thumb left 120px The typical structure of cyclopentane is the envelope conformation. Industrial usage Cyclopentane is used in the manufacture of chemical synthesis synthetic resin s and rubber adhesive ... cyclopentane MAC lubricants because of their extremely low volatility. ref name pennzane http ... via a process known as catalytic reforming . For example, 2 methylbutane can be reformed into cyclopentane ... ca Ciclopent cs Cyklopentan de Cyclopentan el es Ciclopentano fr Cyclopentane it Ciclopentano ... more details
Summary Envelope structure of cyclopentane . Created by User Isopropyl Isopropyl using XDrawchem. Licensing PD self date October 2006 Copy to Wikimedia Commons bot Fbot Orphan image ... more details
DISPLAYTITLE C sub 5 sub H sub 10 sub The molecular formula C sub 5 sub H sub 10 sub may refer to Cyclopentane 1,2 Dimethylcyclopropane 2 Methyl 2 butene Methylcyclobutane Pentene MolFormDisambig Short pages monitor This long comment was added to the page to prevent it being listed on Special Shortpages. It and the accompanying monitoring template were generated via Template Longcomment. Please do not remove the monitor template without removing the comment as well. el C5H10 fr C5H10 nl C5H10 ... more details
refimprove date January 2012 Psychotropic alkylamines are alkylamines that share the critical property of not containing an aromatic nucleus, but are still biologically active. While many of these molecules are stimulants some of them natural , others are antiviral, have competitive NMDA antagonist activity, or are nicotinic receptor antagonists. class wikitable Compound Core Other N Substituent Pharmacology Neramexane Cyclohexyl 1,3,3,5,5 Pentamethyl 1 NH2 NMDA antagonist Amantadine adamantane 1 NH2 Antiviral drug antiviral , NMDA antagonist, catecholamine releaser, cholinergic Memantine 3,5 DiMe NMDA antagonist Rimantadine CH3CH NH2 Antiviral drug antiviral Cyclopentamine cyclopentane n propyl 2 NHMe Sympathomimetic vasoconstrictor Propylhexedrine cyclohexane Methylhexanamine n hexane 4 methyl 2 NH2 Tuaminoheptane n heptane 2 NH2 Octodrine 6 methyl Mecamylamine norbornane 1 exo 2,2 trimethyl 1 endo NHMe nicotinic antagonist Alkenylamines Isometheptene Alkanolamines Heptaminol Category Amines pharm stub ... more details
Chembox ImageFile Spirodecane ifa.png ImageSize 100px IUPACName spiro 4.5 decane OtherNames Section1 Chembox Identifiers CASNo 176 63 6 PubChem 135982 ChemSpiderID 119760 SMILES C2CCC1 CCCCC1 C2 InChI InChI 1S C10H18 c1 2 6 10 7 3 1 8 4 5 9 10 h1 9H2 Section2 Chembox Properties Formula C sub 10 sub H sub 18 sub MolarMass 138.25 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Spirodecane is a chemical compound . It features a cyclohexane ring bound directly to a cyclopentane ring. Azaspirodecane is an structural analogue analogue in which the cyclohexane group has been replaced with a piperidine . See also Azaspirodecane organic compound stub Category Spiro compounds ... more details
Image Iridomyrmecin chemical structure.png thumb Chemical structure of iridomyrmecin Iridoids are a class of secondary metabolite s found in a wide variety of plants and in some animals. They are monoterpene s biosynthesized from isoprene and they are often intermediates in the biosynthesis of alkaloid s. Chemically, the iridoids usually consist of a cyclopentane ring fused to a six membered oxygen heterocycle. The chemical structure is exemplified by iridomyrmecin , a defensive chemical produced by the Iridomyrmex genus, for which iridoids are named. Cleavage of a bond in the cyclopentane ring gives rise to a subclass known as seco iridoids, such as amarogentin . Iridoids are typically found in plants as glycoside s, most often bound to glucose . Iridoids are found in many medicinal plants and may be responsible for some of their pharmaceutical activities. Isolated and purified, iridoids exhibit a wide range of bioactivities including cardiovascular, antihepatotoxic, choleretic, hypoglycemic, analgesic, anti inflammatory, antimutagenic, antispasmodic, antitumor, antiviral, immunomodulator, and purgative activities. ref Didna, B., Debnath, S., Harigaya, Y. Naturally Occurring Iridoids. A Review, Part 1. Chem. Pharm. Bull. 55 2 159 222 2007 . ref ref Tundis R, Loizzo MR, Menichini F, Statti GA, Menichini F. Biological and pharmacological activities of iridoids recent developments. Mini Rev Med Chem . 2008 Apr 8 4 399 420. ref The iridoids are produced by plants primarily as a defense against herbivores or against infection by microorganisms. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste. Aucubin and catalpol are two of the most common iridoids in the plant kingdom. Iridoids are prevalent in the plant subclass Asteridae , such as Ericaceae , Loganiaceae , Gentianacae , Rubiaceae , Verbenaceae , Lamiaceae , Oleaceae , Plantaginaceae , Scrophulariaceae , Valerianaceae , and Menyanthaceae . References references Category Iridoi ... more details
