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Key Documents

C9392

Sigma-Aldrich

(±)-Coniine

≥98%, liquid

Synonym(s):

2-Propylpiperidine

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About This Item

Empirical Formula (Hill Notation):
C8H17N
CAS Number:
Molecular Weight:
127.23
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

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).

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

119.3 °F - closed cup

Flash Point(C)

48.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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).
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)
C S Forsyth et al.
Teratology, 48(1), 59-64 (1993-07-01)
Conium maculatum (poison hemlock, CM) is teratogenic in several domestic species, presumably due to its piperidine alkaloids, including coniine, which has been verified to be teratogenic in cattle. Coniine/CM teratogenicity culminates in production of arthrogryposis. The purpose of this study

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