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
Spatial orientation of the antagonist granisetron in the ligand-binding site of the 5-HT3 receptor.	2005-08	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.	2005-08	15879005
First-principle studies of intermolecular and intramolecular catalysis of protonated cocaine.	2005-07-30	15880781
Chemotaxonomy of the pantropical genus Merremia (Convolvulaceae) based on the distribution of tropane alkaloids.	2005-06	15922373
Calystegines in wild and cultivated Erythroxylum species.	2005-06	15907958
Time-dependent changes in receptor/G-protein coupling in rat brain following chronic monoamine transporter blockade.	2005-05	15644432
Molecular dissection of tropisetron, an alpha7 nicotinic acetylcholine receptor-selective partial agonist.	2005-04-22	15781147
Synthesis, structural identification, and ligand binding of tropane ring analogs of paroxetine and an unexpected aza-bicyclo[3.2.2]nonane rearrangement product.	2005-04-01	15755646
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.	2005-03	15753253
[Voltage-activated potassium channel blockers inhibit anisodamine-induced relaxation of rabbit aortic smooth muscles precontracted with noradrenaline].	2005-02-25	15719131
Uniformly sized molecularly imprinted polymer for atropine and its application to the determination of atropine and scopolamine in pharmaceutical preparations containing Scopolia extract.	2005-02-23	15708662
Striatal dopamine transporter imaging correlates with anxiety and depression symptoms in Parkinson's disease.	2005-02	15695780
Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.	2005-02	15642710
Synthesis and biodistribution of [18F]FE@CIT, a new potential tracer for the dopamine transporter.	2005-02	15529336
Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae).	2005-01-26	15666547
Effects of long-term biogenic amine transporter blockade on receptor/G-protein coupling in rat brain.	2005-01	15617728
Synthesis of 8-thiabicyclo[3.2.1]oct-2-enes and their binding affinity for the dopamine and serotonin transporters.	2004-12-20	15546718
Haloperidol: towards further understanding of the structural contributions of its pharmacophoric elements at D2-like receptors.	2004-12-06	15501032
N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids.	2004-11	15568773
Winter cherry bugs feed on plant tropane alkaloids and de-epoxidize scopolamine to atropine.	2004-10	15609839
Morphological, chemical and functional analysis of catuaba preparations.	2004-10	15490329
Total synthesis of (+)-cocaine via desymmetrization of a meso-dialdehyde.	2004-09-16	15355038
Association of diamine oxidase and S-adenosylhomocysteine hydrolase in Nicotiana tabacum extracts.	2004-09	15604745
Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids.	2004-09	15221279
Nicotine's defensive function in nature.	2004-08	15314646
Tropane alkaloid production and shoot regeneration in hairy and adventitious root cultures of Duboisia myoporoides-D. leichhardtii hybrid.	2004-08	15305033
Comparison of tropane alkaloid spectra between Datura innoxia grown in Egypt and Bulgaria.	2004-07-10	15241922
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.	2004-06-17	15189035
Covalent and noncovalent chemical modifications of arginine residues decrease dopamine transporter activity.	2004-06-15	15103693
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.	2004-05	15073218
A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis.	2004-04-29	15101769
Fragmentation pathway of dopamine transporter ligands: N-substituted-2beta-carbomethoxy-3beta-phenylnortropane derivatives.	2004-04-01	15030894
N-(2-Fluoroethyl)-3beta-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2alpha-carboxamide: a new cocaine derivative with equatorially attached ligands.	2004-02	14767132
Synthesis and nicotinic receptor activity of a hydroxylated tropane.	2004-01-05	14684341
Pervilleine F, a new tropane alkaloid aromatic ester that reverses multidrug resistance.	2003-12-12	14666656
On-line identification of tropane alkaloids from Erythroxylum vacciniifolium by liquid chromatography-UV detection-multiple mass spectrometry and liquid chromatography-nuclear magnetic resonance spectrometry.	2003-12-05	14661759
Synthesis and biological activity of 2-carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes.	2003-11-17	14592523
Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.	2003-11-14	14604356
Dopamine transporter as target for drug development of cocaine dependence medications.	2003-10-31	14612141
Tropane alkaloids from Latua pubiflora.	2003-10-28	14577619
Synthesis and pharmacological evaluation of (Z)-9-(heteroarylmethylene)-7-azatricyclo[4.3.1.0(3,7)]decanes: thiophene analogues as potent norepinephrine transporter inhibitors.	2003-10-20	14505672
Synthesis and evaluation of iodine-123 labelled tricyclic tropanes as radioligands for the serotonin transporter.	2003-10	14499332
Molecular mechanism of citalopram and cocaine interactions with neurotransmitter transporters.	2003-10	12944499
Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective.	2003-09	12946402
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.	2003-09	12885861
Alkaloids from Brugmansia arborea (L.) Lagerhein reduce morphine withdrawal in vitro.	2003-08	12916089
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.	2003-06-07	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.	2003-05-08	12723962
Tropane alkaloids from the bark of Erythroxylum vacciniifolium.	2003-04	12713400
Iometopane: (123)I beta-CIT, dopascan injection, GPI 200, RTI 55.	2003	12952503

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:12:57 GMT 2025` Edited by `admin` on `Mon Mar 31 22:12:57 GMT 2025`
Record UNII	62QFG0728A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TROPANE

Systematic Name

English

2,3-DIHYDRO-8-METHYLNORTROPIDINE

Preferred Name

English

N-METHYL-8-AZABICYCLO(3.2.1)OCTANE

Systematic 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