Expand Greek 1,2 date March 2010 chembox verifiedrevid 410949157 ImageFileL1 1 2 DimethylCyclopropane.png ImageSizeL1 120px ImageFileR1 Dimethylcyclopropane.png ImageSizeR1 120px IUPACName 1,2 Dimethylcyclopropane OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 92890 InChI 1 C5H10 c1 4 3 5 4 2 h4 5H,3H2,1 2H3 InChIKey VKJLDXGFBJBTRQ UHFFFAOYAK StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H10 c1 4 3 5 4 2 h4 5H,3H2,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey VKJLDXGFBJBTRQ UHFFFAOYSA N CASNo Ref cascite ?? ?? CASNo 2511 95 7 PubChem 102832 SMILES CC1CC1C RTECS Section2 Chembox Properties C 5 H 10 Appearance Density MeltingPt BoilingPtC Solubility pKa pKb Section3 Chembox Hazards MainHazards FlashPt Autoignition Section8 Chembox Related OtherCpds cyclopropane , cyclopentane 1,2 Dimethylcyclopropane is a cycloalkane consisting of a cyclopropane ring and two methyl groups. It has two geometric isomers E and Z , depending on the position of its two methyl groups. As with other cyclopropanes, ring tension results in a relatively unstable compound. 1,2 Dimethylcyclopropane is 1 of 10 structural isomer s cycloalkane s and aliphatic alkene s which share the general formula of C sub 5 sub H sub 10 sub . The others being cyclopentane , methylcyclobutane , 1,1 dimethylcyclopropane , ethylcyclopropane , 1 pentene , 2 pentene , 2 methyl 1 butene , 3 methyl 1 butene , and 2 Methyl 2 butene 2 methyl 2 butene . See also Alkyl cycloalkane DEFAULTSORT Dimethylcyclopropane, 1,2 Category Cyclopropanes Category Hydrocarbons el 1,2 nl 1,2 dimethylcyclopropaan ... more details
DISPLAYTITLE TEX sub 86 sub TEX sub 86 sub is a paleothermometer based on the composition of membrane lipid s of the marine plankton picoplankton Crenarchaeota . Wuchter et al. 2004 found that the number of cyclopentane rings in Crenarchaeota membrane lipids changes linearly with temperature in order to regulate membrane fluidity. The sedimentary composition of such lipids which exist as far back as the early Cretaceous can therefore be used to reconstruct average temperatures experienced by the plankton, and thus of the past water column. This method was used by Jenkyns et al. 2004 to show that average sea surface temperatures in the currently ice covered Arctic Ocean 80 degrees N were as high as 15 degrees Celsius in the late Cretaceous . References Schouten, S., Hopmans, E.C., Schefus, E., and Sinninghe Damste, 2002, Distributional variation in marine crenarchaeotal membrane lipids a new tool for reconstructing ancient sea water temperatures? Earth and Planetary Science Letters, v. 204, p. 265 274. Wuchter, C., Schouten, S., Coolen, M., Damste, J. 2004 Temperature dependent variation in the distribution of tetraether membrane lipids of marine Crenarchaeota Implications for TEX86 paleothermometry. PALEOCEANOGRAPHY 19 PA4028 Jenkyns, H., Forster, A., Schouten, S., Damste, J 2004 High temperatures in the Late Cretaceous Arctic Ocean. Nature 432 888 891. Category Paleoclimatology ca TEX86 es TEX 86 ... more details
planar cyclopentane the C C C bond angles would be 108 degrees, very close to the measure of the tetrahedral angle. Actual cyclopentane molecules are puckered, but this changes only the bond angles ... more details
Image Cyclopropane.png thumb 150px right Cyclopropane is the smallest alicyclic compound. An alicyclic compound is an organic compound that is both Aliphatic compound aliphatic and cyclic compound cyclic . They contain one or more all carbon rings which may be either saturation chemistry saturated or unsaturated, but do not have aromaticity aromatic character. ref GoldBookRef title Alicyclic compounds file A00216 year 1995 ref Alicyclic compounds may or may not have aliphatic side chains attached. The simplest alicyclic compounds are the monocyclic cycloalkane s cyclopropane , cyclobutane , cyclopentane , cyclohexane , cycloheptane , cyclooctane , cyclononane , cyclodecane , cycloundecane , cyclododecane , and so on. Bicyclic molecule Bicyclic alkanes include bicycloundecane and decalin . Polycyclic compound Polycyclic alkanes include cubane , basketane , and housane . Spiro compound s have two or more rings that are connected through only one carbon atom. An exocyclic group is always shown outside the ring structure, take for instance the exocyclic double bond on the left Image Exocyclic.png 200px Left exocyclic double bond Right regular double bond br style clear both See for an example isotoluene . The placement of double bonds in many alicyclic compounds can be predicted with Bredt s rule . The mode of ring closing in the formation of many alicyclic compounds can be predicted by Baldwin s rules . Cycloalkenes Image Cyclohexene.png thumb right Cyclohexene is an alicyclic compound with a double bond. Monocyclic cycloalkene s are cyclopropene , cyclobutene , cyclopentene , cyclohexene , cycloheptene , cyclooctene , and so on. Bicyclic alkenes include norbornene and norbornadiene . References references Category Organic compounds Category Organic chemistry ar ca Compost alic clic de Alicyclische Verbindungen et Alits klilised hendid el fa fr Compos alicyclique he hu Aliciklusos vegy let ... more details
