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Details

Stereochemistry RACEMIC
Molecular Formula C16H21N
Molecular Weight 227.3446
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MORPHINAN, (±)-

SMILES

[H][C@@]12CC3=CC=CC=C3[C@]4(CCCC[C@@]14[H])CCN2

InChI

InChIKey=INAXVFBXDYWQFN-XHSDSOJGSA-N
InChI=1S/C16H21N/c1-2-6-13-12(5-1)11-15-14-7-3-4-8-16(13,14)9-10-17-15/h1-2,5-6,14-15,17H,3-4,7-11H2/t14-,15+,16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H21N
Molecular Weight 227.3446
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Alkaloid biosynthesis in Papaver sp. cells in culture and during organogenesis.
2001 May-Jun
Morphinan derivatives--A review of the recent patent literature.
2003 Feb
New morphinan derivatives with negligible psychotropic effects attenuate convulsions induced by maximal electroshock in mice.
2003 Mar 7
Electrospray tandem mass spectrometric investigations of morphinans.
2003 Nov
1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway.
2004 Apr
Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots.
2004 Dec
Na+ modulation, inverse agonism, and anorectic potency of 4-phenylpiperidine opioid antagonists.
2004 Jun 28
Identification of opioid ligands possessing mixed micro agonist/delta antagonist activity among pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone [correction of hydropmorphone].
2004 Mar 11
6-oxo-morphinane oximes: pharmacology, chemistry and analytical application.
2004 Oct
Possible pharmacotherapy of the opioid kappa receptor agonist for drug dependence.
2004 Oct
Characterization of the complex morphinan derivative BU72 as a high efficacy, long-lasting mu-opioid receptor agonist.
2004 Sep 19
Protective effect of dextromethorphan against endotoxic shock in mice.
2005 Jan 15
A role for intra- and intercellular translocation in natural product biosynthesis.
2005 Jun
Opium Poppy (Papaver somniferum).
2006
Total synthesis of (+/-)-morphine.
2006 Nov 9
QSAR study on the antinociceptive activity of some morphinans.
2007 Jul
In-vitro investigation of oxazol and urea analogues of morphinan at opioid receptors.
2007 Jun 15
Levorphanol: the forgotten opioid.
2007 Mar
High-affinity carbamate analogues of morphinan at opioid receptors.
2007 Mar 15
Neuroprotective effects of cannabidiol in endotoxin-induced uveitis: critical role of p38 MAPK activation.
2008
Morphinane alkaloid dimers from Sinomenium acutum.
2008 Jan
Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM).
2008 Jul
Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.
2008 Jun 1
Neuronal apoptosis and inflammatory responses in the central nervous system of a rabbit treated with Shiga toxin-2.
2008 Mar 21
Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae.
2008 Sep
Recent developments in the chemistry of thebaine and its transformation products as pharmacological targets.
2009
Bisbenzylisoquinoline alkaloids from Cocculus pendulus.
2009
Univalent and bivalent ligands of butorphan: characteristics of the linking chain determine the affinity and potency of such opioid ligands.
2009 Dec 10
7α-Methoxy-carbonyl-6,7,8,14-tetra-hydro-6,14-endo-ethenothebaine.
2009 Mar 25
Biochemistry and occurrence of o-demethylation in plant metabolism.
2010
Biological indications of a novel "short" µ opiate receptor in domestic chicken.
2010 Aug 30
Interactive effects of endogenous morphine, nitric oxide, and ethanol on mitochondrial processes.
2010 Oct
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:12:19 GMT 2023
Edited
by admin
on Sat Dec 16 01:12:19 GMT 2023
Record UNII
OJ66WL736G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MORPHINAN, (±)-
Systematic Name English
(4ASR,10SR,10ASR)-1,3,4,9,10,10A-HEXAHYDRO-2H-10,4A-(IMINOETHANO)PHENANTHRENE
Systematic Name English
Code System Code Type Description
CAS
1215192-09-8
Created by admin on Sat Dec 16 01:12:19 GMT 2023 , Edited by admin on Sat Dec 16 01:12:19 GMT 2023
PRIMARY
FDA UNII
OJ66WL736G
Created by admin on Sat Dec 16 01:12:19 GMT 2023 , Edited by admin on Sat Dec 16 01:12:19 GMT 2023
PRIMARY
PUBCHEM
6857497
Created by admin on Sat Dec 16 01:12:19 GMT 2023 , Edited by admin on Sat Dec 16 01:12:19 GMT 2023
PRIMARY
WIKIPEDIA
Morphinan
Created by admin on Sat Dec 16 01:12:19 GMT 2023 , Edited by admin on Sat Dec 16 01:12:19 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE