br Pyrroline one double bond br Pyrrolizidine two pentagonal rings Pyrrolidine , also known as tetrahydropyrrole ... like. ref 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 ... compounds e.g. piracetam , aniracetam . A pyrrolidine ring is the central structure of the amino acid s proline and hydroxyproline . Pyrrolidine is a strong base and is by its basicity one of the strongest simple amines known. In organic chemistry, pyrrolidine is used to activate ketone s and aldehyde ... msds 96268.htm Pyrrolidine MSDS References references Category Pyrrolidines Category Solvents ar de Pyrrolidin fr Pyrrolidine id Pirolidina lv Pirolid ns nl Pyrrolidine ja ... more details
Chembox 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 MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt 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 synthetase . 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 ... 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
Cucurbitin is a protein and a carboxy pyrrolidine that can eliminate parasitic worms. It is found in cucurbita seeds. ref http www.drugs.com npp pumpkin.html ref On February 24, 1992, a patent was filed to use it in cosmetics and pharmaceuticals. ref http www.wipo.int pctdb en wo.jsp?wo 1992015563 ref References reflist External links http www.rcsb.org pdb explore biologyAndChemistry.do?structureId 2EVX Protein Data Bank protein stub ru Category Proteins ... more details
Drugbox IUPAC name 1 2 E 4 4 chlorophenyl 3 phenylbut 2 en 1 yl pyrrolidine image pyrrobutamine.png CAS number 91 82 7 ATC prefix R06 ATC suffix AX08 PubChem 5284614 C 20 H 22 Cl 1 N 1 molecular weight 311.848 g mol bioavailability protein bound metabolism elimination half life excretion pregnancy category legal status routes of administration 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
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 ... more details
Drugbox IUPAC name 2 1 oxo 1 phenylpropan 2 yl isoindole 1,3 dione image Phthalprop.svg width 200 CAS number 19437 20 8 ATC prefix none ATC suffix PubChem 519663 DrugBank C 17 H 13 N 1 O 3 molecular weight 279.29 bioavailability metabolism elimination half life excretion pregnancy category legal status routes of administration 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 Springer D, Fritschi G, Maurer HH. Metabolism of the new designer drug alpha pyrrolidinopropiophenone PPP and the toxicological detection of PPP and 4 methyl alpha pyrrolidinopropiophenone MPPP studied in rat urine using gas chromatography mass spectrometry. Journal of Chromatography B. Analytical Technologies in the Biomedical and Life Sciences . 2003 Nov 5 796 2 253 66. PMID 14581066 ref It is unclear how rapidly or to what extent this metabolic pathway is followed in humans however, and the phthalimido substituted cathinones encountered may have been produced merely as a more sta ... more details
chembox Name PolyDADMAC ImageFile PolyDADMAC.png ImageSize 150px IUPACName SystematicName OtherNames Poly dimethyldiallylammonium chloride Section1 Chembox Identifiers Abbreviations 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 pyrrolidine structure clear left Applications Eff ... 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
The Hofmann L ffler reaction or Hofmann L ffler Freytag Reaction is an organic reaction is which a haloamine is converted to a cyclic amine such as a pyrrolidine with heat and an acid. ref Cite doi 10.1002 cber.188301601120 ref ref Cite doi 10.1002 cber.19090420377 ref ref JerryMarch ref An example is the synthesis of n butylpyrrolidine ref Organic Syntheses , Coll. Vol. 3, p.159 1955 Vol. 25, p.14 1945 . http www.orgsynth.org orgsyn pdfs CV3P0159.pdf ref Image Hofmann Loffler reaction.svg center 800px Hofmann L ffler reaction The reaction type is a radical reaction . In the key step a hydrogen atom migrates from a gamma or delta carbon position to a nitrogen centred radical in a rearrangement reaction . The distal radical is quenched by removing a chlorine atom from a second molecule of the chloroamine, regenerating the nitrogen radical and chain carrying the reaction. A conceptually related reaction is the Barton reaction . References Reflist DEFAULTSORT Hofmann Loffler Reaction Category Substitution reactions Category Name reactions pt Rea o de Hofmann L ffler zh Hofmann L ffler Freytag ... more details