Unreferenced date December 2009 Image Alkyl cycloalkane.png thumb Methylcyclopropane , the simplest alkyl cycloalkane. Alkyl cycloalkanes are chemical compound s with an alkyl group with a single ring of carbon s to which hydrogen s are attached according to the formula C sub n sub H sub 2n sub . They are named analogously to their normal alkane counterpart of the same carbon count methylcyclopropane , methylcyclobutane , methylcyclopentane , methylcyclohexane , etc. Methylcycloalkanes are classed into compounds with small, normal and bigger cycloalcanes, where cyclopropane and cyclopbutane are the small ones, cyclopentane , cyclohexane , cycloheptane are the normal ones and the rest are the bigger ones. TOC Nomenclature The naming of polycyclic alkanes is more complex, with the base name indicating the number of carbons in the ring system, a prefix indicating the number of rings e.g., bicyclo , and a numeric prefix before that indicating the number of carbons in each part of each ring, exclusive of vertices. For instance, a bicyclooctane which consists of a six member ring and a four member ring, which share two adjacent carbon atoms which form a shared edge, is 4.2.0 bicyclooctane. That part of the six member ring, exclusive of the shared edge has 4 carbons. That part of the four member ring, exclusive of the shared edge, has 2 carbons. The edge itself, exclusive of the two vertices that define it, has 0 carbons. Reactions The normal and the bigger alkylcycloalkanes are very stable like alkanes and their reactions cf. radicalic chain reactions are like alkanes. The small alkylcycloalkanes particularly alkylcyclopropane has a lower stability due to the Baeyer tension . They react similar to alkenes , though they don t react with the EA cf. electrophilic addition , but with the SN2 cf. nucleophilic substitution reaction mechanism. These reactions are both ring opening reactions and Cleavage crystal cleavage reactions. Typical compound The typical compound of the gro ... more details
chembox verifiedrevid 443547741 Reference ref http www.sigmaaldrich.com catalog search ProductDetail FLUKA 07621 Cycloleucine at Sigma Aldrich ref ImageFile Cycloleucin.svg ImageSize 150px IUPACName 1 Amino 1 cyclopentanecarboxylic acid OtherNames 1 Aminocyclopentanecarboxylic acid Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 2798 KEGG Ref keggcite correct kegg KEGG C03969 InChI 1 C6H11NO2 c7 6 5 8 9 3 1 2 4 6 h1 4,7H2, H,8,9 InChIKey NILQLFBWTXNUOE UHFFFAOYAN SMILES1 O C O C1 N CCCC1 ChEMBL Ref ebicite correct EBI ChEMBL 295830 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C6H11NO2 c7 6 5 8 9 3 1 2 4 6 h1 4,7H2, H,8,9 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey NILQLFBWTXNUOE UHFFFAOYSA N CASNo 52 52 8 PubChem 2901 DrugBank Ref drugbankcite correct drugbank DrugBank DB04620 SMILES C1CCC C1 C O O N Section2 Chembox Properties Formula C sub 6 sub H sub 11 sub NO sub 2 sub MolarMass 129.16 g mol Appearance Density MeltingPtC 320 BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Cycloleucine is a non proteinogenic amino acid . It could be classified as a cyclic derivate of norleucine , having two hydrogen atoms less. Leading structure is a cyclopentane ring. The carbon atom is not a stereocenter. Cycloleucine is a non metabolisable amino acid and is a specific and reversible Enzyme inhibitor inhibitor of nucleic acid methylation , and as such is widely used in biochemical experiments. ref cite journal author M Caboche and JP Bachellerie title RNA methylation and control of eukaryotic RNA biosynthesis. Effects of cycloleucine, a specific inhibitor of methylation, on ribosomal RNA maturation journal European Journal of Biochemistry volume 74 pages 19 29 year 1977 doi 10.1111 j.1432 1033.1977.tb11362.x pmid 856572 issue 1 ref . References reflist Category Amino acids organic compound stub biochem stub de Cycloleucin ... more details
