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3-(2-Pyrrolidinyl)pyridine, also known as (±)-Nornicotine, is a metabolite of nicotine that acts as a neuronal nicotinic acetylcholine receptor (nAChR) agonist. It is a colorless oil and is the major nicotine metabolite in the brain. Nornicotine is known to activate different nAChR subtypes, has a better pharmacokinetic profile, and produces less toxicity than nicotine. It is generally thought to be free from abuse potential but has been self-administered by rats. It can be detected in urine.

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  • 5746-86-1 Structure
  • Basic information

    1. Product Name: 3-(2-Pyrrolidinyl)pyridine
    2. Synonyms: NORNICOTINE, DL-;(+/-)-NORNICOTINE;(R,S)-NORNICOTINE;(+-)-1’-demethylnicotine;beta-dl-nornicotine;2-[3-PYRIDYL]PYRROLIDINE;2-[3-PYRIDYL]PYRROLIDONE;(+/-)-3-(2-PYRROLIDINYL)PYRIDINE
    3. CAS NO:5746-86-1
    4. Molecular Formula: C9H12N2
    5. Molecular Weight: 148.2
    6. EINECS: 200-659-6
    7. Product Categories: Alkaloids;pharmacetical;Nicotine Derivatives;Benzenes;Metabolites & Impurities;Aromatics;Chiral Reagents;Heterocycles;Mutagenesis Research Chemicals;Heterocycle-Pyridine series
    8. Mol File: 5746-86-1.mol
  • Chemical Properties

    1. Melting Point: 235-236 °C(Solv: ethanol (64-17-5))
    2. Boiling Point: 107-108°C 2mm
    3. Flash Point: 101°C
    4. Appearance: yellow/liquid
    5. Density: 1,074 g/cm3
    6. Vapor Pressure: 0.00702mmHg at 25°C
    7. Refractive Index: 1.54
    8. Storage Temp.: 2-8°C
    9. Solubility: H2O: 50 mg/mL
    10. PKA: 9.09±0.10(Predicted)
    11. Water Solubility: Soluble in acetone, chloroform and water (50mg/ml).
    12. Stability: Hygroscopic, Light Sensitive, Moisture Sensitive
    13. Merck: 14,6712
    14. BRN: 81968
    15. CAS DataBase Reference: 3-(2-Pyrrolidinyl)pyridine(CAS DataBase Reference)
    16. NIST Chemistry Reference: 3-(2-Pyrrolidinyl)pyridine(5746-86-1)
    17. EPA Substance Registry System: 3-(2-Pyrrolidinyl)pyridine(5746-86-1)
  • Safety Data

    1. Hazard Codes: Xn,Xi,T,F
    2. Statements: 20/21/22-36/37/38-39/23/24/25-23/24/25-11
    3. Safety Statements: 26-36/37-45-16-7
    4. RIDADR: 2810
    5. WGK Germany: 3
    6. RTECS: QS6350000
    7. F: 3-10
    8. HazardClass: 6.1
    9. PackingGroup: III
    10. Hazardous Substances Data: 5746-86-1(Hazardous Substances Data)

5746-86-1 Usage

Uses

Used in Pharmaceutical Applications:
3-(2-Pyrrolidinyl)pyridine is used as a pharmaceutical agent for its significant analgesic activity. It activates specific nAChR subtypes, particularly the α6 and α7 subunit-containing neuronal nAChRs, which can be beneficial in the development of new pain management therapies.
Used in Chemical Synthesis:
3-(2-Pyrrolidinyl)pyridine is used as a catalyst for aqueous aldol reactions, which are important in the synthesis of various organic compounds.
Used in Research and Development:
As a metabolite of nicotine, 3-(2-Pyrrolidinyl)pyridine is used in research to study the effects of nicotine and its derivatives on the nervous system and to develop new drugs with improved pharmacological properties and reduced toxicity.
Used in Toxicology and Drug Testing:
3-(2-Pyrrolidinyl)pyridine can be detected in urine, making it a useful biomarker for toxicology and drug testing applications, particularly in monitoring nicotine and its metabolites in individuals.