3 Methyl 4 morpholino 2,2 diphenylbutyryl pyrrolidine, and its molecular formula C sub 25 sub H sub ... 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 potent when methylated ... isomer was more active iii while morpholine, dimethylamine, pyrrolidine and piperidine were all active ... activity. So dextromoramide, with a pyrrolidine ring on the 1 amide position, a dextro methyl ... more details
substrate gives the vinyl pyrrolidine 1 or tetrahydropyridine 2 product. There is substantial ... of aminoallenes to form chiral vinyl pyrrolidine 1 and tetrahydropyridine 2 products. L sub 2 ... 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 intramolcular 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 Cope ... 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 fr Cuscohygrine ... more details
chembox Verifiedfields changed verifiedrevid 400113025 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 changed 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 496 49 1 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 ency 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 es Higrina fr Hygrine pt Higrina ru sv Hygrin ... more details
Drugbox verifiedrevid 401043924 IUPAC name 1 1 phenylcyclohexyl pyrrolidine image Rolicyclidine.svg width 125px ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 56218 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 smiles c1ccccc1C3 N2CCCC2 CCCCC3 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 CAS number 2201 39 0 ATC prefix none ATC suffix PubChem 62436 DrugBank C 16 H 23 N 1 molecular weight 229.361 g mol bioavailability metabolism elimination half life excretion pregnancy category legal status Schedule I Class A routes of administration 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 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 ru sv Pyrrolin zh ... more details
drugbox IUPAC name 1 1 methyl 3,3 di 2 thienylprop 2 en 1 yl pyrrolidine image Pyrrolidinylthiambutene.png width 180 CAS number ATC prefix none ATC suffix PubChem 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 bioavailability protein bound metabolism elimination half life excretion pregnancy AU pregnancy US pregnancy category legal AU legal CA legal UK legal US legal status routes of administration 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. PMID 15409854 ref ref Adamson DW, Duffin WM, Green AF. Dithienylbutylamines as analgesics. Nature . 1951 Jan 27 167 4239 153 4. 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 pharm stub Opioids Category Opioids Category Thiophenes Category Pyrrolidines Category Mu opioid agonists ... more details
DISPLAYTITLE 4 Hydroxy N methyl , N trimethylene tryptamine drugbox drug name 4 Hydroxy N methyl , N trimethylene tryptamine IUPAC name R 3 N methylpyrrolidin 2 ylmethyl 4 hydoxyindole image 4 HO N Me TMT.png width 180 CAS number 250672 65 2 ATC prefix ATC suffix PubChem 10466404 C 14 H 17 N 2 O 1 molecular weight 229.297 g mol smiles c3ccc2ncc c2c3O CC1CCCN1C melting point melting high bioavailability protein bound metabolism elimination half life excretion pregnancy AU pregnancy US pregnancy category legal AU legal CA legal UK legal US legal status routes of administration 4 HO MPMI also known as 4 Hydroxy N methyl , N trimethylene tryptamine or lucigenol is a tryptamine derivative that is a hallucinogenic drug. It was developed by the team led by David Nichols from Purdue University in the late 1990s. This compound produces hallucinogen appropriate responding in animal tests with a similar potency to the amphetamine derived hallucinogen 2,5 dimethoxy 4 iodoamphetamine DOI , and has two enantiomer s, with only the R enantiomer being active. ref cite journal doi 10.1021 jm990325u author Gerasimov M, Marona Lewicka D, Kurrasch Orbaugh DM, Qandil AM, Nichols DE title Further studies on oxygenated tryptamines with LSD like activity incorporating a chiral pyrrolidine moiety into the side chain journal Journal of Medicinal Chemistry year 1999 volume 42 issue 20 pages 4257 4263 pmid 10514296 ref The binding affinity for 5 HT2A receptor is 13 2 nM Ki 125I DOI . It is reported at doses starting at 0.5 mg and 1.0 1.5 mg seem to be psychedelic doses. The duration it is reported between six to eight hours. The effects, still not too documented, are OEV CEV, sedation and anxiety. ref http www.hipforums.com newforums showthread.php?t 315326 ref rs date October 2010 See also 4 HO pyr T 5 MeO MPMI 5 MeO pyr T References reflist Hallucinogenic tryptamines DEFAULTSORT Hydroxy N Methyl , N Trimethylene Tryptamine, 4 Category Psychedelic tryptamines ... more details
