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
Modulation of the multidrug-resistance phenotype by new tropane alkaloid aromatic esters from Erythroxylum pervillei.	2001 Dec	11754602
Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: potential positron emission tomography (PET) imaging agents for the dopamine transporter.	2001 Dec 3	11714608
Tropane alkaloids in adventitious root cultures of Physochlaina physaloides.	2002	12638186
Medicinal herb Erycibe henri Prain ("Ting Kung Teng") resulting in acute cholinergic syndrome.	2002	12126192
Nitrogen inversion in cyclic amines and the bicyclic effect.	2002 Dec 27	12492327
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).	2002 Feb 1	11855731
PET imaging of dopamine transporters in the human brain using [(11)C]-beta-CPPIT, a cocaine derivative lacking the 2 beta-ester function.	2002 Jan	11786272
The Interactions of the 5-HT(3) receptor with arylpiperazine, tropane, and quinuclidine ligands.	2002 Jun	12052196
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	11814868
Synthesis and biological evaluation of 2-substituted 3beta-tolyltropane derivatives at dopamine, serotonin, and norepinephrine transporters.	2002 Mar 14	11881989
Characterization of tropane alkaloid aromatic esters that reverse the multidrug-resistance phenotype.	2002 May-Jun	12168815
Analysis of tropane and related alkaloids.	2002 Nov 29	12458942
Quantitative analysis of tropane alkaloids in biological materials by gas chromatography-mass spectrometry.	2002 Nov 5	12427448
Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process.	2002 Oct	12359518
Pervilleines B and C, new tropane alkaloid aromatic esters that reverse the multidrug-resistance in the hollow fiber assay.	2002 Oct 8	12104043
Alkaloids from Brugmansia arborea (L.) Lagerhein reduce morphine withdrawal in vitro.	2003 Aug	12916089
Effect of pmt gene overexpression on tropane alkaloid production in transformed root cultures of Datura metel and Hyoscyamus muticus.	2003 Jan	12493848
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
Molecular mechanism of citalopram and cocaine interactions with neurotransmitter transporters.	2003 Oct	12944499
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
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
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
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
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 `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