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

Details

Stereochemistry ACHIRAL
Molecular Formula C3H6
Molecular Weight 42.0797
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Cyclopropane

SMILES

C1CC1

InChI

InChIKey=LVZWSLJZHVFIQJ-UHFFFAOYSA-N
InChI=1S/C3H6/c1-2-3-1/h1-3H2

HIDE SMILES / InChI

Molecular Formula C3H6
Molecular Weight 42.0797
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Cyclopropane is a cycloalkane, consisting of three carbon atoms, linked to each other to form a ring. Cyclopropane was used as an anesthetic gas since the 1920s, due to being non-irritant, giving rapid induction, excellent relaxation, quiet respiration, and speedy recovery. However, the prolonged administration of cyclopropane may induce a reaction known as "cyclopropane shock", which manifests in a sudden decrease in blood pressure, potentially leading to cardiac dysrhythmia. Because of the toxicity and extreme flammability, cyclopropane was used only for the induction of anesthesia and was gradually superseded by more safe anesthetics. Cyclopropane works by blocking NMDA and AMPA receptors and activating K2P channels, kainate ion channels and glycine receptors at clinical concentrations.

Approval Year

PubMed

PubMed

TitleDatePubMed
Reactivities of methylenetriangulanes and spirocyclopropanated bicyclopropylidenes toward bromine. Relative stabilities of spirocyclopropanated versus methyl-substituted bromonium ions.
2002-06-14
Design, synthesis, and evaluation of matrix metalloprotease inhibitors bearing cyclopropane-derived peptidomimetics as P1' and P2' replacements.
2002-06-14
Catalytic asymmetric cyclopropanation using bridged dirhodium tetraprolinates on solid support.
2002-06-13
Ti(II)-mediated conversion of alpha-heterosubstituted (O, N, S) nitriles to functionalized cyclopropylamines. Effect of chelation on the cyclopropanation step.
2002-05-31
Effect of geminal substitution on the strain energy of dioxiranes. Origin of the low ring strain of dimethyldioxirane.
2002-05-31
Watson-Crick base-pairing properties of tricyclo-DNA.
2002-05-29
Synthesis, crystal structure, and H/D exchange of the inside protonated form of the cage imine 4,8,12-triaza-1-azoniatricyclo[6.6.3.2(4,12)]nonadec-1(15)-ene. A model for proton transfer through an aliphatic membrane.
2002-05-08
Substitution mode of the amide fragment in some new N-[omega-[4-(2-methoxyphenyl)piperazin-1-yl]alkyl]pyrid-2(1H)-ones and their 5-HT1A/5-HT2A activity.
2002-05-07
Zirconium-mediated intramolecular ester transfer reaction: synthesis of alpha-substituted gamma-aminobutyric acid (GABA) derivatives.
2002-05-02
Coupling of isoprenoid triflates with organoboron nucleophiles: synthesis and biological evaluation of geranylgeranyl diphosphate analogues.
2002-05
Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A.
2002-04-25
Synthesis, structures, and strain energies of dispirophosphiranes. Comparisons with dispirocyclopropanes.
2002-04-19
Directed evolution to generate cycloartenol synthase mutants that produce lanosterol.
2002-04-18
Stereoselective cyclopropanation by cyclocopolymerization of butadiene.
2002-04-10
Hydroxy-directed diastereoselective installation of a methyl group on indalone models and spiroketal potential precursors for the bafilomycin A(1) C15-C25 subunit.
2002-04-05
Ab initio direct dynamics study of cyclopropyl radical ring-opening.
2002-04-03
2-Chloro N(6)-methyl-(N)-methanocarba-2'-deoxyadenosine-3',5'-bisphosphate is a selective high affinity P2Y(1) receptor antagonist.
2002-04
Phospholipid modifications in bacteria.
2002-04
Crystal structures of mycolic acid cyclopropane synthases from Mycobacterium tuberculosis.
2002-03-29
Use of chirally modified zeolites and crystals in photochemical asymmetric synthesis.
2002-03-27
In search of high stereocontrol for the construction of cis-disubstituted cyclopropane compounds. Total synthesis of a cyclopropane-configured urea-PETT analogue that is a HIV-1 reverse transcriptase inhibitor.
2002-03-21
Development of versatile cis- and trans-dicarbon-substituted chiral cyclopropane units: synthesis of (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes and their enantiomers as conformationally restricted analogues of histamine.
2002-03-08
Domino reactions of amidines with methyl 2-chloro-2-cyclopropylideneacetate as an efficient access to cyclobutene-annelated pyrimidinones.
2002-03-07
Delineating novel metabolic pathways of DPC 963, a non-nucleoside reverse transcriptase inhibitor, in rats. Characterization of glutathione conjugates of postulated oxirene and benzoquinone imine intermediates by LC/MS and LC/NMR.
2002-03
SAR studies of 3-cyclopropanecarbonyloxy-2-cyclohexen-1-one as inhibitors of 4-hydroxyphenylpyruvate dioxygenase.
2002-03
Metalation of 2-chloromethyl-2-oxazolines: synthesis of 1,2,3-tris(oxazolinyl)cyclopropanes and derivatives.
2002-02-08
