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

Details

Stereochemistry ACHIRAL
Molecular Formula C8H15N
Molecular Weight 125.2117
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROPANE

SMILES

CN1[C@@]2([H])CCC[C@]1([H])CC2

InChI

InChIKey=XLRPYZSEQKXZAA-OCAPTIKFSA-N
InChI=1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+

HIDE SMILES / InChI

Molecular Formula C8H15N
Molecular Weight 125.2117
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides.
2002
Tropane alkaloids in adventitious root cultures of Physochlaina physaloides.
2002
Medicinal herb Erycibe henri Prain ("Ting Kung Teng") resulting in acute cholinergic syndrome.
2002
Reversal of multidrug resistance by tropane alkaloids from the stems of Erythroxylum rotundifolium.
2002 Apr
Further studies on conformationally constrained tricyclic tropane analogues and their uptake inhibition at monoamine transporter sites: synthesis of (Z)-9-(substituted arylmethylene)-7-azatricyclo[4.3.1.0(3,7)]decanes as a novel class of serotonin transporter inhibitors.
2002 Apr 25
Six clinical cases of Mandragora autumnalis poisoning: diagnosis and treatment.
2002 Dec
New tropane alkaloids from Erythroxylum moonii.
2002 Jun
The Interactions of the 5-HT(3) receptor with arylpiperazine, tropane, and quinuclidine ligands.
2002 Jun
Novel potent 5-HT(3) receptor ligands based on the pyrrolidone structure: synthesis, biological evaluation, and computational rationalization of the ligand-receptor interaction modalities.
2002 Mar
Characterization of tropane alkaloid aromatic esters that reverse the multidrug-resistance phenotype.
2002 May-Jun
One-pot synthesis of tropinone by tandem (domino) ene-type reactions of acetone silyl enol ethers.
2002 Nov 21
Analysis of tropane and related alkaloids.
2002 Nov 29
Quantitative analysis of tropane alkaloids in biological materials by gas chromatography-mass spectrometry.
2002 Nov 5
Pervilleines B and C, new tropane alkaloid aromatic esters that reverse the multidrug-resistance in the hollow fiber assay.
2002 Oct 8
Tropane alkaloids from the bark of Erythroxylum vacciniifolium.
2003 Apr
Alkaloids from Brugmansia arborea (L.) Lagerhein reduce morphine withdrawal in vitro.
2003 Aug
On-line identification of tropane alkaloids from Erythroxylum vacciniifolium by liquid chromatography-UV detection-multiple mass spectrometry and liquid chromatography-nuclear magnetic resonance spectrometry.
2003 Dec 5
Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus.
2003 Jan
Effect of HD-23, a potent long acting cocaine-analog, on cocaine self-administration in rats.
2003 Jun
Highly diastereoselective 1,3-dipolar cycloaddition reactions of trans-2-methylene-1,3-dithiolane 1,3-dioxide with 3-oxidopyridinium and 3-oxidopyrylium betaines: a route to the tropane skeleton.
2003 Jun 7
Biaryl analogues of conformationally constrained tricyclic tropanes as potent and selective norepinephrine reuptake inhibitors: synthesis and evaluation of their uptake inhibition at monoamine transporter sites.
2003 May 8
Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.
2003 Nov 14
Synthesis and evaluation of iodine-123 labelled tricyclic tropanes as radioligands for the serotonin transporter.
2003 Oct
Molecular mechanism of citalopram and cocaine interactions with neurotransmitter transporters.
2003 Oct
Dopamine transporter as target for drug development of cocaine dependence medications.
2003 Oct 31
Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective.
2003 Sep
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.
2003 Sep
Pervilleine F, a new tropane alkaloid aromatic ester that reverses multidrug resistance.
2003 Sep-Oct
Tropane alkaloids from Latua pubiflora.
2003 Sep-Oct
