136329-39-0

Basic information

• Product Name: (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE
• Synonyms: (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE;(R)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE;(R)-1-(METHYLAMINO)-1-PHENYL-2-(1-PYRROLIDINYL)ETHANE;(1-PHENYL-2-PYRROLIDINYLETHYL)METHYLAMINE;METHYL-(1-PHENYL-2-PYRROLIDIN-1-YL-ETHYL)-AMINE;(R)-(-)-N-Methyl-1-phenyl-2-(1-pyrrolidine)ethylamine;(R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE: TECH., 90%;(R)-(-)-N-Methyl-1-phenyl-2-(1-pyrrolidinyl)ethylamine, tech. 90%
• CAS NO: 136329-39-0
• Molecular Formula: C₁₃H₂₀N₂
• Molecular Weight: 204.31
• EINECS: -0
• Mol File: 136329-39-0.mol

Chemical Properties

• Boiling Point: 296.1 °C at 760 mmHg
• Flash Point: 113.1 °C
• Appearance: /
• Density: 0,974 g/cm3
• Vapor Pressure: 0.00146mmHg at 25°C
• Refractive Index: 1.5245
• Storage Temp.: 2-8°C
• PKA: 9.88±0.20(Predicted)
• Sensitive: Air Sensitive
• BRN: 4842022
• CAS DataBase Reference: (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE(136329-39-0)
• EPA Substance Registry System: (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE(136329-39-0)

Safety Data

• Statements: 34-52
• Safety Statements: 26-36/37/39-45
• RIDADR: 2735
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 136329-39-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE is used as a reference compound in pharmaceutical research for studying the effects and mechanisms of action of psychoactive substances. Its potent activity, particularly in the (R)-(-) enantiomer, provides valuable insights into the development of new drugs targeting the central nervous system.
Used in Neurochemical Studies:
In the field of neurochemistry, (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE serves as a tool to investigate the role of neurotransmitters such as dopamine and norepinephrine. Its ability to increase the release of these neurotransmitters helps researchers understand their functions in the brain and their involvement in various neurological and psychiatric disorders.
Used in Drug Development:
(R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE is utilized in the development of new drugs aimed at treating conditions related to the central nervous system. Its enantiomeric forms offer a unique opportunity to explore the differences in their pharmacological effects, potentially leading to the creation of more effective and safer medications.
Used in Toxicological Studies:
In toxicology, (R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE is employed to study the toxic effects of psychoactive substances on the body. Understanding its impact on the central nervous system can help in the assessment of risks associated with the use of similar compounds.
Used in Forensic Analysis:
(R)-(-)-N-METHYL-1-PHENYL-2-(1-PYRROLIDINO)ETHYLAMINE is also used in forensic analysis to identify and differentiate between enantiomers of psychoactive drugs. This capability is crucial in cases involving drug-related crimes, as it can provide evidence of the specific substance involved.

InChI:InChI=1/C13H20N2/c1-14-13(11-15-9-5-6-10-15)12-7-3-2-4-8-12/h2-4,7-8,13-14H,5-6,9-11H2,1H3

Upstream product

• 123-75-1 pyrrolidine 
• 20780-53-4 (R)-Styrene oxide 
• 74-89-5 methylamine 
• 10419-72-4 (S)-(+)-2-(N-formylamino)-2-phenylacetic acid 
• 17609-52-8 Z-D-phenylglycine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 180305-84-4 (S)-2-(Pyrrolidin-1-yl)-2-phenylethanol 
• 136329-29-8 (R)-1-pyrrolidine 

Downstream Products

• 136328-89-7 (R)-2-(3,4-dichlorophenyl)-N-methyl-N-[1-phenyl-2-(pyrrolidin-1-yl)ethyl]acetamide 

Relevant articles and documents

A simple and efficient method for the preparation of homochiral amines: Application to the synthesis of a new C2 symmetric triamine

Using a one-pot reaction, (R)-styrene oxide has been converted into a variety of novel diamines and a C2 symmetric triamine. Yields range from 63-93%. The method is simple, efficient and is considerably shorter than other synthetic approaches.

Two expedient methods for the preparation of chiral diamines

A study on the development of methodology for the synthesis of chiral diamines is reported. Two synthetic approaches are described both of which involve the generation and subsequent reaction of aziridinium ions. One of the methods is a one-pot preparatio

Two useful methods for the preparation of (R)- and (S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)ethanamine

Two methods for the efficient preparation of either enantiomer of the synthetically useful diamine N-methyl-1-phenyl-2-(1-pyrrolidinyl)ethanamine are reported. Each of the methods starts from readily available materials (styrene oxide or phenylglycinol) a

Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides

The reaction of epoxides with chiral nonracemic lithium amide bases, designed and prepared from (R)-phenylglycine, has been studied in detail. A maximum of 80% ee was obtained for conversion of cyclohexene oxide to (S)-2-cyclohexen-1-ol. Enantioselective deprotonation of a variety of other epoxides was studied. A cyclopentanoid core unit for prostaglandin synthesis was synthesized in 97% ee.

Synthesis of Versatile Intermediates for Cyclopentanoid Natural Products via Enantioselective Deprotonation of Substituted Cyclopentene Oxide

Enantioselective deprotonation of cis and trans-3,4-epoxycyclopentan-1-ol derivatives with phenylglycine based ligand (R)-5 was studied.The cyclopentanoid intermediates were obtained in a maximum of 88percent ee.

Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, part IV. Relationship between ligand structure and enantioselectivity

Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Nonlinear asymmetric induction was observed with the cuprate formed from ligand 13.

Structure/Activity Studies Related to 2-(3,4-Dichlorophenyl)-N-methyl-N-acetamides: A Novel Series of Potent and Selective κ-Opioid Agonists

This paper describes the synthesis of a series of N-acetamides 1, variously substituted at the carbon adjacent to the amide nitrogen (C1), and related analogues, together with their biological evaluation as opioid κ agonists.In the first part of the study, the variants in N-acyl, N-alkyl, and amino functions were explored when the substituent at C1 was 1-methylethyl and the optimum was found to be exemplified by 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (13).Subsequently, racemic or chiral amino acids were used to introduce other alkyl and aryl substituents at C1 of the ethyl linking moiety.A series of potent compounds, bearing substituted-aryl groups at C1, were discovered, typified by 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (48), which was 5-fold more active as the racemate than 13 in vitro and exhibited potent naloxone-reversible analgesic effects (ED50 = 0.04 mg/kg sc) in a mouse abdominal constriction model.