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

Check Digit Verification of cas no

The CAS Registry Mumber 5746-86-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,4 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5746-86:
(6*5)+(5*7)+(4*4)+(3*6)+(2*8)+(1*6)=121
121 % 10 = 1
So 5746-86-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/p+1/t9-/m0/s1

5746-86-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Alfa Aesar

  • (L10809)  DL-Nornicotine, 98%   

  • 5746-86-1

  • 10mg

  • 489.0CNY

  • Detail
  • Alfa Aesar

  • (L10809)  DL-Nornicotine, 98%   

  • 5746-86-1

  • 50mg

  • 1696.0CNY

  • Detail
  • USP

  • (1463371)  Nicotine Related Compound F  United States Pharmacopeia (USP) Reference Standard

  • 5746-86-1

  • 1463371-20MG

  • 14,500.98CNY

  • Detail

5746-86-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(2-Pyrrolidinyl)pyridine

1.2 Other means of identification

Product number -
Other names 3-pyrrolidin-2-yl-pyridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5746-86-1 SDS

5746-86-1Relevant articles and documents

Preparation method of nicotine and intermediate thereof

-

, (2021/06/02)

The invention relates to a preparation method of nicotine and an intermediate thereof, wherein the intermediate has a structure as shown in a formula (II), X1, X2 and X3 are respectively and independently CR2R3, R1 is a C1-6 alkyl group, and R2 and R3 are each independently H or a C1-6 alkyl group. According to the invention, the preparation method of the nicotine and the intermediate thereof has the advantages of simple operation, mild reaction conditions, easily available raw materials, and high conversion rate, can effectively reduce the production cost of the nicotine, and has the potential of industrial production, and each reaction can be directly post-fed through simple post-treatment basically.

Synthesis method of (R, S-) nicotine

-

, (2021/05/05)

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (R, S-) nicotine. The method comprises the following steps: (1) taking methyl nicotinate and N-butenyl pyrrolidone as raw materials, and preparing N-butenyl-3-benzoyl-1-pyrrolidone through a condensation reaction; (2) after the reaction is finished, carrying out hydrolysis reaction, cooling, adjusting the pH value to be alkaline, extracting, separating out an organic phase, concentrating and distilling to obtain an enamine intermediate; and (3) carrying out a reduction reaction on the enamine intermediate under illumination with the wavelength of 200-400nm by using a metal oxide or a complex as a reduction catalyst to obtain the target product (R, S-) nicotine. According to the method, use of the metal catalyst is innovatively proposed, reaction is initiated by illumination with specific wavelength to prepare the (R, S-) nicotine, and the method is simple and convenient to operate, high in yield, low in cost and suitable for industrial large-scale production.

Synthesis method of racemic nicotine

-

, (2021/01/04)

The invention discloses a synthesis method of racemic nicotine. The method comprises the following steps: S1, introducing 3-(1-pyrrolin-2-yl) pyridine, a solvent and hydrogen into a first fixed bed reactor filled with a metal catalyst, and cooling at an outlet to obtain a crude product 3-(1-pyrrolidin-2-yl) pyridine mixed solution; and S2, taking the crude product 3-(1-pyrrolidine-2-yl) pyridine and a methylation reagent to pass through a solid second fixed bed reactor filled with a solid base catalyst, and cooling at an outlet to obtain racemic nicotine. The continuous flow fixed bed method is used for preparing racemic nicotine so that the continuity of production is realized, the reaction time is shortened, the reaction operation is simplified, the solvent consumption is reduced, the discharge of waste water and waste liquid is reduced, and the catalyst is convenient to recover.

ENANTIOMERIC SEPARATION OF RACEMIC NICOTINE BY ADDITION OF AN O,O'-DISUBSTITUTED TARTARIC ACID ENANTIOMER

-

, (2019/07/13)

The present invention relates to a method of separating racemic nicotine of Formula (l-a) as a mixture of the (R)- and (S)-enantiomers into the enantiomerically pure (S)- and (R)-nicotine represented by Formula (l-b) and (l-c), by adding a mixture of the L- and the D-enantiomer of a O,O'-disubstituted tartaric acid, wherein the molar ratio of the L- to the D-enantiomer is from 80:20 to 95:5, and obtaining the (S)-nicotine of formula (l-b), or by adding O,O'-dibenzoyl-D-tartaric acid and obtaining the (R)-nicotine of formula (l-c).