chembox verifiedrevid 464385786 Reference ref Beilstein database Beilstein . 5, IV , 451 ref Name Sabinene ImageFile Sabinene.png ImageSize 120px ImageName Sabinene IUPACName 4 methylene 1 1 methylethyl bicyclo 3.1.0 hexane Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 17769 PubChem 18818 KEGG Ref keggcite correct kegg KEGG C16777 InChI 1 C10H16 c1 7 2 10 5 4 8 3 9 10 6 10 h7,9H,3 6H2,1 2H3 InChIKey NDVASEGYNIMXJL UHFFFAOYAW ChEMBL Ref ebicite correct EBI ChEMBL 452687 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C10H16 c1 7 2 10 5 4 8 3 9 10 6 10 h7,9H,3 6H2,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey NDVASEGYNIMXJL UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 3387 41 5 CASOther br 2009 00 9 br 10408 16 9 ChEBI Ref ebicite correct EBI ChEBI 50027 SMILES C C2C1CC1 C C C CC2 Section2 Chembox Properties Formula C sub 10 sub H sub 16 sub MolarMass 136.23 g mol Density 0.844 g mL at 20 C g cm sup 3 sup MeltingPt BoilingPt 163 164 C Sabinene is a natural bicyclic terpene monoterpene with the molecular formula C sub 10 sub H sub 16 sub . It is isolated from the essential oil s of a variety of plants including holm oak Quercus ilex and Norway spruce Picea abies . It has a strained ring system with cyclopentane ring fused to a cyclopropane ring. Sabinene is one of the chemical compounds that contributes to the spiciness of black pepper and is a major constituent of carrot seed oil. It also occurs in tea tree oil at a low concentration. It is also present in the essential oil obtained from nutmeg. ref cite pmid 5615546 ref See also Thujene , a double bond isomer of sabinene References reflist Category Hydrocarbons Category Alkenes Category Monoterpenes Category Cyclopropanes hydrocarbon stub de Sabinen fr Sabin ne it Sabinene hu Szabin n nl Sabineen ru ... more details
chembox verifiedrevid 443705168 ImageFileL1 1,2 dithiolane 2D skeletal.png ImageSizeL1 75px ImageFileR1 Dithiolane13d.png ImageSizeR1 100px ImageFileL2 1,3 dithiolane 2D skeletal.png ImageSizeL2 75px ImageFileR2 Dithiolane23d.png ImageSizeR2 100px IUPACName Dithiolane OtherNames 1,2 dithiolane, 1,3 dithiolane Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 71377 InChI 1 C3H6S2 c1 2 4 5 3 1 h1 3H2 InChIKey MUZIZEZCKKMZRT UHFFFAOYAH StdInChI Ref stdinchicite correct chemspider StdInChI 1S C3H6S2 c1 2 4 5 3 1 h1 3H2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey MUZIZEZCKKMZRT UHFFFAOYSA N CASNo PubChem 79045 ChEBI Ref ebicite correct EBI ChEBI 38226 SMILES S1SCCC1 Section2 Chembox Properties Formula C sub 3 sub H sub 6 sub S sub 2 sub MolarMass Appearance Density MeltingPt BoilingPt Solubility pKa pKb Section3 Chembox Hazards MainHazards FlashPt Autoignition Section8 Chembox Related OtherCpds 1,2 Ethanedithiol A dithiolane is a sulfur heterocyclic compound heterocycle derived from cyclopentane by replacing two methylene CH sub 2 sub groups with thioether groups. The parent compounds are 1,2 dithiolane and 1,3 dithiolane . 1,2 Dithiolanes, such as lipoic acid , are cyclic disulfides . 1,3 Dithiolanes are important as protecting group s for carbonyl compounds, since they are inert to a wide range of conditions. Reacting a carbonyl group with 1,2 ethanedithiol converts it to a 1,3 dithiolane, as detailed below. Image Carbonyl protection with ethanedithiol 2D.png center 400px Protecting a carbonyl group by converting it to a 1,3 dithiolane, using 1,2 ethanedithiol External links http www.organic chemistry.org protectivegroups carbonyl 1,3 dithiolanes.htm 1,3 Dithiolane Reactions Category Dithiolanes ja zh ... more details
Drugbox verifiedrevid 413289634 IUPAC name 6aR,10aR 3 1 hexylcyclopentyl 6,6,9 trimethyl 6a,7,10,10a tetrahydrobenzo c chromen 1 ol image AMG 36.png width 240 Clinical data tradename legal status routes of administration Pharmacokinetic data metabolism elimination half life excretion Identifiers CAS number PubChem 10982174 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 9157375 ChEMBL Ref ebicite correct EBI ChEMBL 108868 Chemical data C 27 H 40 O 2 molecular weight 396.604 g mol smiles CC2 C Oc1cc C4 CCCCCC CCCC4 cc O c1C C3 C2CC C3C StdInChI Ref stdinchicite correct chemspider StdInChI 1S C27H40O2 c1 5 6 7 8 13 27 14 9 10 15 27 20 17 23 28 25 21 16 19 2 11 12 22 21 26 3,4 29 24 25 18 20 h11,17 18,21 22,28H,5 10,12 16H2,1 4H3 t21 ,22 m1 s1 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey FONCHEGPDSYFCG FGZHOGPDSA N AMG 36 is an analgesic drug which is a cannabinoid agonist . It is a derivative of 8 THC substituted with a cyclopentane group on the 3 position side chain. AMG 36 is a potent agonist at both Cannabinoid receptor 1 CB sub 1 sub and Cannabinoid receptor 2 CB sub 2 sub with moderate selectivity for CB sub 1 sub , with a Dissociation constant K sub i sub of 0.4nM at CB sub 1 sub vs 1.9nM at CB sub 2 sub . ref Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A. Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1 . Journal of Medicinal Chemistry . 2003 Jul 17 46 15 3221 9. PMID 12852753 ref ref Papahatjis DP, Nahmias VR, Nikas SP, Andreou T, Alapafuja SO, Tsotinis A, Guo J, Fan P, Makriyannis A. C1 cycloalkyl side chain pharmacophore in tetrahydrocannabinols. Journal of Medicinal Chemistry . 2007 Aug 23 50 17 4048 60. PMID 17672444 ref References references cannabinoids cannabinoid stub Category Cannabinoids Category Benzochromenes Category Phenols ... more details
