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C9392

Sigma-Aldrich

(±)-Coniine

≥98%, liquid

Synonym(s):

2-Propylpiperidine

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About This Item

Empirical Formula (Hill Notation):
C8H17N
CAS Number:
3238-60-6
Molecular Weight:
127.23
EC Number:
221-801-3
MDL number:
MFCD00056022
UNSPSC Code:
12352200
PubChem Substance ID:
24893155

assay

≥98%

form

liquid

color

, clear colorless to yellow-green

density

0.85 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCCC1CCCCN1

InChI

1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3

InChI key

NDNUANOUGZGEPO-UHFFFAOYSA-N

Application

Coniine, a neurotoxic alkaloid from hemlock, is used in comparative analysis versus other alkaloids that act at the level of the nicotinic acid/nicotinic acetylcholine (nAChR) receptors.

Other Notes

Toxic principle of poison hemlock (racemic modification).

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Carc. 2 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

119.3 °F - closed cup

flash_point_c

48.5 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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D Rizzi et al.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 6(12), 939-943 (1991-01-11)
In the past, hemlock poisoning was only known for its neurotoxic effects; quite recently non-neurological features, consisting of rhabdomyolysis and acute renal failure, have been also described. Here we report our experience with these clinical findings, which we frequently observe
T J Wilkinson et al.
Organic letters, 2(2), 155-158 (2000-05-18)
[reaction: see text] Sequences of lithiation-substitution, enantioselective hydrogenation, and diastereoselective lithiation-substitution provide efficient highly enantioselective syntheses of 2-substituted and cis and trans 2,6-disubstituted piperidines. The methodology is demonstrated by syntheses of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine as their hydrochlorides.
Nutrition borne myolysis; an uncommon cause of myolysis in Europe.
R Tzanetea et al.
Upsala journal of medical sciences, 105(3), 255-257 (2001-03-23)
J F Hayes et al.
Chemical communications (Cambridge, England), (18)(18), 1784-1785 (2002-09-21)
(S)-Coniine is made using a reaction which assembles the piperidine ring by the sequential formation of four new chemical bonds and installs the C-2 stereogenic centre with high levels of diastereocontrol (90% de).
F D Galey et al.
Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc, 4(1), 60-64 (1992-01-01)
Cattle in two herds developed signs of bloating, increased salivation and lacrimation, depression, respiratory distress, ataxia, and death after ingestion of hay that contained large amounts of poison hemlock (Conium maculatum). Twenty of 30 Angus cows and calves were affected
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