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Related Concept Videos

Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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SN2 Reaction: Stereochemistry02:23

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Isomerism in Alkenes02:01

Isomerism in Alkenes

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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Naming Enantiomers02:21

Naming Enantiomers

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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Updated: Mar 8, 2026

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA
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Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA

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Mistaking 2C-P for 2C-B: What a Difference a Letter Makes.

Adrian Stoller1, Patrick C Dolder2,3, Michael Bodmer4

  • 1Department of Nephrology, Hypertension and Clinical Pharmacology, Inselspital, Bern University Hospital, University of Bern, Switzerland.

Journal of Analytical Toxicology
|January 29, 2017
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Summary

A man experienced severe symptoms after taking a substance sold as 2C-B. Analysis revealed it was the more potent 2C-P, highlighting differences in 2C drug potency and effects.

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Area of Science:

  • Pharmacology
  • Toxicology
  • Forensic Chemistry

Background:

  • The 2C drug family, including 2,5-dimethoxy-4(n)-propylphenethylamine (2C-P) and 2,5-dimethoxy-4-bromophenethylamine (2C-B), are synthetic phenethylamines known for psychoactive properties.
  • Variations in the 4-position ligand significantly alter receptor affinity, potency, and duration of action among 2C compounds.

Observation:

  • A 19-year-old male presented with severe hallucinations, mydriasis, tachycardia, agitation, and confusion after ingesting a substance misrepresented as 2C-B.
  • Liquid chromatography-mass spectrometry analysis confirmed the presence of the more potent 2C-P in the patient's blood samples.

Findings:

  • The estimated elimination half-life of 2C-P, based on two blood samples, was determined to be 19 hours.
  • This case demonstrates a critical distinction in potency between 2C-B and 2C-P, with 2C-P exhibiting significantly stronger effects.

Implications:

  • This case underscores the importance of accurate substance identification in emergency toxicology, especially with novel psychoactive substances.
  • Understanding the pharmacokinetic and pharmacodynamic differences between related 2C drugs is crucial for clinical management and public health awareness regarding designer drugs.