br Pyrroline one double bond br Pyrrolizidine two pentagonal rings Pyrrolidine , also known as tetrahydropyrrole ... http www.thegoodscentscompany.com data rw1009391.html Pyrrolidine , The Good Scents Company ref Pyrrolidine is found naturally in the leaves of tobacco and carrot . The pyrrolidine ring structure ... e.g. piracetam , aniracetam . A pyrrolidine ring is the central structure of the amino acid s proline and hydroxyproline . In organic chemistry, pyrrolidine is used to activate ketone s and aldehyde s toward ... msds 96268.htm Pyrrolidine MSDS References references Category Pyrrolidines Category Solvents ar de Pyrrolidin fa fr Pyrrolidine id Pirolidina it Pirrolidina lv Pirolid ns nl Pyrrolidine ... more details
Chembox Watchedfields changed verifiedrevid 312823060 ImageFile Pyrrolidine dithiocarbamate.png ImageSize 150px IUPACName Pyrrolidine 1 carbodithioic acid OtherNames Pyrrolidinedithiocarbamate 1 Pyrrolidinecarbodithioic acid Pyrrolidine dithiocarbamic acid Section1 Chembox Identifiers Abbreviations PDTC CASNo 25769 03 3 PubChem 65351 SMILES S C S N1CCCC1 Section2 Chembox Properties C 5 H 9 N 1 S 2 Appearance Density 1.264 g cm sup 3 sup MeltingPt BoilingPt 199.7 C 760mmHg Solubility Section3 Chembox Hazards MainHazards FlashPt 74.6 C Autoignition Pyrrolidine dithiocarbamate PDTC is a chemical compound with the molecular formula C sub 5 sub H sub 9 sub NS sub 2 sub . PDTC and its salt chemistry salts , such as ammonium pyrrolidinecarbodithioate, are used for a variety of biochemical applications including metal chelation , induction of G1 phase cell cycle arrest, ref cite journal doi 10.1002 jcp.10728 pmid 14603533 year 2004 month Feb last1 Moon first1 SK last2 Jung first2 SY last3 Choi first3 YH last4 Lee first4 YC last5 Patterson first5 C last6 Kim first6 CH title PDTC, metal chelating compound, induces G1 phase cell cycle arrest in vascular smooth muscle cells through inducing p21Cip1 expression involvement of p38 mitogen activated protein kinase volume 198 issue 2 pages 310 23 issn 0021 9541 journal Journal of cellular physiology ref and preventing induction of nitric oxide synthase . ref http www.sigmaaldrich.com catalog ProductDetail.do?lang en&N4 P8765 SIGMA&N5 SEARCH CONCAT PNO BRAND KEY&F SPEC Ammonium pyrrolidinedithiocarbamate at Sigma Aldrich ref References reflist Category Pyrrolidines Category Dithiocarbamates fa ... more details
DISPLAYTITLE C sub 4 sub H sub 9 sub N The molecular formula C sub 4 sub H sub 9 sub N may refer to Pyrrolidine azolidine Cyclobutylamine cyclobutanamine 2,2 Dimethylaziridine 1,2 Dimethylaziridine MolFormDisambig el C4H9N ... more details
Chembox ImageFile Phenylethylpyrrolidine.png ImageSize IUPACName 1 2 phenylethyl pyrrolidine OtherNames Section1 Chembox Identifiers CASNo 6273 83 2 PubChem 411735 ChemSpiderID 364511 SMILES c1c cccc1 CCN2CCCC2 InChI InChI 1S C12H17N c1 2 6 12 7 3 1 8 11 13 9 4 5 10 13 h1 3,6 7H,4 5,8 11H2 Section2 Chembox Properties Formula C sub 12 sub H sub 17 sub N MolarMass 175.27 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition 1 2 Phenylethyl pyrrolidine PEP is a chemical compound . It is an structural analog analogue of 2 phenylethylamine where the amine has been replaced by a pyrrolidine functional group ring . It is the base chemical structure for a series of stimulant drug s, including div style moz column count 3 column count 3 webkit column count 3 alpha Pyrrolidinobutiophenone PBP alpha Pyrrolidinopropiophenone PPP alpha Pyrrolidinopentiophenone PVP 3 ,4 Methylenedioxy pyrrolidinobutiophenone MDPBP 3 ,4 Methylenedioxy pyrrolidinopropiophenone MDPPP 3,4 Methylenedioxypyrovalerone MDPV 4 Methoxy pyrrolidinopropiophenone MOPPP 4 Methyl pyrrolidinobutiophenone MPBP 4 Methyl pyrrolidinohexiophenone MPHP 4 Methyl pyrrolidinopropiophenone MPPP Naphyrone Prolintane Pyrovalerone div All of these compounds differ from PEP in that the alpha carbon is extended and a ketone is attached to the beta carbon with the exception of prolintane , among other modifications. It is unknown whether PEP itself has any stimulant properties, but it can be considered likely. Citation needed date April 2010 See also Phenethylamine Amphetamine Cathinone Stimulants Phenethylamines Category Pyrrolidines Category Stimulants organic compound stub fa ... more details