Fragmentation pathway of dopamine transporter ligands: N-substituted-2beta-carbomethoxy-3beta-phenylnortropane derivatives.
2004 Apr 1
Haloperidol: towards further understanding of the structural contributions of its pharmacophoric elements at D2-like receptors.
2004 Dec 6
N-(2-Fluoroethyl)-3beta-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2alpha-carboxamide: a new cocaine derivative with equatorially attached ligands.
2004 Feb
Synthesis and nicotinic receptor activity of a hydroxylated tropane.
2004 Jan 5
Comparison of tropane alkaloid spectra between Datura innoxia grown in Egypt and Bulgaria.
2004 Mar-Apr
N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids.
2004 Nov
Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae).
2004 Nov-Dec
Winter cherry bugs feed on plant tropane alkaloids and de-epoxidize scopolamine to atropine.
2004 Oct
Morphological, chemical and functional analysis of catuaba preparations.
2004 Oct
Total synthesis of (+)-cocaine via desymmetrization of a meso-dialdehyde.
2004 Sep 16
Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist.
2005 Apr 22
Spatial orientation of the antagonist granisetron in the ligand-binding site of the 5-HT3 receptor.
2005 Aug
Recognition of benztropine by the dopamine transporter (DAT) differs from that of the classical dopamine uptake inhibitors cocaine, methylphenidate, and mazindol as a function of a DAT transmembrane 1 aspartic acid residue.
2005 Aug
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.
2005 Feb
Synthesis and biodistribution of [18F]FE@CIT, a new potential tracer for the dopamine transporter.
2005 Feb
[Voltage-activated potassium channel blockers inhibit anisodamine-induced relaxation of rabbit aortic smooth muscles precontracted with noradrenaline].
2005 Feb 25
Effects of long-term biogenic amine transporter blockade on receptor/G-protein coupling in rat brain.
2005 Jan
Chemotaxonomy of the pantropical genus Merremia (Convolvulaceae) based on the distribution of tropane alkaloids.
2005 Jun
Calystegines in wild and cultivated Erythroxylum species.
2005 Jun
Specific inhibitory action of anisodamine against a staphylococcal superantigenic toxin, toxic shock syndrome toxin 1 (TSST-1), leading to down-regulation of cytokine production and blocking of TSST-1 toxicity in mice.
2005 Mar
Time-dependent changes in receptor/G-protein coupling in rat brain following chronic monoamine transporter blockade.
2005 May
Patents
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:20:16 UTC 2021
Edited
by admin
on Fri Jun 25 22:20:16 UTC 2021
Record UNII
62QFG0728A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROPANE
MI  
Systematic Name English
N-METHYL-8-AZABICYCLO(3.2.1)OCTANE
Systematic Name English
2,3-DIHYDRO-8-METHYLNORTROPIDINE
Common Name English
TROPANE [MI]
Common Name English
8-METHYL-8-AZABICYCLO(3.2.1)OCTANE
Systematic Name English
8-AZABICYCLO(3.2.1)OCTANE, 8-METHYL-
Systematic Name English
1.ALPHA.H,5.ALPHA.H-TROPANE
Systematic Name English
Code System Code Type Description
PUBCHEM
637986
Created by admin on Fri Jun 25 22:20:17 UTC 2021 , Edited by admin on Fri Jun 25 22:20:17 UTC 2021
PRIMARY
CAS
529-17-9
Created by admin on Fri Jun 25 22:20:16 UTC 2021 , Edited by admin on Fri Jun 25 22:20:16 UTC 2021
PRIMARY
FDA UNII
62QFG0728A
Created by admin on Fri Jun 25 22:20:16 UTC 2021 , Edited by admin on Fri Jun 25 22:20:16 UTC 2021
PRIMARY
MERCK INDEX
M11226
Created by admin on Fri Jun 25 22:20:16 UTC 2021 , Edited by admin on Fri Jun 25 22:20:16 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
Tropane
Created by admin on Fri Jun 25 22:20:17 UTC 2021 , Edited by admin on Fri Jun 25 22:20:17 UTC 2021
PRIMARY
Related Record Type Details
DERIVATIVE -> PARENT