6-ACETYLMORPHINE

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 Search

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

Title	Date	PubMed
Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases.	1996 Nov	8930175
Fast analysis of drugs in a single hair.	1998 Dec	9835076
Determination of opiates in serum, saliva and hair addicted persons.	2001	11450354
Physician recognition of active drug use in HIV-infected patients is lower than validity of patient's self-reported drug use.	2001 Feb	11302118
Misinterpretation of a urinary 6-monoacetyl morphine concentration.	2001 Jan	11210918
Laboratory analysis of remotely collected oral fluid specimens for opiates by immunoassay.	2001 Jul-Aug	11499883
Concentration ratios of morphine to codeine in blood of impaired drivers as evidence of heroin use and not medication with codeine.	2001 Nov	11673366
Serum naltrexone and 6-beta-naltrexol levels from naltrexone implants can block very large amounts of heroin: a report of two cases.	2002 Jul	12126492
Application of the CEDIA 6-MAM assay to routine drugs-of-abuse screening.	2002 May-Jun	12054365
Diacetylmorphine degradation to 6-monoacetylmorphine and morphine in cell culture: implications for in vitro studies.	2002 Oct 18	12393056
Optimized conditions for simultaneous determination of opiates, cocaine and benzoylecgonine in hair samples by GC--MS.	2003 Dec 17	14642715
Determination of drugs of abuse in hair: evaluation of external heroin contamination and risk of false positives.	2003 Jan 28	12590046
Determination of opiates in biological samples through the analysis of heptafluorobutyric derivatives by gas chromatography/negative ion chemical ionization mass spectrometry.	2003 Sep	14505329
Component analysis of illicit heroin samples with GC/MS and its application in source identification.	2004 Jan	14979348
Comparison of the Microgenics CEDIA heroin metabolite (6-AM) and the Roche Abuscreen ONLINE opiate immunoassays for the detection of heroin use in forensic urine samples.	2004 Sep	15516301
Evaluation of the Cedia heroin metabolite (6-AM) immunoassay with urine specimens from A criminal justice drug-testing program.	2005 Apr	15842764
Surface-activated chemical ionization ion trap mass spectrometry in the analysis of drugs in dilute urine samples. Part II: analysis of morphine and other street drugs.	2005 Dec	16320295
Morphine and 6-monoacetylmorphine in hair of heroin users: use of invalid extraction procedures generates erroneous conclusions.	2005 Jan-Feb	15808019
Mechanisms of mu opioid receptor/G-protein desensitization in brain by chronic heroin administration.	2005 Jul 22	15890372
GC-MS quantitation of codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone in blood.	2005 Jul-Aug	16105253
Direct injection determination of benzoylecgonine, heroin, 6-monoacetylmorphine and morphine in serum by MLC.	2005 May 6	15909530
Feasibility and acceptability of an intranasal diamorphine spray as an alternative to injectable diamorphine for maintenance treatment.	2006	16543744
HPLC-DAD determination of opioids, cocaine and their metabolites in plasma.	2006 Aug 10	16300917
Acetylcodeine as a marker of illicit heroin abuse in oral fluid samples.	2006 Jul-Aug	16872567
Comparison of the various opiate alkaloid contaminants and their metabolites found in illicit heroin with 6-monoacetyl morphine as indicators of heroin ingestion.	2006 May	16803666
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 Feb	17304145
Simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, oxycodone, and 6-acetylmorphine in urine, serum, plasma, whole blood, and meconium by LC-MS-MS.	2007 Jan-Feb	17389078
Stability studies of principal illicit drugs in oral fluid: preparation of reference materials for external quality assessment schemes.	2007 Oct	17898661
Determination of morphine and 6-acetylmorphine in blood with use of dried blood spots.	2008 Dec	18978519
Error in the article: "driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood".	2008 Jun	18544226
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 Sep	18713513
Simultaneous determination of morphine, codeine, 6-acetylmorphine, cocaine and benzoylecgonine in hair by liquid chromatography/electrospray ionization tandem mass spectrometry.	2009 Apr	19241414
Criteria for opiate identification using liquid chromatography linked to tandem mass spectrometry: problems in routine practice.	2009 Jan	19103958
Multiclass analysis of illicit drugs in plasma and oral fluids by LC-MS/MS.	2009 Jan	18982317
Distribution of 6-monoacetylmorphine and morphine in head and pubic hair from heroin-related deaths.	2009 Jan 10	19062205
Optimization of a rapid microwave-assisted extraction method for the simultaneous determination of opiates, cocaine and their metabolites in human hair.	2009 Jun 15	19467936
Response to postcard from Sweden.	2009 Nov	19782329
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 Oct	19874645
On-line stacking and sweeping capillary electrophoresis for detecting heroin metabolites in human urine.	2009 Oct 30	19439308
[Impact of slow-release oral morphine on drug abusing habits in Austria].	2010	20605006
Quantitation of opioids in blood and urine using gas chromatography-mass spectrometry (GC-MS).	2010	20077092
Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin.	2010 Apr	20406541
Forensic toxicology findings in deaths involving gamma-hydroxybutyrate.	2010 Jan	19048269
Microwave-assisted high-throughput derivatization techniques utilizing silicon carbide microtiter platforms.	2010 Jan 1	19962705
Biomarkers of opiate use.	2010 Nov	20946276

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

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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