PREPARATION OF RACEMIC NICOTINE BY REACTION OF ETHYL NICOTINATE WITH N-VINYLPYRROLIDONE IN THE PRESENCE OF AN ALCOHOLATE BASE AND SUBSEQUENT PROCESS STEPS

-

, (2019/07/13)

The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.

Enantioselective Synthesis of Nicotine via an Iodine-Mediated Hofmann-L?ffler Reaction

Del Castillo, Estefanía,Mu?iz, Kilian

, p. 705 - 708 (2019/02/07)

An iodine-mediated Hofmann-L?ffler reaction has been developed that enables the first enantioselective synthesis of nicotine based on this synthetic methodology. The effect of the free pyridine core on the involved electrophilic iodine reagents was explored in detail. The final synthesis proceeds under moderate reaction conditions that tolerate the free pyridine core. The same synthetic sequence is also applicable to a number of derivatives with higher substituted pyridine cores, including bipyridine derivatives.

Direct α-C-H bond functionalization of unprotected cyclic amines

Chen, Weijie,Ma, Longle,Paul, Anirudra,Seidel, Daniel

, p. 165 - 169 (2018/02/06)

Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp3)–H Amination of Alkyl Azides

Shing, Ka-Pan,Liu, Yungen,Cao, Bei,Chang, Xiao-Yong,You, Tingjie,Che, Chi-Ming

, p. 11947 - 11951 (2018/09/11)

Metal-catalyzed intramolecular C?H amination of alkyl azides constitutes an appealing approach to alicyclic amines; challenges remain in broadening substrate scope, enhancing regioselectivity, and applying the method to natural product synthesis. Herein we report an iron(III) porphyrin bearing axial N-heterocyclic carbene ligands which catalyzes the intramolecular C(sp3)–H amination of a wide variety of alkyl azides under microwave-assisted and thermal conditions, resulting in selective amination of tertiary, benzylic, allylic, secondary, and primary C?H bonds with up to 95 % yield. 14 out of 17 substrates were cyclized selectively at C4 to give pyrrolidines. The regioselectivity at C4 or C5 could be tuned by modifying the reactivity of the C5–H bond. Mechanistic studies revealed a concerted or a fast re-bound mechanism for the amination reaction. The reaction has been applied to the syntheses of tropane, nicotine, cis-octahydroindole, and leelamine derivatives.

Methods of using QIAPINE

-

, (2017/06/30)

Uses of QIAPINE? to treat internal bleeding, such as subdural hematoma and subarachinoid hemorrhage, and ocular bleeding, such as such as hyphema and vitreous hemorrhage, in a subject are described. Also described are uses of QIAPINE? to treat vision loss resulting from hyphema or vitreous hemorrhage.

Design, synthesis and biological evaluation of aminobenzyloxyarylamide derivatives as selective κ opioid receptor antagonists

Wang, Junwei,Song, Qiao,Xu, Anhua,Bao, Yu,Xu, Yungen,Zhu, Qihua

, p. 15 - 25 (2017/03/02)

Opioid receptors play an important role in both behavioral and mood functions. Based on the structural modification of LY2456302, a series of aminobenzyloxyarylamide derivatives were designed and synthesized as κ opioid receptor antagonists. The κ opioid receptor binding ability of these compounds were evaluated with opioid receptors binding assays. Compounds 1a-d showed high affinity for κ opioid receptor. Especially for compound 1c, exhibited a significant Kivalue of 15.7?nM for κ opioid receptor binding and a higher selectivity over μ and δ opioid receptors compared to (±)LY2456302. In addition, compound 1c also showed potent κ antagonist activity with κ IC50?=?9.32?nM in [35S]GTP-γ-S functional assay. The potential use of the representative compounds as antidepressants was also investigated. The most potent compound 1c not only exhibited potent antidepressant activity in the mice forced swimming test, but also displayed the effect of anti-anxiety in the elevated plus-maze test.

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