Drugbox verifiedrevid 444076183 IUPAC name 1 2 E 4 4 chlorophenyl 3 phenylbut 2 en 1 yl pyrrolidine image pyrrobutamine.png Clinical data tradename pregnancy category legal status routes of administration Pharmacokinetic data bioavailability protein bound metabolism elimination half life excretion Identifiers CAS number 91 82 7 ATC prefix R06 ATC suffix AX08 PubChem 5284614 UNII Ref fdacite correct FDA UNII VE6KP18S8X Chemical data C 20 H 22 Cl 1 N 1 molecular weight 311.848 g mol Pyrrobutamine is an antihistamine and anticholinergic . References Reflist 2 Cholinergics Histaminergics Category Pyrrolidines Category Alkenes Category Organochlorides Category H1 receptor antagonists Category Anticholinergics respiratory system drug stub th ... more details
The Leimgruber Batcho indole synthesis is a series of organic reaction s that produce indole s from o nitro toluene s 1 . Ref BatchoPatent Ref Batch1985 Ref Clark1984 The first step is the formation of an enamine 2 using N,N dimethylformamide dimethyl acetal and pyrrolidine . Ref Maehr1981 The desired indole 3 is then formed in a second step by Redox reductive cyclisation. Image Leimgruber Batcho Indole Scheme.png center 500px The Leimgruber Batcho indole synthesis In the above scheme, the reductive cyclisation is effected by Raney nickel and hydrazine . palladium on carbon Palladium on carbon and hydrogen , stannous chloride , sodium dithionite Ref Garcia1974 , or iron in acetic acid Ref Ponticello1979 are also effective reducing agent s. Reaction mechanism In the initial enamine formation, dimethylamine a gas is displaced by pyrrolidine from the dimethylformamide dimethylacetal, producing a more reactive reagent . The mildly acidic hydrogens of the methyl group in the nitrotoluene can be deprotonation deprotonated under the basic conditions, and the resultant carbanion attacks to produce the enamine shown, with loss of methanol . The sequence can be also be performed without the pyrrolidine, via the N,N dimethyl enamine, though reaction times may be much longer in some cases. In the second step the nitro compound nitro group is reduced to NH sub 2 sub using hydrogen and a Raney nickel catalyst, followed by cyclisation then elimination reaction elimination of the pyrrolidine. The hydrogen is often generated in situ by the spontaneous decomposition of hydrazine hydrate to Hydrogen H sub 2 sub and Nitrogen N sub 2 sub in the presence of the nickel. The reaction is a good example of a reaction that was widely used in industry before any procedures were published in the mainstream scientific literature. Many indoles are Pharmacology pharmacalogically active , so a good indole synthesis is important for the pharmaceutical industry. The process has become a popular alter ... more details
chembox verifiedrevid 374532111 Name PolyDADMAC ImageFile PolyDADMAC.png ImageSize 150px IUPACName SystematicName OtherNames Poly dimethyldiallylammonium chloride Section1 Chembox Identifiers Abbreviations ChemSpiderID NA CASNo 26062 79 3 EINECS EINECSCASNO Section2 Chembox Properties Formula C sub 8 sub H sub 16 sub NCl sub n sub MolarMass variable Appearance Density MeltingPt Melting notes BoilingPt Boiling notes Solubility soluble SolubleOther Solvent LogP VaporPressure HenryConstant AtmosphericOHRateConstant pKa pKb Section7 Chembox Hazards ExternalMSDS EUClass EUIndex MainHazards NFPA H NFPA F NFPA R NFPA O RPhrases R52 53 SPhrases RSPhrases FlashPt Autoignition ExploLimits LD50 PEL Section8 Chembox Related OtherAnions OtherCations OtherFunctn Function OtherCpds Polydiallyldimethylammonium chloride , or shortened polyDADMAC is a homopolymer of diallyldimethylammonium chloride DADMAC . The molecular weight of polyDADMAC is typically in the range of hundreds of thousands of grams per mole, and even up to a million for some products. PolyDADMAC is usually delivered as a liquid concentrate having a solids level in the