TROPANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H15N
Molecular Weight	125.2114
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2CC[C@@H]1CCC2

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	125.2114
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Iometopane: (123)I beta-CIT, dopascan injection, GPI 200, RTI 55.	2003	12952503
Tropane alkaloids from the bark of Erythroxylum vacciniifolium.	2003 Apr	12713400
Alkaloids from Brugmansia arborea (L.) Lagerhein reduce morphine withdrawal in vitro.	2003 Aug	12916089
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	14661759
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	12945769
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	12723962
Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.	2003 Nov 14	14604356
Synthesis and biological activity of 2-carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes.	2003 Nov 17	14592523
Synthesis and evaluation of iodine-123 labelled tricyclic tropanes as radioligands for the serotonin transporter.	2003 Oct	14499332
Molecular mechanism of citalopram and cocaine interactions with neurotransmitter transporters.	2003 Oct	12944499
Synthesis and pharmacological evaluation of (Z)-9-(heteroarylmethylene)-7-azatricyclo[4.3.1.0(3,7)]decanes: thiophene analogues as potent norepinephrine transporter inhibitors.	2003 Oct 20	14505672
Dopamine transporter as target for drug development of cocaine dependence medications.	2003 Oct 31	14612141
Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective.	2003 Sep	12946402
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.	2003 Sep	12885861
Pervilleine F, a new tropane alkaloid aromatic ester that reverses multidrug resistance.	2003 Sep-Oct	14666656
Tropane alkaloids from Latua pubiflora.	2003 Sep-Oct	14577619
Fragmentation pathway of dopamine transporter ligands: N-substituted-2beta-carbomethoxy-3beta-phenylnortropane derivatives.	2004 Apr 1	15030894
A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis.	2004 Apr 29	15101769
Nicotine's defensive function in nature.	2004 Aug	15314646
Tropane alkaloid production and shoot regeneration in hairy and adventitious root cultures of Duboisia myoporoides-D. leichhardtii hybrid.	2004 Aug	15305033
Synthesis of 8-thiabicyclo[3.2.1]oct-2-enes and their binding affinity for the dopamine and serotonin transporters.	2004 Dec 20	15546718
Haloperidol: towards further understanding of the structural contributions of its pharmacophoric elements at D2-like receptors.	2004 Dec 6	15501032
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	14767132
Synthesis and nicotinic receptor activity of a hydroxylated tropane.	2004 Jan 5	14684341
Covalent and noncovalent chemical modifications of arginine residues decrease dopamine transporter activity.	2004 Jun 15	15103693
Structure-activity relationships at monoamine transporters for a series of N-substituted 3alpha-(bis[4-fluorophenyl]methoxy)tropanes: comparative molecular field analysis, synthesis, and pharmacological evaluation.	2004 Jun 17	15189035
Comparison of tropane alkaloid spectra between Datura innoxia grown in Egypt and Bulgaria.	2004 Mar-Apr	15241922
Altered nitrogen metabolism associated with de-differentiated suspension cultures derived from root cultures of Datura stramonium studied by heteronuclear multiple bond coherence (HMBC) NMR spectroscopy.	2004 May	15073218
N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids.	2004 Nov	15568773
Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae).	2004 Nov-Dec	15666547
Winter cherry bugs feed on plant tropane alkaloids and de-epoxidize scopolamine to atropine.	2004 Oct	15609839
Morphological, chemical and functional analysis of catuaba preparations.	2004 Oct	15490329
Association of diamine oxidase and S-adenosylhomocysteine hydrolase in Nicotiana tabacum extracts.	2004 Sep	15604745
Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids.	2004 Sep	15221279
Total synthesis of (+)-cocaine via desymmetrization of a meso-dialdehyde.	2004 Sep 16	15355038
Synthesis, structural identification, and ligand binding of tropane ring analogs of paroxetine and an unexpected aza-bicyclo[3.2.2]nonane rearrangement product.	2005 Apr 1	15755646
Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist.	2005 Apr 22	15781147
Spatial orientation of the antagonist granisetron in the ligand-binding site of the 5-HT3 receptor.	2005 Aug	15914697
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	15879005
Striatal dopamine transporter imaging correlates with anxiety and depression symptoms in Parkinson's disease.	2005 Feb	15695780
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.	2005 Feb	15642710
Synthesis and biodistribution of [18F]FE@CIT, a new potential tracer for the dopamine transporter.	2005 Feb	15529336
Uniformly sized molecularly imprinted polymer for atropine and its application to the determination of atropine and scopolamine in pharmaceutical preparations containing Scopolia extract.	2005 Feb 23	15708662
[Voltage-activated potassium channel blockers inhibit anisodamine-induced relaxation of rabbit aortic smooth muscles precontracted with noradrenaline].	2005 Feb 25	15719131
Effects of long-term biogenic amine transporter blockade on receptor/G-protein coupling in rat brain.	2005 Jan	15617728
First-principle studies of intermolecular and intramolecular catalysis of protonated cocaine.	2005 Jul 30	15880781
Chemotaxonomy of the pantropical genus Merremia (Convolvulaceae) based on the distribution of tropane alkaloids.	2005 Jun	15922373
Calystegines in wild and cultivated Erythroxylum species.	2005 Jun	15907958
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	15753253
Time-dependent changes in receptor/G-protein coupling in rat brain following chronic monoamine transporter blockade.	2005 May	15644432

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:37:36 GMT 2023` Edited by `admin` on `Sat Dec 16 08:37:36 GMT 2023`
Record UNII	62QFG0728A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TROPANE

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