6-monoacetylmorphine

General

Type : Natural, Drug, Isoquinoline, Alkaloid

Chemical_Nomenclature : (9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl) acetate

Canonical SMILES : CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C

InChI : 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

InChIKey : JJGYGPZNTOPXGV-UHFFFAOYSA-N

Other name(s) : O6 Monoacetylmorphine  ||  Monoacetylmorphine  ||  Morphine 6-acetate  ||  6-O-Acetylmorphine  ||  6-MAM


MW : 327.38

Formula : C19H21NO4

CAS_number :

PubChem : 520352

UniChem : JJGYGPZNTOPXGV-UHFFFAOYSA-N

Target

Families : BCHE

References (8)

Title : Kinetic characterization of cholinesterases and a therapeutically valuable cocaine hydrolase for their catalytic activities against heroin and its metabolite 6-monoacetylmorphine - Kim_2018_Chem.Biol.Interact_293_107
Author(s) : Kim K , Yao J , Jin Z , Zheng F , Zhan CG
Ref : Chemico-Biological Interactions , 293 :107 , 2018
Abstract :
PubMedSearch : Kim_2018_Chem.Biol.Interact_293_107
PubMedID: 30080993

Title : Possible mechanism for inhibition of morphine formation from 6-acetylmorphine after intake of street heroin - Andersson_2015_Forensic.Sci.Int_252_150
Author(s) : Andersson M , Bjorkhem-Bergman L , Beck O
Ref : Forensic Science International , 252 :150 , 2015
Abstract :
PubMedSearch : Andersson_2015_Forensic.Sci.Int_252_150
PubMedID: 26002801

Title : Reaction pathways and free energy profiles for cholinesterase-catalyzed hydrolysis of 6-monoacetylmorphine - Qiao_2014_Org.Biomol.Chem_12_2214
Author(s) : Qiao Y , Han K , Zhan CG
Ref : Org Biomol Chem , 12 :2214 , 2014
Abstract :
PubMedSearch : Qiao_2014_Org.Biomol.Chem_12_2214
PubMedID: 24595354

Title : Diacetylmorphine degradation to 6-monoacetylmorphine and morphine in cell culture: implications for in vitro studies - Hutchinson_2002_Eur.J.Pharmacol_453_27
Author(s) : Hutchinson MR , Somogyi AA
Ref : European Journal of Pharmacology , 453 :27 , 2002
Abstract :
PubMedSearch : Hutchinson_2002_Eur.J.Pharmacol_453_27
PubMedID: 12393056

Title : Human erythrocyte but not brain acetylcholinesterase hydrolyses heroin to morphine - Salmon_1999_Clin.Exp.Pharmacol.Physiol_26_596
Author(s) : Salmon AY , Goren Z , Avissar Y , Soreq H
Ref : Clinical & Experimental Pharmacology & Physiology , 26 :596 , 1999
Abstract :
PubMedSearch : Salmon_1999_Clin.Exp.Pharmacol.Physiol_26_596
PubMedID: 10474772

Title : Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases - Kamendulis_1996_J.Pharmacol.Exp.Ther_279_713
Author(s) : Kamendulis LM , Brzezinski MR , Pindel EV , Bosron WF , Dean RA
Ref : Journal of Pharmacology & Experimental Therapeutics , 279 :713 , 1996
Abstract :
PubMedSearch : Kamendulis_1996_J.Pharmacol.Exp.Ther_279_713
PubMedID: 8930175

Title : Alteration of in vivo and in vitro effects of heroin by esterase inhibition - Gianutsos_1986_Toxicol.Appl.Pharmacol_82_14
Author(s) : Gianutsos G , Cohen SD , Carlson G , Heyman R , Salva P , Morrow G , Hite GJ
Ref : Toxicol Appl Pharmacol , 82 :14 , 1986
Abstract :
PubMedSearch : Gianutsos_1986_Toxicol.Appl.Pharmacol_82_14
PubMedID: 3003965

Title : Pharmacokinetics of morphine and its surrogates IV: Pharmacokinetics of heroin and its derived metabolites in dogs - Garrett_1980_J.Pharm.Sci_69_1116
Author(s) : Garrett ER , Gurkan T
Ref : J Pharm Sci , 69 :1116 , 1980
Abstract :
PubMedSearch : Garrett_1980_J.Pharm.Sci_69_1116
PubMedID: 7420276