range of 10 to 50 . It is a high charge density cationic polymer . The charge density makes it well suited for flocculation . Synthesis The monomer DADMAC is formed by reacting two equivalents of allyl chloride with dimethylamine . PolyDADMAC is then organic synthesis synthesized by radical polymerization of DADMAC with an organic peroxide used as a catalyst . Two polymeric structures are possible when polymerizing DADMAC N substituted piperidine structure or N substituted pyrrolidine structure. The pyrrolidine structure is favored. ref Citation last John first Wilson last2 et al. publication date 2002 title Structure and Properties of PolyDADMAC for Water Purification url http academic.sun.ac.za unesco Conferences Conference2002 JohnP.pdf ref Image Polymerization PolyDADMAC.jpg 250px thumb left Polymerization of PolyDADMAC shown as favoured pyrrolidi ... more details
Infobox protein family Symbol Collagen Name Collagen triple helix image 1K6F Crystal Structure Of The Collagen Triple Helix Model Pro Pro Gly103 04.png width caption Model of a collagen helix. ref name pmid11790836 cite journal author Berisio R, Vitagliano L, Mazzarella L, Zagari A title Crystal structure of the collagen triple helix model Pro Pro Gly 10 3 journal Protein Sci. volume 11 issue 2 pages 262 70 year 2002 month February pmid 11790836 pmc 2373432 doi 10.1110 ps.32602 url ref Pfam PF01391 InterPro IPR008160 SMART PROSITE SCOP 1a9a TCDB OPM family OPM protein PDB PDB2 1q7d , PDB2 1rj7 , PDB2 1rj8 Image Fibers of Collagen Type I TEM.jpg thumb Transmission electron microscopy TEM image of collagen fibres. In collagen , the collagen helix , or type 2 helix, is a major shape in secondary structure . It consists of a triple helix made of the repetitious amino acid sequence glycine X Y, where X and Y are frequently proline or hydroxyproline . ref cite journal author Bhattacharjee A, Bansal M title Collagen structure the Madras triple helix and the current scenario journal IUBMB Life volume 57 issue 3 pages 161 72 year 2005 month March pmid 16036578 doi 10.1080 15216540500090710 ref Each of the three chains is stabilized by the steric repulsion due to the pyrrolidine rings of proline and hydroxyproline residue chemistry residue s. The pyrrolidine rings keep out of each other s way when the polypeptide chain assumes this extended helical form, which is much more open than the tightly coiled form of the alpha helix . The three chains are hydrogen bond ed to each other. The Hydrogen bonding Bonding hydrogen bond donors are the peptide NH groups of glycine residues. The Hydrogen bonding Bonding hydrogen bond acceptors are the CO groups of residues on the other chains. The OH group of hydroxyproline also participates in hydrogen bonding. The rise of the collagen helix superhelix is 2.9 0.29 nm per residue. References reflist Protein secondary structure DEFAULTSO ... more details
chembox verifiedrevid ImageFile Phthalprop.svg ImageSize 200px IUPACName 2 1 oxo 1 phenylpropan 2 yl isoindole 1,3 dione OtherNames Section1 Chembox Identifiers ChemSpiderID Ref ChemSpiderID UNII Ref fdacite correct FDA UNII KEGG Ref keggcite correct kegg KEGG InChI 1 C12H7Cl3O2 c13 7 1 3 11 9 15 5 7 17 12 4 2 8 14 6 10 12 16 h1 6,16H InChIKey XEFQLINVKFYRCS UHFFFAOYAS ChEMBL Ref ebicite correct EBI ChEMBL StdInChI Ref stdinchicite correct chemspider StdInChI 1S C12H7Cl3O2 c13 7 1 3 11 9 15 5 7 17 12 4 2 8 14 6 10 12 16 h1 6,16H StdInChIKey Ref stdinchicite correct chemspider StdInChIKey XEFQLINVKFYRCS UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 19437 20 8 PubChem SMILES Clc2cc Cl ccc2Oc1ccc Cl cc1O Section2 Chembox Properties C 17 H 13 N 1 O 3 Appearance Density 1.304 g cm sup 3 sup MeltingPt 87 88 C BoilingPt 447.2 C Solubility Section3 Chembox Hazards MainHazards FlashPt 204.4 C Autoignition Phthalimidopropiophenone is a chemical intermediate used in the synthesis of cathinone . It has been found to be sold on the illicit market as a designer drug controlled substance analogue , but little is currently known about its pharmacology or toxicology. ref Camilleri A, Johnston MR, Brennan M, Davis S, Caldicott DG. Chemical analysis of four capsules containing the controlled substance analogues 4 methylmethcathinone, 2 fluoromethamphetamine, alpha phthalimidopropiophenone and N ethylcathinone. Forensic Science International . 