Drugbox verifiedrevid 424795310 IUPAC name methyl 2 cyclopentyl 2 3,4 dichlorophenyl acetate image O 2172 structure.png width 220 Clinical data tradename routes of administration Identifiers CAS number ATC suffix PubChem 11778793 Chemical data C 14 H 16 Cl 2 O 2 molecular weight 287.181 smiles Clc1ccc cc1Cl C C O OC C2CCCC2 O 2172 is a drug developed by Organix Inc, which acts as a stimulant and potent dopamine reuptake inhibitor . It is an analogue of methylphenidate where the phenyl ring has had a 3,4 dichloro substitution added, and the piperidine ring has been replaced by cyclopentane . It is around 1 3 the potency of methylphenidate , demonstrating that even with the important binding group of the nitrogen lone pair removed entirely, selective dopamine transporter DAT binding and reuptake inhibition is still possible. ref Meltzer PC, Wang P, Blundell P, Madras BK. Synthesis and evaluation of dopamine and serotonin transporter inhibition by oxacyclic and carbacyclic analogues of methylphenidate . Journal of Medicinal Chemistry . 2003 Apr 10 46 8 1538 45. PMID 12672255 ref ref Runyon SP, Carroll FI. Dopamine transporter ligands recent developments and therapeutic potential. Current Topics in Medicinal Chemistry . 2006 6 17 1825 43. PMID 17017960 ref See also Tropoxane References reflist Stimulants Dopaminergics Category Dopamine reuptake inhibitors Category Stimulants Category Organochlorides Category Methyl esters nervous system drug stub ... more details
chembox verifiedrevid 355909758 ImageFile Isocomene.png ImageSize IUPACName 3 aS ,5 aS ,8 aR 1,3 a ,4,5 a tetramethyl 1,2,3,3 a ,5 a ,6,7,8 octahydrocyclopenta c pentalene OtherNames Section1 Chembox Identifiers CASNo PubChem 188113 SMILES CC1 C C 3 C CCC C 32 C H C CC C 12C InChI 1 C15H24 c1 11 6 9 14 4 12 2 10 13 3 7 5 8 15 11,13 14 h10 11H,5 9H2,1 4H3 t11 ,13 ,14 ,15 m1 s1 Section2 Chembox Properties C 15 H 24 MolarMass Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Isocomene is a naturally occurring sesqui terpene first isolated from the rayless golden rod Isocoma wrightii , from which it derives its name. Its unusual structure consisting of three fused cyclopentane rings was first described by Zalkow et al. in 1977. The first total synthesis of isocomene was published by M.C. Pirrung in 1979. The key steps are a Photocatalysis photocatalyzed Intramolecular reaction intramolecular 2 2 cycloaddition reaction followed by a rearrangement reaction which forms three contiguous Chirality chemistry chiral centers. ref name Nicolaou cite book title Classics in Total Synthesis last Nicolaou first K. C. authorlink K. C. Nicolaou coauthors E. J. Sorensen year 1996 publisher VCH location Weinheim, Germany isbn 3 527 29284 5 page 221 pages url accessdate ref References reflist Total synthesis of . . isocomene Michael C. Pirrung Journal of the American Chemical Society 1979 101 23 , 7130 7131 organic compound stub Category Sesquiterpenes Category Pentalenes ... more details
Drugbox Watchedfields changed verifiedrevid 437204019 IUPAC name RS 1 cyclopentyl N methyl propan 2 amine image Cyclopentamine.svg width 260 imagename 1 1 mixture racemate drug name Cyclopentamine Clinical data tradename pregnancy category legal status Uncontrolled routes of administration Inhalation Pharmacokinetic data bioavailability metabolism elimination half life excretion Identifiers CAS number 102 45 4 ATC prefix R01 ATC suffix AA02 PubChem 7608 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 7326 UNII Ref fdacite correct FDA UNII WB9Q6M8O60 KEGG Ref keggcite correct kegg KEGG D07370 ChEMBL Ref ebicite correct EBI ChEMBL 329203 Chemical data C 9 H 19 N 1 molecular weight 141.254 smiles N C C CC1CCCC1 C InChI 1 C9H19N c1 8 10 2 7 9 5 3 4 6 9 h8 10H,3 7H2,1 2H3 InChIKey HFXKQSZZZPGLKQ UHFFFAOYAZ StdInChI Ref stdinchicite correct chemspider StdInChI 1S C9H19N c1 8 10 2 7 9 5 3 4 6 9 h8 10H,3 7H2,1 2H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey HFXKQSZZZPGLKQ UHFFFAOYSA N synonyms N , dimethyl cyclopenaneethylamine boiling point 171 Cyclopentamine Clopane , Cyclonarol , Cyclosal , Cyklosan , Nazett , Sinos is a sympathomimetic Amine Aliphatic amines alkylamine , classified as a vasoconstrictor . Cyclopentamine was indication medicine indicated in the past as an Over the counter drug over the counter OTC medication for use as a human nose nasal decongestant , notably in Europe and Australia , but has now been largely discontinuation discontinued possibly due to the availability, effectiveness, and safety of a structurally similar drug, propylhexedrine . Citation needed date October 2009 Chemistry Cyclopentamine is the cyclopentane Homology chemistry homologue of propylhexedrine , differing only in terms of the contracted ring size of a cyclopentane, containing one CH2 unit less than the cyclohexyl group. In terms of the acyclic part of the molecule, both cyclopentamine and propylhexedrine are directly synonymous with methamphetam ... more details
