3-(Pyrrolidin-2-yl)pyridine
Nornicotine · DL-NORNICOTINE · (R,S)-NORNICOTINE · 3-PYRROLIDIN-2-YLPYRIDINE · (±)-Nornicotine · NORNICOTINE, DL- · Nicotine USP RC F · (+/-)-nornicotine
Identifiers & Physical Properties
| CAS No. | 494-97-3 |
|---|---|
| Molecular formula | C9H12N2 |
| Average molar mass | 148.2 g/mol |
| Monoisotopic mass | 148.10004839 g/mol |
| SMILES | c1cncc(C2CCCN2)c1 |
| InChIKey | MYKUKUCHPMASKF-UHFFFAOYSA-N |
| PubChem CID | 412 |
| EC No. | 637-353-0 |
| DTXSID | DTXSID50862034 |
Chemical & Physical Properties
| XLogP | 0.2 |
|---|---|
| Topological polar surface area | 24.9 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 125 |
| LogP (partition coefficient) | 0.17 |
| Boiling point | 270 °C107-108°C 2mm |
| Physical Description | Liquid |
| Kovats Retention Index | 1435.4 |
| Melting point | 235-236 °C(Solv: ethanol (64-17-5)) |
| Density | 1,074 g/cm3 |
| Refractive index | 1.54 |
| Flash point | 101°C |
| Storage conditions | 2-8°C |
| Solubility | H2O: 50 mg/mLSoluble in acetone, chloroform and water (50mg/ml). |
| Physical state | liquid |
| pKa (acidity coefficient) | 9.09±0.10(Predicted) |
| Color | yellow |
| Specific gravity | 1.074 |
| 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) |
| EWG's Food Scores | 1 |
| FDA UNII | 83H6L5QD8Z |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302+H312+H332-H315-H319-H335 |
| GHS precautionary statements | P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,Xi,T,F |
| Risk statements (R) | 20/21/22-36/37/38-39/23/24/25-23/24/25-11 |
| Safety statements (S) | 26-36/37-45-16-7 |
| UN transport number | 2810 |
| Water hazard class (WGK) | 3 |
| RTECS number | QS6350000 |
| F | 3-10 |
| Hazard class | 6.1Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Packing group | III |
| Customs code | 29399990 |
| Storage class | 10 - Combustible liquids |
| Toxicity | LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47 |
Safety & Regulations
| GHS classification | 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 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| RTECS number | QS6350000 |
| UN transport number | 2810 |
| Customs code | 29399990 |
| Toxicity | LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47 |
| Risk statements (R) | 20/21/22-36/37/38-39/23/24/25-23/24/25-11 |
| Signal word |
Applications & Uses
Description
(±)-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.
Uses
A metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions.
Uses
A metabolite of Nicotine. Can catalyze aqueous aldol reactions
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).