2010 Jan 13. DOI 10.1016 j.forsciint.2009.12.048 PMID 20074881 ref Phthalimidopropiophenone is not an active stimulant, but is believed to be potentially capable of acting as a prodrug for cathinone when ingested, as similar N substituted cathinone derivatives have been encountered by law enforcement, and were found to form cathinone in vivo by initial hydroxylation of the pyrrolidine ring followed by subsequent dehydrogenation to the corresponding lactam, then by double dealkylation of the pyrrolidine ring to form the primary amine. ref Sprin ... more details
name is 1 3 Methyl 4 morpholino 2,2 diphenylbutyryl pyrrolidine, and its molecular formula C sub ... of several different structural features i at the 1 amide group only the pyrrolidine and dimethylamide substituents were active, with pyrrolidine being more potent ii the alkyl chain was more ... the dextro isomer was more active iii while morpholine, dimethylamine, pyrrolidine and piperidine ... rings reduces activity. So dextromoramide, with a pyrrolidine ring on the 1 amide position, a dextro ... more details
distinguish Cope rearrangement The Cope reaction or Cope elimination , developed by Arthur C. Cope , is an elimination reaction of an amine oxide to form an alkene and a hydroxylamine . The reaction mechanism involves an intramolecular 5 membered cyclic transition state , ref 1 leading to a syn elimination syn elimination product. This organic reaction gives the same result as the Hofmann elimination , ref 1 but the base chemistry base is a part of the leaving group . The amine oxide is prepared by organic oxidation oxidation of the corresponding amine with an oxidant such as mCPBA m CPBA . The actual elimination just requires heat. Image CopeReaction.png center 554px Cope reaction An application is a synthesis of methylenecyclohexane ref Organic Syntheses , Coll. Vol. 4, p.612 1963 Vol. 39, p.40 1959 . http orgsynth.org orgsyn pdfs CV4P0612.pdf Link ref File MethyleneCyclohexaneByCopeReaction.svg 389 synthesis of methylenecyclohexane Piperidine s are resistant to an intramolecular Cope reaction ref JerryMarch ref ref Amine Oxides. VIII. Medium sized Cyclic Olefins from Amine Oxides and Quaternary Ammonium Hydroxides Arthur C. Cope, Engelbert Ciganek, Charles F. Howell, Edward E. Schweizer J. Am. Chem. Soc. , 1960 , 82 17 , pp 4663 4669 DOI 10.1021 ja01502a053 ref ref Amine Oxides. VII. The Thermal Decomposition of the N Oxides of N Methylazacycloalkanes Arthur C. Cope, Norman A. LeBel J. Am. Chem. Soc. 1960 82 17 4656 4662. DOI 10.1021 ja01502a052 ref but with pyrrolidine and with rings of size 7 and larger, the reaction product is an Saturation chemistry unsaturated hydroxyl amine. This result demonstrates the geometric constraints of a 5 membered cyclic transition state . File CopeReactionJACS82 4656.svg 261px intramolecular Cope reaction References Reflist DEFAULTSORT Cope Reaction Category Elimination reactions Category Name reactions de Cope Eliminierung nl Cope eliminatie ja zh ... more details
chembox Name Cuscohygrine IUPACName 1,3 bis 1 methylpyrrolidin 2 yl propan 2 one ImageFile Cuscohygrine hr.png ImageSize 150px ImageName Chemical structure of cuscohygrine Section1 Chembox Identifiers ChemSpiderID 389876 InChI 1 C13H24N2O c1 14 7 3 5 11 14 9 13 16 10 12 6 4 8 15 12 2 h11 12H,3 10H2,1 2H3 InChIKey ZEBIACKKLGVLFZ UHFFFAOYAQ CASNo 454 14 8 KEGG C06521 SMILES O C CC1N C CCC1 CC2N C CCC2 Section2 Chembox Properties Formula C sub 13 sub H sub 24 sub N sub 2 sub O MolarMass 224.34 g mol MeltingPt BoilingPt Density Cuscohygrine is a pyrrolidine alkaloid found in coca . It can be extracted from plants of the family Solanaceae as well, including Atropa belladonna deadly nightshade , Datura inoxia and Datura stramonium jimson weed . Cuscohygrine usually comes with other, more potent alkaloids like atropine or cocaine . Cuscohygrine along