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679097

Sigma-Aldrich

(R)-(−)-2-Methylpyrrolidine

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About This Item

Empirical Formula (Hill Notation):
C5H11N
CAS Number:
41720-98-3
Molecular Weight:
85.15
MDL number:
MFCD07783026
UNSPSC Code:
12352005
PubChem Substance ID:
24885467
NACRES:
NA.22

refractive index

n20/D 1.4353

density

0.842 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H]1CCCN1

InChI

1S/C5H11N/c1-5-3-2-4-6-5/h5-6H,2-4H2,1H3/t5-/m1/s1

InChI key

RGHPCLZJAFCTIK-RXMQYKEDSA-N

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Application

(R)-(−)-2-Methylpyrrolidine, an optically active amine that can be used as a key building block to synthesize:
  • 4,5-fused pyridazinone derivatives are applicable as potent histamine H3 receptor antagonists.
  • Naphthalenoid histamine H3 receptor antagonist.
  • Pyrrolo[2,3-d]pyrimidine derivatives as potent inhibitors of leucine-rich repeat kinase 2.

Signal Word

Danger

Hazard Statements

H225,H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

45.0 °F - closed cup

Flash Point(C)

7.22 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro SAR of pyrrolidine-containing histamine H 3 receptor antagonists: Trends across multiple chemical series
Nersesian, Diana L., et al.
Bioorganic & Medicinal Chemistry Letters, 18.1, 355-359 (2008)
An expedient and multikilogram synthesis of a naphthalenoid H3 antagonist.
Pu YM, et al.
Organic Process Research & Development, 11(6), 1004-1009 (2007)
Optical Activation of Racemic a-Substituted Carbonyl Compounds Using Optically Active Amines.
Matsushita H, et al.
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Ming Tao et al.
Bioorganic & medicinal chemistry letters, 21(20), 6126-6130 (2011-09-13)
Three series of novel 4,5-fused pyridazinones were synthesized as histamine H(3) receptor antagonists. The 2,5,6,7-tetrahydrocyclopenta[d]pyridazin-1-one 5q and 5,6,7,8-tetrahydro-2H-phthalazin-1-one 5u displayed high affinity at both rat and human H(3) receptors, and showed potent antagonist and full inverse agonist activity in functional
Douglas S Williamson et al.
Journal of medicinal chemistry, 64(14), 10312-10332 (2021-06-30)
Inhibitors of leucine-rich repeat kinase 2 (LRRK2) and mutants, such as G2019S, have potential utility in Parkinson's disease treatment. Fragment hit-derived pyrrolo[2,3-d]pyrimidines underwent optimization using X-ray structures of LRRK2 kinase domain surrogates, based on checkpoint kinase 1 (CHK1) and a
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