Image Decahydronaphthalene.png thumb 150px right Decalin , also known as bicyclo 4.4.0 decane Image Norbornane 2D skeletal.png thumb 150px right Norbornane , also known as bicyclo 2.2.1 heptane Image Spiro 2.2 pentane.svg thumb 150px right spiro 2.2 pentane, a spirocyclic molecule A bicyclic molecule is a molecule that features two fused Cyclic compound rings . Bicyclic molecules occur widely in organic compound organic and inorganic compound s. Fusion of the rings can occur in three ways Across a bond between two atoms for example, decalin also known as bicyclo 4.4.0 decane , has a C C bond shared between two cyclohexane rings Across a sequence of atoms bridgehead for example, norbornane also known as bicyclo 2.2.1 heptane , can be viewed as a pair of cyclopentane rings that share three of the five carbon atoms At a single atom spirocyclic , forming a spiro compound Singly fused rings are the most common, and spiro rings are the least common. Bridges A bridge is an unbranched chain of atom s or an atom or a covalent bond connecting two bridgeheads in a polycyclic compound . The main bridge is a bridge that connects the two main bridgeheads. A secondary bridge is any bridge not included in the main ring or the main bridge. An independent secondary bridge links bridgeheads that are part of the main ring or main bridge. A dependent secondary bridge links at least one bridgehead that is part of a secondary bridge. Nomenclature Bicyclic molecules have a strict IUPAC nomenclature of organic chemistry nomenclature . ref http www.acdlabs.com iupac nomenclature 79 r79 163.htm IUPAC nomenclature for bicyclics ref On its simplest level the parent hydrocarbon is the equivalent open carbon alkane . For bridged compounds, the Prefix linguistics prefix bicyclo is added, followed by, between brackets, separated by periods, and, in descending order, the number of carbon atoms between each of the bridgeheads. For example in bicyclo 2.2.1 heptane the carbon frame contains a total of ... more details
chembox verifiedrevid 412509081 Reference ref Merck Index , 11th Edition, 2748 . ref ref http www.inchem.org documents icsc icsc eics0427.htm Cyclopentanone at inchem.org ref Name Cyclopentanone ImageFile Cyclopentanone.png ImageSize 80px ImageName Cyclopentanone IUPACName cyclopentanone OtherNames ketocyclopentane br adipic ketone Section1 Chembox Identifiers UNII 220W81TN3S ChEBI 16486 SMILES C1CCC O C1 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 8141 PubChem 8452 KEGG Ref keggcite correct kegg KEGG C00557 InChI 1 C5H8O c6 5 3 1 2 4 5 h1 4H2 InChIKey BGTOWKSIORTVQH UHFFFAOYAP ChEMBL Ref ebicite correct EBI ChEMBL 18620 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H8O c6 5 3 1 2 4 5 h1 4H2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey BGTOWKSIORTVQH UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 120 92 3 RTECS GY4725000 Section2 Chembox Properties Formula C sub 5 sub H sub 8 sub O MolarMass 84.12 g mol Appearance clear, colorless liquid Density 0.95 g cm sup 3 sup , liquid Solubility Slightly soluble MeltingPtC 58.2 BoilingPtC 130.6 Viscosity Section3 Chembox Structure Dipole Section7 Chembox Hazards ExternalMSDS http siri.org msds mf cards file 0427.html Cyclopentanone MainHazards FlashPt 26 C RPhrases SPhrases Section8 Chembox Related Function ketone s OtherFunctn cyclohexanone br 2 Pentanone 2 pentanone br 3 pentanone OtherCpds cyclopropane Cyclopentanone is a colorless liquid organic compound with a peppermint like odor. It is a cyclic ketone , structurally similar to cyclopentane , consisting of a five membered ring containing a ketone functional group. Safety The compound is stable, but flammable the vapour is denser than air by 2.3 times. Cyclopentanone is harmful if swallowed, inhaled or absorbed through the skin. It is also irritant to the human skin skin and respiratory system , and a severe irritant to the human eye eye s. Use Cyclopentanone is commonly used as a thinner for various epoxies used in MEMS f ... more details