with the related metabolite hygrine was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca leaves also known as Cusco leaves . Cuscohygrine is an oil, which can be distilled without decomposition only in vacuum. It is easily soluble in water and forms an optically inactive crystalline hydrate C sub 13 sub H sub 24 sub N sub 2 sub O 3H sub 2 sub O, which melts at 40 41 C. References cite web title PubChem Substance Summary url http pubchem.ncbi.nlm.nih.gov summary summary.cgi?sid 8752 accessdate July 14, 2005 cite web title USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. nowiki Online Database nowiki National Germplasm Resources Laboratory, Beltsville, Maryland. url http sun.ars grin.gov 8080 npgspub xsql duke chemdisp.xsql?chemical CUSCOHYGRINE accessdate July 14, 2005 cite book author Dr. Ame Pictet title The Vegetable Alkaloids. With particular reference to their chemical constitution location London publisher Chapman & Hall year 1904 id Category Alkaloids Category Ketones Category Pyrrolidines fa fr Cuscohygrine fi Kuskohygriini ... more details
chembox verifiedrevid 443865442 Name Hygrine IUPACName R 1 1 methylpyrrolidin 2 yl propan 2 one ImageFile Hygrine hr.png ImageName Chemical structure of hygrine Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 389762 PubChem 440933 KEGG Ref keggcite correct kegg KEGG C06179 InChI 1 C8H15NO c1 7 10 6 8 4 3 5 9 8 2 h8H,3 6H2,1 2H3 t8 m1 s1 InChIKey ADKXZIOQKHHDNQ MRVPVSSYBT StdInChI Ref stdinchicite correct chemspider StdInChI 1S C8H15NO c1 7 10 6 8 4 3 5 9 8 2 h8H,3 6H2,1 2H3 t8 m1 s1 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey ADKXZIOQKHHDNQ MRVPVSSYSA N CASNo Ref cascite correct ?? CASNo 496 49 1 ChEBI Ref ebicite correct EBI ChEBI 46750 SMILES CC O C C H 1CCCN1C Section2 Chembox Properties Formula C sub 8 sub H sub 15 sub NO MolarMass 141.21 g mol MeltingPt BoilingPt 193 195 C Density Hygrine is a pyrrolidine alkaloid , found mainly in coca leaves 0.2 . It was first isolated by Carl Liebermann in 1889 along with a related compound cuscohygrine as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor. References cite book author Dr. Ame Pictet title The Vegetable Alkaloids. With particular reference to their chemical constitution publisher Chapman & Hall location London year 1904 id cite encyclopedia encyclopedia Webster s Revised Unabridged Dictionary year 1913 edition ? article Hygrine cite web title USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. nowiki Online Database nowiki National Germplasm Resources Laboratory, Beltsville, Maryland. url http sun.ars grin.gov 8080 npgspub xsql duke chemdisp.xsql?chemical HYGRINE accessdate July 15, 2005 Category Alkaloids Category Ketones Category Pyrrolidines bg es Higrina fr Hygrine ja pt Higrina ru sr Higrin fi Hygriini sv Hygrin ... more details
Drugbox verifiedrevid 444089733 IUPAC name 1 1 phenylcyclohexyl pyrrolidine image Rolicyclidine.svg width 125px Clinical data tradename legal status Schedule I Class A Identifiers CAS number 2201 39 0 ATC prefix none PubChem 62436 DrugBank Ref drugbankcite correct drugbank DrugBank DB01549 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 56218 UNII Ref fdacite correct FDA UNII 183O9O9JE3 ChEBI Ref ebicite correct EBI ChEBI 60805 Chemical data C 16 H 23 N 1 molecular weight 229.361 g mol smiles c1ccccc1C3 N2CCCC2 CCCCC3 InChI 1 C16H23N c1 3 9 15 10 4 1 16 11 5 2 6 12 16 17 13 7 8 14 17 h1,3 4,9 10H,2,5 8,11 14H2 InChIKey FYOWWXMGDATDQY UHFFFAOYAQ StdInChI Ref stdinchicite correct chemspider StdInChI 1S C16H23N c1 3 9 15 10 4 1 16 11 5 2 6 12 16 17 13 7 8 14 17 h1,3 4,9 10H,2,5 8,11 14H2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey FYOWWXMGDATDQY UHFFFAOYSA N Rolicyclidine PCPy is a Dissociative drug dissociative anesthesia anesthetic drug with hallucinogen ic and sedative effects. It is similar in effects to phencyclidine but is slightly less potent and has less stimulant effects ref Kalir A, Edery H, Pelah Z, Balderman D, Porath G. 1 Phenylcycloalkylamine derivatives. II. Synthesis and pharmacological activity. Journal of Medicinal Chemistry. 1969. 