3-(Pyrrolidin-2-yl)pyridine
Nornicotine · DL-NORNICOTINE · (R,S)-NORNICOTINE · 3-PYRROLIDIN-2-YLPYRIDINE · (±)-Nornicotine · NORNICOTINE, DL- · Nicotine USP RC F · (+/-)-nornicotine
Identifikatoren & physikalische Daten
| CAS No. | 494-97-3 |
|---|---|
| Summenformel | C9H12N2 |
| Durchschnittliche Molmasse | 148,2 g/mol |
| Monoisotopische Masse | 148,10004839 g/mol |
| SMILES | c1cncc(C2CCCN2)c1 |
| InChIKey | MYKUKUCHPMASKF-UHFFFAOYSA-N |
| PubChem CID | 412 |
| EC No. | 637-353-0 |
| DTXSID | DTXSID50862034 |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 24,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 125 |
| LogP (Verteilungskoeffizient) | 0.17 |
| Siedepunkt | 270 °C107-108°C 2mm |
| Physical Description | Liquid |
| Kovats Retention Index | 1435.4 |
| Schmelzpunkt | 235-236 °C(Solv: ethanol (64-17-5)) |
| Dichte | 1,074 g/cm3 |
| Brechungsindex | 1.54 |
| Flammpunkt | 101°C |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | H2O: 50 mg/mLSoluble in acetone, chloroform and water (50mg/ml). |
| Aggregatzustand | liquid |
| pKa (Säurekonstante) | 9.09±0.10(Predicted) |
| Farbe | yellow |
| Wichte | 1.074 |
| Merck | 14,6712 |
| BRN | 81968 |
| Stabilität | 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 Datenbank | 5746-86-1(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (98%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (98%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (98%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (87.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 49 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (98%)Skin Irrit. 2 (98%)Eye Irrit. 2 (100%)STOT SE 3 (87.8%) |
| F | 3-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 2810 |
| Zollcode | 29399990 |
| RTECS-Nr. | QS6350000 |
| R-Sätze (R) | 20/21/22-36/37/38-39/23/24/25-23/24/25-11 |
| Toxizität | LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47 |
| Gefahrensymbole | Xn,Xi,T,F |
| Sicherheitshinweise (S) | 26-36/37-45-16-7 |
| Gefahrenklasse | 6.1Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Beschreibung
(±)-Nornicotine is a metabolite of nicotine 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. Nornicotine promotes cell migration and destabilizes cell-cell junctions in an endothelial cell line. It is generally thought to be free from abuse potential, but it has been self-administered by rats. It can be detected in urine.
Verwenden
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).