The leucines are primarily the four isomer ic amino acid s leucine , isoleucine , tert Leucine tert leucine and norleucine . Being compared with the four butanol s, they could be classified as butyl substituted glycine s they represent all four possible variations. Leucine and isoleucine belong to the proteinogenic amino acid s the others are non natural. Including the stereoisomers, six further isomers could be added small D small leucine, small D small isoleucine, small L small allo isoleucine, small D small allo isoleucine, small D small tert leucine and small D small norleucine., Cycloleucine could be classified as a cyclic derivate of norleucine . With a cyclopentane ring, it has two hydrogen atoms less and thus is not an isomer. The carbon atom is not a stereocenter. center class wikitable centered style text align center font size 90 class hintergrundfarbe6 align center colspan 6 Leucines class hintergrundfarbe5 align left Name small L small Leucine small L small Isoleucine small L small tert Leucine tert Leucine Terleucine small L small Norleucine Cycloleucine class hintergrundfarbe5 align left Other names 2 Amino 4 methylpentanoic acid, br Isobutylglycine 2 Amino 3 methylpentanoic acid, br sec Butylglycine 2 Amino 3,3 dimethylbutanoic acid, br tert Butylglycine 2 Amino hexanoic acid, br n Butylglycine 1 Amino cyclopentane 1 carboxylic acid br class hintergrundfarbe5 align left Structure Image L Leucin L Leucine.svg 150px Image L Isoleucin L Isoleucine.svg 150px Image L tert Leucine.svg 110px Image L Norleucin.svg 175px Image Cycloleucin.svg 105px class hintergrundfarbe5 align left CAS number 61 90 5 73 32 5 20859 02 3 327 57 1 52 52 8 class hintergrundfarbe5 align left PubChem PubChem 6106 PubChem 791 PubChem 164608 PubChem 21236 PubChem 2901 class hintergrundfarbe5 align left Molecular formula colspan 4 C sub 6 sub H sub 13 sub NO sub 2 sub C sub 6 sub H sub 11 sub NO sub 2 sub class hintergrundfarbe5 align left Molar mass colspan 4 131.18 g mol 12 ... more details
chembox verifiedrevid 443389140 ImageFile Nepetalactone chemical structure.png ImageSize 140px IUPACName 4,7 dimethyl 5,6,7,7a tetrahydro cyclopenta c pyran 1 4aH one IUPACName hidden yes OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 141747 InChI1 1 C10H14O2 c1 6 3 4 8 7 2 5 12 10 11 9 6 8 h5 6,8 9H,3 4H2,1 2H3 t6 ,8 ,9 m0 s1 InChIKey1 ZDKZHVNKFOXMND NBEYISGCBC StdInChI Ref stdinchicite correct chemspider StdInChI 1S C10H14O2 c1 6 3 4 8 7 2 5 12 10 11 9 6 8 h5 6,8 9H,3 4H2,1 2H3 t6 ,8 ,9 m0 s1 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey ZDKZHVNKFOXMND NBEYISGCSA N CASNo 490 10 8 PubChem 161367 SMILES O C1O C C C H 2CC C H C H 12 C C InChI 1 C10H14O2 c1 6 3 4 8 7 2 5 12 10 11 9 6 8 h5 6,8 9H,3 4H2,1 2H3 Section2 Chembox Properties C 10 H 14 O 2 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Nepetalactone is an organic compound , first isolated from the plant Nepeta catnip Nepeta cataria , which acts as a cat attractant . Nepetalactone is bicyclic terpenoid , i.e., it is a ten carbon compound derived from isoprene with two fused rings, a cyclopentane and a lactone . The structure and the effects of the compound are similar to those of valepotriate s. A number of isomer s of nepetalactone are known. Nepetalactone was first reported in 1941 after it was isolated by steam distillation of catnip. ref cite journal author Samuel M. McElvain , R. D. Bright and P. R. Johnson title The Constituents of the Volatile Oil of Catnip. I. Nepetalic Acid, Nepetalactone and Related Compounds year 1941 journal J. Am. Chem. Soc. volume 63 issue 6 pages 1558 1563 doi 10.1021 ja01851a019 ref The compound is also present in the wood of tartarian honeysuckle Lonicera tatarica , shavings of which are often used in cat toys. Effects on animals 4a ,7 ,7a Nepetalactone is the active chemical in Nepeta cataria and has a characteristic effect on cat s. Around 50 o ... more details
See also List of UN Numbers UN 1101 to UN 1200 class wikitable width 140px UN Number Class Proper Shipping Name UN 1104 3 Amyl acetate s UN 1105 3 Pentanol s UN 1106 3 Amylamine s UN 1107 3 Amyl chloride s UN 1108 3 1 Pentene n amylene UN 1109 3 Amyl formate s UN 1110 3 n Amyl methyl ketone UN 1111 3 Amyl mercaptan s UN 1112 3 Amyl nitrate UN 1113 3 Amyl nitrite s UN 1114 3 Benzene UN 1120 2 Butanol s UN 1123 3 Butyl acetate s UN 1125 3 n Butylamine UN 1126 3 1 Bromobutane UN 1127 3 Chlorobutane s UN 1128 3 n Butyl formate UN 1129 3 Butyraldehyde UN 1130 3 Camphor oil UN 1131 3 Carbon disulfide UN 1133 3 Adhesive s, containing a flammable liquid UN 1134 3 Chlorobenzene UN 1135 6.1 Ethylene chlorohydrin UN 1136 3 Coal tar distillates, flammable UN 1139 3 Coating solution includes surface treatments or coatings used for industrial or other purposes such as vehicle undercoating, drum or barrel lining UN 1143 6.1 Crotonaldehyde , stabilized UN 1144 3 Crotonylene UN 1145 3 Cyclohexane UN 1146 3 Cyclopentane UN 1147 3 Decahydronaphthalene UN 1148 3 Diacetone alcohol UN 1149 3 Dibutyl ether s UN 1150 3 1,2 Dichloroethylene UN 1152 3 Dichloropentane s UN 1153 3 Ethylene glycol diethyl ether UN 1154 3 Diethylamine UN 1155 3 