12 3 473 477 ref instead producing a sedative effect described as being somewhat similar to a barbiturate , but with additional PCP like dissociative, anaesthetic and hallucinogenic effects. ref DEA Microgram Bulletin, 8, 143, 1975 ref Due to its similarity in effects to PCP, PCPy was placed into the Schedule I list of illegal drugs in the 1970s, although it has never been widely abused and is now little known. See also Arylcyclohexylamine References Reflist 2 General anesthetics Depressants Hallucinogens Dopaminergics Glutamatergics Category Dissociative drugs Category Pyrrolidines nervous system drug stub pl Rolicyklidyna ... more details
Pyrrolines , also known under the name dihydropyrroles , are three different heterocyclic compound heterocyclic organic chemistry organic chemical compound s that differ in the position of the double bond . Pyrrolines are formally derived from the aromaticity aromate pyrrole by hydrogenation . 1 Pyrroline is a cyclic imine , whereas 2 pyrroline and 3 pyrroline are cyclic amine s. align center valign top Image 1 pyrroline chemical structure.png 50px Image 2 pyrroline chemical structure.png 50px Image 3 pyrroline chemical structure.png 50px align center style padding 0 1em 0 1em 1 Pyrroline style padding 0 1em 0 1em 2 Pyrroline style padding 0 1em 0 1em 3 Pyrroline Substituted pyrrolines 2 Acetyl 1 pyrroline , an aroma compound with a white bread like smell Thienamycin , a beta lactam antibiotic MTSL , a chemical used for certain NMR experiments Pyrrolysine , an unusual proteinogenic amino acid 1 Pyrroline 5 carboxylic acid , a biosynthetic metabolite Porphyrin , consisting of two alternating pairs of pyrrol and pyrroline connected via methine CH bridges See also Pyrrole , the aromatic analog with two double bonds Pyrrolidine , the fully saturated analog without double bonds External links http www.ebi.ac.uk chebi searchId.do?chebiId CHEBI 3A23763 Pyrroline , http www.ebi.ac.uk chebi searchId.do?chebiId CHEBI 3A19092 1 pyrroline , http www.ebi.ac.uk chebi searchId.do?chebiId CHEBI 32986 2 pyrroline , and http www.ebi.ac.uk chebi searchId.do?chebiId CHEBI 3A20198 3 pyrroline at EMBL EBI Amine stub Category Pyrrolines de Pyrroline fr Azoline id Pirolina lv Pirol ns ja pl Piroliny ru sr Pirolin sv Pyrrolin zh ... more details
Drugbox verifiedrevid 449870661 IUPAC name 1 1 methyl 3,3 di 2 thienylprop 2 en 1 yl pyrrolidine image Pyrrolidinylthiambutene.png width 180 Clinical data tradename pregnancy AU pregnancy US pregnancy category legal AU legal CA legal US legal status routes of administration Pharmacokinetic data bioavailability protein bound metabolism elimination half life excretion Identifiers CAS number ATC prefix none ATC suffix PubChem Chemical data C 16 H 19 N 1 S 2 molecular weight 289.458 g mol smiles C2CCCN2C C C C c1sccc1 c3sccc3 melting point 167 melting high 169 Pyrrolidinylthiambutene is an opioid analgesic drug from the thiambutene family with around 3 4 of the potency of morphine . ref Adamson DW, Green AF. A new series of analgesics. Nature . 1950 Jan 21 165 4186 122. DOI 10.1038 165122a0 PMID 15409854 ref ref Adamson DW, Duffin WM, Green AF. Dithienylbutylamines as analgesics. Nature . 1951 Jan 27 167 4239 153 4. DOI 10.1038 167153b0 PMID 14806409 ref ref Green AF. Analgesic and other properties of 3 3 dithienylalkenylamines. British Journal of Pharmacology and Chemotherapy . 1953 Mar 8 1 2 9. PMID 13066683 ref It would be considered an illegal Federal Analog Act controlled substance analogue in some countries such as the USA, Australia and New Zealand, but is legal in countries not possessing a controlled substances analog act equivalent. References references Opioids Category Opioids Category Thiophenes Category Pyrrolidines Category Mu opioid agonists analgesic stub ... more details
