C9392
(±)-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:
Recommended Products
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 Statements
Precautionary Statements
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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Benedict T Green et al.
Neurotoxicology and teratology, 32(3), 383-390 (2010-02-02)
Teratogenic alkaloids are found in many species of plants including Conium maculatum L., Nicotiana glauca, Nicotiana tabaccum, and multiple Lupinus spp. Fetal musculoskeletal defects produced by alkaloids from these plants include arthrogyropisis, scoliosis, torticollis, kyposis, lordosis, and cleft palate. A
Anthony J Burke et al.
Organic & biomolecular chemistry, 2(9), 1387-1394 (2004-04-24)
Conjugate addition of lithium (S)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha, beta-unsaturated Weinreb amides proceeds with high levels of diastereoselectivity (>95% de). The beta-amino Weinreb amide products may be transformed into beta-amino ketones via reactions with Grignard reagents, while treatment with
Ingestion of poison hemlock (Conium maculatum).
B S Frank et al.
The Western journal of medicine, 163(6), 573-574 (1995-12-01)
T Blitzke et al.
Phytochemistry, 55(8), 979-982 (2001-01-05)
Phytochemical investigations of Aloe sabaea afforded a new chlorinated amide, N-4'-chlorobutylbutyramide, and the toxic piperidine alkaloids coniine, gamma-coniceine and the quarternary N,N-dimethylconiine. This is the first report of the occurrence of a chlorinated compound in the Aloeaceae family.
Versatile one-pot reductive alkylation of lactams/amides via amide activation: application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine.
Kai-Jiong Xiao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(43), 12792-12796 (2010-10-13)
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