3-(Pyrrolidin-2-yl)pyridine (HCID 412)

Names & identifiers

Preferred name: 3-(Pyrrolidin-2-yl)pyridine
IUPAC: 3-pyrrolidin-2-ylpyridine
English name: 3-(2-Pyrrolidinyl)pyridine
Molecular formula: C9H12N2
Molecular weight: 148.21

Names & synonyms

3-(pyrrolidin-2-yl)pyridineRefChem:496138637-353-05746-86-13-pyrrolidin-2-yl-pyridine(+-)-NornicotineDL-NORNICOTINE(+/-)-NornicotineMFCD00016913(+-)-1'-Demethylnicotinedl-Norcitine( inverted exclamation markA)-Nornicotine

Show more names

Nornicotine(R,S)-NORNICOTINE3-PYRROLIDIN-2-YLPYRIDINE(±)-NornicotineNORNICOTINE, DL-Nicotine USP RC FDL-Nornicotine,96%beta-dl-nornicotine

3-(2-Pyrrolidyl)pyridine(+-)-3-(2-Pyrrolidinyl)pyridine(S)-3-Pyrrolidin-2-yl-pyridine2-(3-PYRIDINYL)PYRROLIDINE13450-58-3(S)-2-(3-Pyridyl)pyrrolidineSMR000449277(R,S)-Nornicotine (1.0 mg/mL in Methanol)

Database identifiers

CAS: 494-97-3、5746-86-1
PubChem CID: 412
DTXSID: DTXSID50862034
EC Number: 637-353-0
Nikkaji: J391.269H

Properties

Computed structural properties

XLogP: 0.2
Topological polar surface area: 24.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 11
Formal charge: 0
Complexity: 125

Experimental & physicochemical properties

LogP0.17

Boiling Point270 °C

Physical DescriptionLiquid

Kovats Retention Index1435.4

Physicochemical properties

Melting point: 235 · 235-236 °C(Solv: ethanol (64-17-5))
Boiling point: 107 · 107-108°C 2mm
Density: 1 · 1,074 g/cm3
refractive index: 1.54 · 1.54
Flash point: 101 °C · 101°C
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: 50 mg/mL
form: liquid
pka: 9.09 · 9.09±0.10(Predicted)
color: yellow
Specific Gravity: 1.074 · 1.074
Water Solubility: Soluble in acetone, chloroform and water (50mg/ml).
Merck: 14 · 14,6712
BRN: 81968 · 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 · 5746-86-1(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 83 H6L5QD8Z · 83H6L5QD8Z
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn,Xi,T,F
Risk Statements: 20 · 20/21/22-36/37/38-39/23/24/25-23/24/25-11
Safety Statements: 26 · 26-36/37-45-16-7
RIDADR: 2810 · 2810
WGK Germany: 3 · 3
RTECS: 6350000 · QS6350000
F: 3 · 3-10
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29399990 · 29399990
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Toxicity: 6 mg/kg · LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (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 exposure; Respiratory 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 information

Hazard Classes and CategoriesAcute Tox. 4 (98%)；Acute Tox. 4 (98%)；Skin Irrit. 2 (98%)；Eye Irrit. 2 (100%)；Acute Tox. 4 (98%)；STOT SE 3 (87.8%)

Safety data

F: 3-10
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
rtecs: QS6350000
ridadr: 2810
hs_code: 29399990
Toxicity: LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47
risk_code: 20/21/22-36/37/38-39/23/24/25-23/24/25-11
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn,Xi,T,F
safety_code: 26-36/37-45-16-7
hazard_class: 6.1
Storage Class: 10 - Combustible liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H302+H312+H332-H315-H319-H335
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/MetabolitesNornicotine is a known thirdhand smoke metabolite of Nicotine.

Tissue LocationsKidney；Liver

Cellular LocationsCytoplasm

Metabolite PathwaysNicotine Action Pathway；Nicotine Metabolism Pathway

Uses & manufacturing

Use ClassificationNatural products -> Stimulants -> Transformation products

Applications · 4 items

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.

UsesA metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions.

UsesA metabolite of Nicotine. Can catalyze aqueous aldol reactions

Uses3-(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).