Drugbox IUPAC name 1 2 4 6 methoxy 2 phenyl 3,4 dihydronaphthalen 1 yl phenoxy ethyl pyrrolidine image Nafoxidine.png Clinical data tradename Identifiers CAS number 1845 11 0 ATC prefix none PubChem 4416 ChemSpiderID 4263 UNII Ref fdacite correct FDA UNII 4RIY10WM82 ChEMBL 28211 Chemical data C 28 H 31 N 1 O 2 molecular weight 425.562 g mol smiles COC1 CC2 C C C1 C C CC2 C3 CC CC C3 C4 CC C C C4 OCCN5CCCC5 Nafoxidine U 11,000A is a non steroid al anti estrogen ic drug that has been investigated to treat advanced breast cancer. ref cite doi 10.1002 mpo.2950040207 ref It is structurally related to tamoxifen . The drug is one of a series of similar structures invented by Dan Lednicer at Upjohn . An earlier compound known as http www.sciencebase.com serendipity and science.html U 11,555 is related to Nafoxidine was found to cause photosensitivity in human volunteers as for example does psoralen . File U 11,555 image.png thumb left See D. Lednicer, J.C. Babcock, P.E. Marlatt, S.C. Lyster, G.W. Duncan, J.Med.Chem., 8, 52 1965 . for details. ref http dx.doi.org 10.1021 2Fjm00325a013 ref Synthesis The synthesis depicted is more modern, but also see Lasofoxifene for an earlier synthesis. File Nafoxidine synthesis.png 500px Cameron, C. O. Dasilva Jardine, P. A. Rosati, R. L. 1996, US Patent 5,552,412 . References Reflist Category Experimental cancer drugs Category Pyrrolidines Category Phenol ethers Category Dilines Chemotherapeutic agents Estrogenics antineoplastic drug stub ... more details
Drugbox verifiedrevid 413650153 IUPAC name 3S 3 2,3 dihydro 5 methoxy 1H inden 4 yl oxy pyrrolidine image Org37684 structure.png width 240 Clinical data tradename pregnancy category legal status Uncontrolled routes of administration Pharmacokinetic data bioavailability protein bound metabolism elimination half life excretion Identifiers CAS number ATC prefix ATC suffix PubChem 9794656 IUPHAR ligand 171 Chemical data C 14 H 19 N 1 O 2 molecular weight 233.305 g mol smiles COc1ccc2CCCc2c1OC3CNCC3 Org 37,684 is a drug developed by Organon International Organon , which acts as a potency pharmacology potent and functional selectivity selective agonist for the 5 HT2 receptor 5 HT sub 2 sub receptor biochemistry receptor family, with highest affinity pharmacology affinity at 5 HT2C receptor 5 HT sub 2C sub and lowest at 5 HT2B receptor 5 HT sub 2B sub subtypes. ref cite doi 10.1081 SCC 100104420 ref ref Knight AR, Misra A, Quirk K, Benwell K, Revell D, Kennett G, Bickerdike M. Pharmacological characterisation of the agonist radioligand binding site of 5 HT 2A , 5 HT 2B and 5 HT 2C receptors. Naunyn Schmiedebergs Archives of Pharmacology . 2004 370 114 123. DOI 10.1007 s00210 004 0951 4 PMID 15322733 ref It has anorectic effects in animal studies and has been researched as a potential weight loss drug for use in humans. ref Schreiber R, De Vry J. Role of 5 hT2C receptors in the hypophagic effect of m CPP, ORG 37684 and CP 94,253 in the rat. Progress in Neuropsychopharmacology and Biological Psychiatry . 2002 Apr 26 3 441 9. PMID 11999893 ref See also Org 12,962 References Reflist 2 Anorectics Serotonergics Category Serotonin receptor agonists Category Indanes Category Phenol ethers Category Pyrrolidines gastrointestinal drug stub ... more details
Drugbox verifiedrevid 449583730 IUPAC name 8 6 methyl 8 piperidin 1 ylcarbonyl 9,10 didehydroergoline image LSD Pip.svg width 200 Clinical data tradename Identifiers CAS number 50485 23 9 PubChem 308707 DrugBank Ref drugbankcite correct drugbank Chemical data C 21 H 25 N 3 O 1 molecular weight 335.442 g mol smiles c14c2cccc4ncc1CC3C2 CC CN3C C O N5CCCCC5 LSD Pip is a compound from the ergoline family, related to LSD but with the N,N diethyl substitution replaced by a piperidine group. It is more potent than the corresponding pyrrolidine and morpholine analogues LPD 824 and LSM 775 respectively , but is still several times less potent than LSD as a 5 HT2A receptor 5 HT sub 2A sub agonist . ref http proquest.umi.com pqdlink?Ver 1&Exp 01 23 2014&FMT 7&DID 1417800971&RQT 309&attempt 1&cfc 1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007. ref Early studies suggested this compound to be inactive as a hallucinogen in humans, ref name pmid13502837 cite journal author CERLETTI A, DOEPFNER W title Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids journal The Journal of Pharmacology and Experimental Therapeutics volume 122 issue 1 pages 124 36 year 1958 month January pmid 13502837 doi url ref though this does not seem to have been confirmed by any more recent work. See also Lysergic acid 2 butyl amide Lysergic acid 2,4 dimethylazetidide References reflist Serotonergics Ergolines Category Lysergamides Category Serotonin receptor agonists Category Piperidines nervous system drug stub ... more details
