ethylmorphine-glucuronides and 6-acetylmorphine in urine.
2007-03
Four years' experience in external proficiency testing programs for hair testing of drugs of abuse in Italy (HAIRVEQ) and comparison with the Society of Hair Testing program in 2005.
2007-02
Acetylcodeine as a marker of illicit heroin abuse in oral fluid samples.
2006-07-29
Comparison of the various opiate alkaloid contaminants and their metabolites found in illicit heroin with 6-monoacetyl morphine as indicators of heroin ingestion.
2006-05
[Preparation and characterization of anti-morphine vaccine antibody].
2006-05
Paradoxical results in urine drug testing for 6-acetylmorphine and total opiates: implications for best analytical strategy.
2006-03
Pharmacokinetics and pharmacokinetic variability of heroin and its metabolites: review of the literature.
2006-01
Fatal heroin intoxication in body packers in northern Thailand during the last decade: two case reports.
2006-01
Population pharmacokinetics of heroin and its major metabolites.
2006
Use of gas chromatography/mass spectrometry with positive chemical ionization for the determination of opiates in human oral fluid.
2006
Fast analysis of drugs in a single hair.
1998-12
Human liver carboxylesterase hCE-1: binding specificity for cocaine, heroin, and their metabolites and analogs.
1997-09
Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin.
1997-06-06
Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases.
1996-11
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:29:53 GMT 2025
Edited
by admin
on Mon Mar 31 18:29:53 GMT 2025
Record UNII
M5E47P1ZCH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
6-MAM
Preferred Name English
6-ACETYLMORPHINE
Common Name English
MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL- (5.ALPHA.,6.ALPHA.)-, 6-ACETATE
Systematic Name English
MAM
Common Name English
6-MONOACETYLMORPHINE
Common Name English
6-O-ACETYLMORPHINE
Common Name English
6-O-MONOACETYLMORPHINE
Common Name English
MONOACETYLMORPHINE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID60182154
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
CAS
2784-73-8
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
SMS_ID
100000125987
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
FDA UNII
M5E47P1ZCH
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
WIKIPEDIA
6-MONOACETYLMORPHINE
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
EVMPD
SUB32914
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
MESH
C026979
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
PUBCHEM
5462507
Created by admin on Mon Mar 31 18:29:53 GMT 2025 , Edited by admin on Mon Mar 31 18:29:53 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
6-MAM is a metabolite unique to heroin
Related Record Type Details
ACTIVE MOIETY