Diethyl ether or Ethyl ether UN 1156 3 Diethyl ketone UN 1157 3 Diisobutyl ketone UN 1158 3 Diisopropylamine UN 1159 3 Diisopropyl ether UN 1160 3 Dimethylamine solution UN 1161 3 Dimethyl carbonate UN 1162 3 Dimethyldichlorosilane UN 1163 6.1 Dimethylhydrazine , unsymmetrical UN 1164 3 Dimethyl sulfide UN 1165 3 Dioxane UN 1166 3 Dioxolane UN 1167 3 Divinyl ether , inhibited UN 1169 3 Extracts, aromatic, liquid UN 1170 3 Ethanol Ethyl alcohol or Ethanol solution Ethyl alcohol solution UN 1171 3 Ethylene glycol monoethyl ether UN 1172 3 Ethylene glycol monoethyl ether acetate UN 1173 3 Ethyl acetate UN 1175 3 Ethylbenzene UN 1176 3 Ethyl borate UN 1177 3 2 Ethylbutyl acetate UN 1178 3 2 Ethylbutyraldehyde UN 1179 3 Ethyl butyl ether UN 1180 3 Ethyl butyra ... more details
Chembox Verifiedfields changed Watchedfields changed verifiedrevid 410048505 ImageFile Cyclopentanepentone 2D.png ImageFile Ref chemboximage correct ?? ImageSize 121 ImageName Skeletal formula of cyclopentanepentone SystematicName Cyclopentane 1,2,3,4,5 pentone ref Cite web url http pubchem.ncbi.nlm.nih.gov summary summary.cgi?cid 12305030&loc ec rcs title CID 12305030 PubChem Public Chemical Database work The PubChem Project location USA publisher National Center for Biotechnology Information ref OtherNames Leuconic acid Section1 Chembox Identifiers CASNo Ref cascite correct ?? CASNo 3617 57 0 PubChem 12305030 PubChem Ref Pubchemcite correct pubchem ChemSpiderID 16788087 ChemSpiderID Ref chemspidercite changed chemspider SMILES O C1C O C O C O C1 O StdInChI 1S C5O5 c6 1 2 7 4 9 5 10 3 1 8 StdInChI Ref stdinchicite changed chemspider StdInChIKey YVVXMBHAKNKELS UHFFFAOYSA N StdInChIKey Ref stdinchicite changed chemspider Section2 Chembox Properties C 5 O 5 ExactMass 139.974573110 g mol sup 1 sup Cyclopentanepentone , also known as leuconic acid , is a hypothetical organic compound with formula C sub 5 sub O sub 5 sub , the fivefold ketone of cyclopentane . It would be an oxide of carbon an oxocarbon , indeed a polymer pentamer of carbon monoxide . As of 2000, the compound had yet to be synthesized in bulk, but there have been reports of trace synthesis. ref name rubin cite journal doi 10.1021 cr960079j pmid 11749259 title The Chemistry of Vicinal Polycarbonyl Compounds year 2000 last1 Rubin first1 Mordecai B. last2 Gleiter first2 Rolf journal Chemical Reviews volume 100 issue 3 pages 1121 ref ref name seitz cite journal title Oxocarbons and pseudooxocarbons author Gunther Seitz coauthors Peter Imming journal Chemical Reviews year 1992 volume 92 issue 6 pages 1227 1260 doi 10.1021 cr00014a004 ref ref cite journal title Mass spectrometric studies of the oxocarbons CnOn n 3 6 author Detlef Schr der, Helmut Schwarz , Suresh Dua, Stephen J. Blanksby and John H. Bowie doi ... more details
Chembox verifiedrevid 399890226 ImageFile Decahydroxycyclopentane.png ImageSize 150px IUPACName cyclopentane 1,1,2,2,3,3,4,4,5,5 decaol OtherNames decahydroxycyclopentane Section1 Chembox Identifiers InChI 1 C5H10O10 c6 1 7 2 8,9 4 12,13 5 14,15 3 1,10 11 h6 15H InChIKey DYYJKUCFQJABMU UHFFFAOYAO SMILES1 C1 C C C C1 O O O O O O O O O O StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H10O10 c6 1 7 2 8,9 4 12,13 5 14,15 3 1,10 11 h6 15H StdInChIKey Ref stdinchicite correct chemspider StdInChIKey DYYJKUCFQJABMU UHFFFAOYSA N CASNo 595 03 9 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 21477367 PubChem SMILES OC1 O C O O C O O C O O C O 1O Section2 Chembox Properties C 5 H 10 O 10 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Decahydroxycyclopentane is an organic compound with formula C sub 5 sub O sub 10 sub H sub 10 sub or C sub 5 sub OH sub 10 sub . It is a fivefold geminal diol on a cyclopentane backbone. The compound can be regarded as the fivefold hydrate of cyclopentanepentone . Indeed, the product referred to in the literature and trade as cyclopentanepentone pentahydrate C sub 5 sub O sub 5 sub 5H sub 2 sub O is now believed to be the decahydroxycyclopentane. ref cite journal title Oxocarbons and pseudooxocarbons author Gunther Seitz coauthors Peter Imming journal Chemical Reviews year 1992 volume 92 issue 6 pages 1227 1260 doi 10.1021 cr00014a004 url http admin.pubs.acs.org doi pdf 10.1021 cr00014a004 ref ref Willis B. Person and Dale G. Williams 1957 , Infrared spectra and the structures of leuconic acid and triquinoyl . J. Phys. Chem., 61 7 , 1017 1018. DOI 10.1021 j150553a047 ref The compound was synthetized by Heinrich Will in 1861, although for a long time it was believed to be a hydrate of C sub 5 sub O sub 5 sub . It can be prepared by oxidation of croconic acid C sub 5 sub O sub 3 sub OH sub 2 sub with nitric acid . ref cite journal journal Justus Liebigs Annalen der ... more details
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