Drugbox verifiedrevid 420433443 IUPAC name 4 Fluoro 5 Methoxy N , N dimethyltryptamine image 4 Fluoro 5 methoxy N,N dimethyltryptamine.svg width Clinical data tradename pregnancy category legal status routes of administration Pharmacokinetic data bioavailability protein bound metabolism elimination half life excretion Identifiers CAS number 312314 18 4 ATC prefix ATC suffix PubChem Chemical data C 13 H 17 F 1 N 2 O 1 molecular weight 236,13 g mol smiles 4 Fluoro 5 Methoxy N , N dimethyltryptamine 4 F 5 MeO DMT was first described by David E. Nichols team in 2000. It is a potent 5 HT sub 1A sub agonist. Substitution with the 4 fluorine markedly increased 5 HT sub 1A sub selectivity over 5 HT sub 2A 2C sub receptors with potency greater than that of the 5 HT sub 1A sub agonist 8 OH DPAT . ref cite journal author Joseph B. Blair, Deborah Kurrasch Orbaugh, Danuta Marona Lewicka, Medhane G. Cumbay, Val J. Watts, Eric L. Barker, and David E. Nichols title Effect of Ring Fluorination on the Pharmacology of Hallucinogenic Tryptamines journal Journal of Medicinal Chemistry year 2000 volume 43 issue 24 pmid 11101361 pages 4701 4710 doi 10.1021 jm000339w ref The analog compound with the N , N dialkyl substituents constrained into a pyrrolidine ring, is a slightly stronger agonist for the 5 HT sub 1A sub receptor and retains the selectivity over the 5 HT sub 2A 2C sub receptors. ref cite journal doi 10.1016 S0960 894X 01 00062 2 author Uros Laban, Deborah Kurrasch Orbaugh, Danuta Marona Lewicka and David E. Nichols title A Novel Fluorinated Tryptamine with Highly Potent Serotonin 5 HT1A Receptor Agonist Properties journal Bioorganic & Medicinal Chemistry Letters year 2001 volume 11 issue 6 pages 793 795 pmid 11277522 ref See also 5 F AMT 5 fluoro AMT 6 fluoro DMT References Reflist 2 Hallucinogens Tryptamines DEFAULTSORT Fluoro 5 methoxy DMT, 4 Category Psychedelic tryptamines Category Tryptamines hallucinogen stub ... more details
Wikify date January 2012 Drugbox IUPAC name E 1 2 4 1 4 Iodophenyl 2 phenylbut 1 en 1 yl phenoxy ethyl pyrrolidine image Idoxifene.svg alt Clinical data tradename pregnancy AU A B1 B2 B3 C D X pregnancy US A B C D X pregnancy category legal AU S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled legal CA OTC, Rx only, Schedule I, II, III, IV, V, VI, VII, VIII legal UK GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD Benz POM, CD Anab POM or CD Inv POM legal US OTC Rx only Schedule I, II, III, IV, V legal status routes of administration Pharmacokinetic data bioavailability protein bound metabolism elimination half life excretion Identifiers CAS number 116057 75 1 ATCvet ATC prefix none if uncategorised ATC suffix PubChem DrugBank UNII Ref fdacite correct FDA UNII 456UXE9867 ChEMBL 6318 Chemical data C 28 H 30 I 1 N 1 O 1 molecular weight 523.4 g mol Idoxifene is a non steroidal estrogen antagonist. ref cite journal pmid 2585441 year 1989 last1 McCague first1 R last2 Leclercq first2 G last3 Legros first3 N last4 Goodman first4 J last5 Blackburn first5 GM last6 Jarman first6 M last7 Foster first7 AB title Derivatives of tamoxifen. Dependence of antiestrogenicity on the 4 substituent volume 32 issue 12 pages 2527 33 journal Journal of medicinal chemistry ref It is also structurally analogous to tamoxifen . References Reflist Estrogenics Category Hormonal agents Category Organoiodides Category Pyrrolidines Category Selective estrogen receptor modulators pharma stub ... more details
in Figure 1. Subsequent protonolysis by incoming substrate gives the vinyl pyrrolidine ... thumb center 600px Figure 1. The catalytic hydroamination of aminoallenes to form chiral vinyl pyrrolidine ... more details
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