111954-72-4

Basic information

• Product Name: (R)-2-AMINO-5-(3-PYRIDYL)PENTANE
• Synonyms: (R)-2-AMINO-5-(3-PYRIDYL)PENTANE;(R)-5-(3-PYRIDYL)-2-PENTYLAMINE
• CAS NO: 111954-72-4
• Molecular Formula: C₁₀H₁₆N₂
• Molecular Weight: 164.25
• Mol File: 111954-72-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 284.307 °C at 760 mmHg
• Flash Point: 146.383 °C
• Appearance: /
• Density: 0.972 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.519
• PKA: 10.75±0.35(Predicted)
• CAS DataBase Reference: (R)-2-AMINO-5-(3-PYRIDYL)PENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-AMINO-5-(3-PYRIDYL)PENTANE(111954-72-4)
• EPA Substance Registry System: (R)-2-AMINO-5-(3-PYRIDYL)PENTANE(111954-72-4)

Safety Data

• Hazardous Substances Data: 111954-72-4(Hazardous Substances Data)

Usage

General Description

(R)-2-AMINO-5-(3-PYRIDYL)PENTANE, also known as (-)-nicotine, is a naturally occurring alkaloid found in the nightshade family of plants, particularly in tobacco. It is a highly addictive psychoactive substance that acts as a stimulant in the central nervous system. Nicotine is commonly consumed by smoking tobacco products, such as cigarettes, cigars, and pipes, as well as through smokeless tobacco products like chewing tobacco and snuff. It is known for its ability to cause a range of health issues, including addiction, cardiovascular disease, and cancer. Despite its dangers, nicotine has also been used in various therapeutic applications, such as smoking cessation aids and as a potential treatment for certain neurological disorders.

InChI:InChI=1/C10H16N2/c1-9(11)4-2-5-10-6-3-7-12-8-10/h3,6-9H,2,4-5,11H2,1H3/t9-/m1/s1

Upstream product

• 81939-73-3 (2S)-2-hydroxypent-4-yne 
• 152613-93-9 (S)-α-methyl-3-pyridinebutyl butyrate 
• 152533-15-8 (R,S)-α-methyl-3-pyridinebutyl butyrate 
• 152613-92-8 (S)-α-methyl-3-pyridinebutyl acetate 
• 152533-14-7 (R,S)-α-methyl-3-pyridinebutyl acetate 
• 152613-94-0 (S)-α-methyl-3-pyridinebutanol methanesulfonate 
• 142930-52-7 (R,S)-4-hydroxy-1-(3-pyridinyl)-1-pentanone 
• 152613-90-6 (S)-5-(3-pyridinyl)-4-pentyn-2-ol 
• 119981-04-3 alpha-methyl-3-pyridinebutanol 
• 90874-88-7 5-pyridin-3-yl-pentan-2-one 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 111848-81-8 α-methyl-3-pyridinebutanamine 
• 111848-82-9 (R,R)-α-hydroxy-N-<1-methyl-4(3-pyridinyl)butyl>benzeneacetamide 
• 152613-95-1 (R)-3-(4-azidopentyl)pyridine 

Downstream Products

• 120553-55-1 [R,S-(E)]-5,5-bis(3-fluorophenyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide 
• 120553-65-3 [R-(E)]-5,5-bis(4-methoxyphenyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide 
• 120555-28-4 [R-(E,E)]-5-(3-methoxyphenyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2,4-nonadienamide 
• 120555-31-9 Ro 24-0238 
• 120555-35-3 [R-(2E,4Z)]-5-(3-fluorophenyl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2,4-decadienamide 

Relevant articles and documents

SYNTHESIS OF AN ORALLY ACTIVE PAF ANTAGONIST OF THE N-PENTADIENAMIDE CLASS

The PAF antagonist -5-(4-methoxyphenyl)-N--2,4-decadienamide (2) was synthesized from (S)-α-methyl-3-pyridinebutanol (14), which was obtained either from ethyl lactate or by enantioselective kinetic hydrolysis of its racemate using the lipase derived from Pseudomonas cepacia (syn.P. fluorescens).Mesylation of 14, followed by azide displacement and hydrogenation, produced amine (7), which was coupled with the p-nitrophenol ester (8) to give 2.The direct coupling of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid (27) with azide(24) in the presence of tri-n-butylphosphine also gave 2.Acid (27) was prepared by a vinylogous Reformatsky reaction between ketone (25) and methyl 4-bromocrotonate.

Substituted n-[(pyridyl)alkyl]aryl-carboxamide

The invention relates to compounds of the formula STR1 wherein *B is STR2 Y is O or S, *A is *--(CH2)n --(X)m --(CH2)r --, n or r, independently, are integers from 0 to 3, m is an integer from 0 to 1, provided that when m is 1, then n must be at least 1, X is O or S, R1 and R4, independently, are hydrogen, lower alkyl, hydroxy or lower alkoxy, provided that when *B is other than STR3 at least one of R1 and R4, and one of R6 and R7 must be hydrogen, R2 and R3 are independently hydrogen, lower alkyl, cycloalkyl, halogen, nitro, lower alkoxy, lower alkenyl, lower alkynyl or aryl, R5 and R6, independently are hydrogen or lower alkyl, R7 is hydrogen, lower alkyl, cycloalkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R6 and R7 are different, their enantiomers and racemic mixtures thereof, and pharmaceutical acceptable acid addition salts thereof. The compounds of formula I exhibit activity as Platelet Activating Factor (PAF) antagonists and are, therefore, useful as agents for the prevention and treatment of vascular diseases, pulmonary diseases, dermatological disorders, transplant rejection, immunological disorders and inflammatory conditions.

Cyclopropylpropenamides

The invention relates to compounds of the formula STR1 Y is O or S, *A is paraphenylene or *--(CH2)n --(X)m --(CH2)r --, X is O, S or --CH=CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R1 and R2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het or aryl, *E is STR2 or --(CH2)k -- wherein k is an integer from 0 to 4, R3, R4 and R8 are independently hydrogen or lower alkyl, R5 and R6, independently are hydrogen or lower alkyl, R7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and their enantiomers, diastereomers and racemic mixtures thereof, as well as when *E is STR3 their geometric isomers, and pharmaceutically acceptable acid addition salts thereof. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characterized by excess platelet activating factor or for the prevention and treatment of cardiovascular diseases, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.