drugbox verifiedrevid 403510796 IUPAC name 1,2 dimethyl 3 phenylpyrrolidin 3 yl propionate image Prodilidine.png width 240 CAS number 3734 17 6 synonyms ATC prefix none ATC suffix PubChem 19514 DrugBank C 15 H 21 N 1 O 2 molecular weight 247.333 g mol smiles CCC O OC1 CCN C1C C C2 CC CC C2 bioavailability protein bound metabolism elimination half life excretion pregnancy AU A B1 B2 B3 C D X pregnancy US A B C D X pregnancy category legal AU Unscheduled S2 S3 S4 S5 S6 S7 S8 S9 legal CA legal UK legal US legal status routes of administration Prodilidine is an opioid analgesic which is a ring contracted analogue of prodine . It has around the same efficacy as codeine , but is only around 1 3 the potency, and has little abuse potential . ref http www.unodc.org unodc en data and analysis bulletin bulletin 1964 01 01 1 page005.html Fraser HF. Addictiveness of 1,2 dimethyl,3 phenyl,3 propionoxy pyrrolidine hydrochloride ARC I O 1 UNODC Bulletin on Narcotics 1964 Issue 1. ref ref Splitter SR. Treatment of pain in patients with a new nonnarcotic analgesic, prodilidine hydrochloride Cogesic . Current Therapeutic Research, Clinical and Experimental . 1961 Nov 3 472 7. PMID 13915874 ref ref Kissel JW, Albert JR, Boxill GC. The pharmacology of prodilidine hydrochloride, a new analgetic agent. Journal of Pharmacology and Experimental Therapeutics . 1961 Dec 134 332 40. PMID 14456453 ref ref Weikel JH Jr, Labudde JA. Absorption, excretion and fate of prodilidine. Journal of Pharmacology and Experimental Therapeutics . 1962 Dec 138 392 8. PMID 13999550 ref ref Batterman RC, Mouratoff GJ, Kaufman JE. Prodilidine Hydrochloride A new moderately potent analgesic. American Journal of the Medical Sciences . 1964 Jan 247 62 8. PMID 14106881 ref References references opioids Category Opioids Category Propionates Category Pyrrolidines Category Mu opioid agonists pharm stub ... more details
drugbox image Nafoxidine.png ATC prefix none IUPAC name 1 2 4 6 methoxy 2 phenyl 3,4 dihydronaphthalen 1 yl phenoxy ethyl pyrrolidine C 28 H 31 N 1 O 2 molecular weight 425.562 g mol CAS number 1845 11 0 PubChem 4416 ChEMBL 28211 ChemSpiderID 4263 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 Antineoplastic drugs Category Pyrrolidines Category Phenol ethers Category Dilines Chemotherapeutic agents Sex hormones antineoplastic drug stub ... more details
drugbox verifiedrevid 405763311 IUPAC name 3S 3 2,3 dihydro 5 methoxy 1H inden 4 yl oxy pyrrolidine image Org37684 structure.png width 240 CAS number ATC prefix ATC suffix PubChem 9794656 IUPHAR ligand 171 C 14 H 19 N 1 O 2 molecular weight 233.305 g mol smiles COc1ccc2CCCc2c1OC3CNCC3 bioavailability protein bound metabolism elimination half life excretion pregnancy category legal status Uncontrolled routes of administration 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 IUPAC name 8 6 methyl 8 piperidin 1 ylcarbonyl 9,10 didehydroergoline image LSD Pip structure.png width 200 CAS number 50485 23 9 ATC prefix ATC suffix PubChem 308707 DrugBank C 21 H 25 N 3 O 1 molecular weight 335.442 g mol smiles c14c2cccc4ncc1CC3C2 CC CN3C C O N5CCCCC5 bioavailability metabolism elimination half life excretion pregnancy category legal status routes of administration 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. pharm stub See also Lysergic acid 2 butyl amide Lysergic acid 2,4 dimethylazetidide References reflist Serotonergics Ergolines Category Lysergamides Category Serotonin receptor agonists Category Piperidines ... more details
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