X-ray structure analysis and the intervalent electron transfer in organic mixed-valence crystals with bridged aromatic cation radicals.
2002-02-06
Thermal decomposition and isomerization of cis-permethrin and beta-cypermethrin in the solid phase.
2002-02
Stereochemistry of two new polyfunctionalized gem-dihalocyclopropanes.
2002-02
Chromium- and tungsten-triggered valence isomerism of cis-1-acyl-2-ethynylcyclopropanes via [3,3]sigmatropy of (2-acylcyclopropyl)vinylidene-metal intermediates.
2002-01-30
Insights into regioselective oxy (-O-) and imino (-NH-) group insertions of 3-nortricyclanone.
2002-01-25
Reaction of a double bond of zirconacyclopentadienes: formation of 1,2,3,5-tetrasubstituted benzenes via the C-C bond cleavage.
2002-01-23
Observation of conformation-specific pathways in the photodissociation of 1-iodopropane ions.
2002-01-17
Calorimetric and structural studies of 1,2,3-trisubstituted cyclopropanes as conformationally constrained peptide inhibitors of Src SH2 domain binding.
2002-01-16
DNA-binding properties and cytotoxicity of extended aromatic bisamidines in breast cancer MCF-7 cells.
2002-01-15
Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species.
2002-01-12
Highly enantioselective oxidation of cis-cyclopropylmethanols to corresponding aldehydes catalyzed by chloroperoxidase.
2002-01-11
A density functional theory investigation of the Simmons-Smith cyclopropanation reaction: examination of the insertion reaction of zinc into the C-I bond of CH(2)I(2) and subsequent cyclopropanation reactions.
2002-01-11
Methanocarba modification of uracil and adenine nucleotides: high potency of Northern ring conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but not P2Y6 receptors.
2002-01-03
The Escherichia coli ftsK1 mutation attenuates the induction of sigma(S)-dependent genes upon transition to stationary phase.
2002-01-02
Studies of silyl-accelerated 1,5-hydrogen migrations in vinylcyclopropanes.
2001-12-28
Fats and fatty acids as growth factors for Lactobacillus delbrueckii.
2001-12
Temperature- and growth-phase-regulated changes in lipid fatty acid structures of psychrotolerant groundwater Proteobacteria.
2001-12
Synthesis of cyclobutane analogues of the antiviral cyclopropane nucleoside A-5021.
2001-12
Mechanistic investigations on the reaction between 1,2-dioxines and bulky stabilized phosphorus ylides: an efficient route to closely related cyclopropane stereoisomers.
2001-11-30
Conformational analysis of nevirapine, a non-nucleoside HIV-1 reverse transcriptase inhibitor, based on quantum mechanical calculations.
2001-11
Diastereo- and enantioselective cyclopropanation with chromium fischer carbene complexes: alkenyl oxazolines as useful achiral and chiral substrates.
2001-10-31
How persistent is cyclopropyl upon nucleophilic substitution, and is frontside displacement possible? A model study.
2001-10-19
Dissection of a flavoenzyme active site: the reaction catalyzed by cholesterol oxidase.
2001-10
Distance indices and their hyper-counterparts: intercorrelation and use in the structure-property modeling.
2001
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:57:09 GMT 2025
Edited
by admin
on Wed Apr 02 09:57:09 GMT 2025
Record UNII
99TB643425
Record Status Validated (UNII)
Record Version
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Name Type Language
CYCLOPROPANE [HSDB]
Preferred Name English
Cyclopropane
HSDB   INN   MART.   MI   USP   WHO-DD  
INN  
Official Name English
cyclopropane [INN]
Common Name English
CYCLOPROPANE [MART.]
Common Name English
CYCLOPROPANE [USP IMPURITY]
Common Name English
CYCLOPROPANE [MI]
Common Name English
Cyclopropane [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID4058786
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
WIKIPEDIA
CYCLOPROPANE
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
MERCK INDEX
m4014
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
200-847-8
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PRIMARY
HSDB
812
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
INN
1395
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PRIMARY
EVMPD
SUB06861MIG
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
FDA UNII
99TB643425
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
NCI_THESAURUS
C81404
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
SMS_ID
100000083775
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
DRUG BANK
DB13984
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
CAS
75-19-4
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
CHEBI
30365
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
MESH
C030797
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL1796999
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
PUBCHEM
6351
Created by admin on Wed Apr 02 09:57:09 GMT 2025 , Edited by admin on Wed Apr 02 09:57:09 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY