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Pyrrolidine information


Pyrrolidine
Names
Preferred IUPAC name
Pyrrolidine[1]
Other names
Azolidine
Azacyclopentane
Tetrahydropyrrole
Prolamine
Azolane
Identifiers
CAS Number
  • 123-75-1 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
102395
ChEBI
  • CHEBI:33135 checkY
ChEMBL
  • ChEMBL22830 checkY
ChemSpider
  • 29008 checkY
ECHA InfoCard 100.004.227 Edit this at Wikidata
EC Number
  • 204-648-7
Gmelin Reference
1704
PubChem CID
  • 31268
RTECS number
  • UX9650000
UNII
  • LJU5627FYV checkY
UN number 1922
CompTox Dashboard (EPA)
  • DTXSID3059559 Edit this at Wikidata
InChI
  • InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 checkY
    Key: RWRDLPDLKQPQOW-UHFFFAOYSA-N checkY
  • InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
    Key: RWRDLPDLKQPQOW-UHFFFAOYAX
SMILES
  • C1CCNC1
Properties
Chemical formula
C4H9N
Molar mass 71.123 g·mol−1
Appearance Clear colorless liquid
Density 0.866 g/cm3
Melting point −63 °C (−81 °F; 210 K)
Boiling point 87 °C (189 °F; 360 K)
Solubility in water
Miscible
Acidity (pKa) 11.27 (pKa of conjugate acid in water),[2]

19.56 (pKa of conjugate acid in acetonitrile)[3]

Magnetic susceptibility (χ)
-54.8·10−6 cm3/mol
Refractive index (nD)
1.4402 at 28°C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
highly flammable, harmful, corrosive, possible mutagen
GHS labelling:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H225, H302, H314, H332
Precautionary statements
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
3
1
Flash point 3 °C (37 °F; 276 K)
Autoignition
temperature
345 °C (653 °F; 618 K)
Safety data sheet (SDS) MSDS
Related compounds
Related nitrogen heterocyclic compounds
Pyrrole (aromatic with two double bonds)
Pyrroline (one double bond)
Pyrrolizidine (two pentagonal rings)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic odor that has been described as "ammoniacal, fishy, shellfish-like".[4] In addition to pyrrolidine itself, many substituted pyrrolidines are known.

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  3. ^ Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". The Journal of Organic Chemistry. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.
  4. ^ Pyrrolidine Archived 2017-11-21 at the Wayback Machine, The Good Scents Company

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Pyrrolidine

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Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified...

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Pyrrolidine dithiocarbamate

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Pyrrolidine dithiocarbamate (PDTC) are a family of closely related drugs used for a metal chelation, induction of G1 phase cell cycle arrest, and preventing...

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Pyrrolidine alkaloids

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The pyrrolidine alkaloids are natural products chemically derived from pyrrolidine. Alkaloids with partial pyrrolidine structure are usually sub-categorized...

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Coca alkaloid

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coca plant, Erythroxylum coca. They are predominantly of either the pyrrolidine or the tropane types. Benzoylecgonine Cocaine Ecgonidine Ecgonine Hydroxytropacocaine...

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Dextromoramide

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features; (i) at the 1-amide group only the pyrrolidine and dimethylamide substituents were active, with pyrrolidine being more potent (ii) the alkyl chain...

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Kainic acid

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then catalyzes the stereocontrolled formation of the trisubstituted pyrrolidine ring, taking prekainic acid to the final kainic acid. KabC was also able...

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Methylenedioxypyrovalerone

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likely to consist of either pyrrolidine or alpha-dibrominated alkylphenones—respectively, from either excess pyrrolidine or incomplete amination during...

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PolyDADMAC

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DADMAC: N-substituted piperidine structure or N-substituted pyrrolidine structure. The pyrrolidine structure is favored. PolyDADMAC is used in waste water...

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Pyroglutamic acid

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Pyroglutamic acid (also known as PCA, 5-oxoproline, pidolic acid) is a ubiquitous but understudied natural amino acid derivative in which the free amino...

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NNK

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carcinogenesis. The conversion of nicotine to NNK entails opening of the pyrrolidine ring. NNK can be produced by standard methods of organic synthesis. NNK...

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Protonitazepyne

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to propoxy, and the N,N-diethyl substitution has been cyclised into a pyrrolidine ring. While formal studies into its pharmacology have yet to be carried...

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Cocaine

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Claisen condensation. This produces a racemic mixture of the 2-substituted pyrrolidine, with the retention of the thioester from the Claisen condensation. In...

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Phenylethylpyrrolidine

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1-(2-Phenylethyl)pyrrolidine (PEP) is a chemical compound. It is an analogue of 2-phenylethylamine where the amine has been replaced by a pyrrolidine ring. It...

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Alkaloid

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example, nicotine contains a pyridine fragment from nicotinamide and a pyrrolidine part from ornithine and therefore can be assigned to both classes. Alkaloids...

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Anticonvulsant

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Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents...

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MDMA

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Proline

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The "side chain" from the α carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid. It is non-essential in...

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Ketamine

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Fluorolintane

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"Preparation and characterization of the 'research chemical' diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers" (PDF). Drug Testing and...

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Adderall

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Methamphetamine

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Tropane alkaloid

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presence of the bicyclic tropane core. O’Hagan, David (2000). "Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids (1998 to 1999)". Natural...

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Sertraline

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Trazodone

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Diphenhydramine

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Pyrrocaine

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rate compared to lidocaine. Selfsame as lidocaine, albeit interposing pyrrolidine for diethylamine. Amide formation between 2,6-Dimethylaniline (1) and...

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Piracetam

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only. Piracetam is in the racetams group, with chemical name 2-oxo-1-pyrrolidine acetamide. It is a cyclic derivative of the neurotransmitter GABA and...

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Heterocyclic compound

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Tirzepatide

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