| Identification | More | [Name]
3-(2-Pyrrolidinyl)pyridine | [CAS]
5746-86-1 | [Synonyms]
2-[3-PYRIDYL]PYRROLIDINE
2-[3-PYRIDYL]PYRROLIDONE
(+/-)-3-(2-PYRROLIDINYL)PYRIDINE
3-(2-PYRROLIDINYL)PYRIDINE
3-PYRROLIDIN-2-YLPYRIDINE
DL-NORNICOTINE
(+/-)-NORNICOTINE
NORNICOTINE, DL-
(R,S)-NORNICOTINE
(+-)-1’-demethylnicotine
beta-dl-nornicotine
DL-2-(3-Pyridyl)pyrrolidine
(+-)-NORNICOTINE 98+%
DL-Nornicotine,96%
2-(3-Pyridyl)pyrrolidine, 3-(2-Pyrrolidinyl)pyridine | [EINECS(EC#)]
637-353-0 | [Molecular Formula]
C9H12N2 | [MDL Number]
MFCD00016913 | [Molecular Weight]
148.2 | [MOL File]
5746-86-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Colourless Oil | [Melting point ]
235-236 °C(Solv: ethanol (64-17-5)) | [Boiling point ]
107-108°C 2mm | [density ]
1,074 g/cm3 | [refractive index ]
1.54 | [Fp ]
101°C | [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL
| [form ]
liquid
| [pka]
9.09±0.10(Predicted) | [color ]
yellow
| [Specific Gravity]
1.074 | [Water Solubility ]
Soluble in acetone, chloroform and water (50mg/ml). | [Usage]
A metabolite of Nicotine. Can catalyze aqueous aldol reactions | [Merck ]
14,6712 | [BRN ]
81968 | [Stability:]
Hygroscopic, Light Sensitive, Moisture Sensitive | [InChI]
1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2 | [InChIKey]
MYKUKUCHPMASKF-UHFFFAOYSA-N | [SMILES]
C1CNC(C1)c2cccnc2 | [CAS DataBase Reference]
5746-86-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
2810 | [WGK Germany ]
3
| [RTECS ]
QS6350000
| [F ]
3-10 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29399990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Toxicity]
LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47 |
| Hazard Information | Back Directory | [Description]
(±)-Nornicotine is a metabolite of nicotine (Item No. 16535) that acts as a neuronal nicotinic acetylcholine receptor (nAChR) agonist. The α6 and α7 subunit-containing neuronal nAChRs are particularly responsive to nornicotine with EC50 values of approximately 4 and 17 μM, respectively, when expressed in Xenopus oocytes.1 Nornicotine promotes cell migration and destabilizes cell-cell junctions in an endothelial cell line.2 It is generally thought to be free from abuse potential, but it has been self-administered by rats.3,4 It can be detected in urine.5 | [Chemical Properties]
Colourless Oil | [Uses]
3-(2-Pyrrolidinyl)pyridine is a tobacco alkaloid and the major Nicotine (N412420) metabolite in brain. Nornicotine appears to activate different nAChR subtypes, has a better pharmacokinetic profile, and produces less toxicity than Nicotine. Nornicotine shows a significant analgesic activity. Nicotine USP Related Compound F (3-(pyrrolidine-2-yl)pyridine).
| [Uses]
A metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions. | [Uses]
A metabolite of Nicotine. Can catalyze aqueous aldol reactions | [Synthesis Reference(s)]
Tetrahedron Letters, 37, p. 1137, 1996 DOI: 10.1016/0040-4039(96)00002-0 | [Safety Profile]
Poison by intraperitoneal route.When heated to decomposition it emits very toxic fumesof NOx and HCl. See also NORNICOTINE | [References]
[1] ROGER L. PAPKE Peter A C Linda P Dwoskin. The pharmacological activity of nicotine and nornicotine on nAChRs subtypes: relevance to nicotine dependence and drug discovery[J]. Journal of Neurochemistry, 2007, 101 1: 160-167. DOI: 10.1111/j.1471-4159.2006.04355.x
[2] MACIEJ GAGAT. Nornicotine impairs endothelial cell-cell adherens junction complexes in EA.hy926 cell line via structural reorganization of F-actin.[J]. Folia histochemica et cytobiologica, 2013, 51 3: 179-192. DOI: 10.5603/fhc.2013.0026
[3] M T BARDO. Nornicotine is self-administered intravenously by rats.[J]. Psychopharmacology, 1999, 146 3: 290-296. DOI: 10.1007/s002130051119
[4] ALLISON C HOFFMAN Sarah E E. Abuse potential of non-nicotine tobacco smoke components: acetaldehyde, nornicotine, cotinine, and anabasine.[J]. Nicotine & Tobacco Research, 2013, 15 3: 622-632. DOI: 10.1093/ntr/nts192 |
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