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134759

Sigma-Aldrich

1,2,3,6-Tetrahydropyridine

97%

Synonym(s):

Δ3-Piperidine, 1,2,5,6-Tetrahydropyridine, 3,6-Dihydro-2H-pyridine

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About This Item

Empirical Formula (Hill Notation):
C5H9N
CAS Number:
694-05-3
Molecular Weight:
83.13
EC Number:
211-766-2
MDL number:
MFCD00005949
UNSPSC Code:
12352100
PubChem Substance ID:
24848181
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.48 (lit.)

bp

108 °C (lit.)

mp

−48 °C (lit.)

density

0.911 g/mL at 25 °C (lit.)

SMILES string

C1CC=CCN1

InChI

1S/C5H9N/c1-2-4-6-5-3-1/h1-2,6H,3-5H2

InChI key

FTAHXMZRJCZXDL-UHFFFAOYSA-N

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Application

Used to form ene-endo-spirocyclic ammonium ylids for [2,3]-sigmatropic rearrangement to pyrroloazepinones and oxazepinones.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °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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Shin'Ichiro Satake et al.
The European journal of neuroscience, 52(3), 3002-3021 (2020-05-10)
Synaptic vesicle exocytosis is triggered by Ca2+ influx through several subtypes of voltage-gated calcium channels in the presynaptic terminal. We previously reported that paired-pulse stimulation at brief intervals increases Cav 2.1 (P/Q-type) channel-mediated multivesicular release (MVR) at glutamatergic synapses between
Edward Roberts et al.
Organic letters, 7(10), 2075-2078 (2005-05-07)
The first examples of sigmatropic rearrangements of ene-endo-spirocyclic, tetrahydropyridine-derived ammonium ylids are reported. Thus, spiro[6.7]-ylids rearrange primarily by a [2,3]-pathway, whereas the analogous [6.6]-ylids rearrange by [1,2]- and [2,3]-mechanisms in roughly equal proportions. This method serves as a rapid entry
Santhosh Sethuramanujam et al.
Journal of neurophysiology, 112(1), 193-203 (2014-04-11)
Glutamate release at bipolar to ganglion cell synapses activates NMDA and AMPA/kainic acid (KA) ionotropic glutamate receptors. Their relative strength determines the output signals of the retina. We found that this balance is tightly regulated by presynaptic inhibition that preferentially
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Molecular vision, 23, 334-345 (2017-07-01)
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L-3,4-dihydroxyphenylalanine (L-DOPA) is the most effective anti-parkinsonian agent available, but upon chronic administration, patients with Parkinson's disease (PD) experience abnormal involuntary movements, dyskinesia. Modulation of serotonin 1A (5-HT1A) receptors is regarded as an effective way to alleviate dyskinesia, yet this
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