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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
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Amines: Introduction01:07

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Internal Receptors01:31

Internal Receptors

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Many cellular signals are hydrophilic and therefore cannot pass through the plasma membrane. However, small or hydrophobic signaling molecules can cross the hydrophobic core of the plasma membrane and bind to internal, or intracellular, receptors that reside within the cell. Many mammalian steroid hormones use this mechanism of cell signaling, as does nitric oxide (NO) gas.
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Trace Amines and Their Receptors.

Raul R Gainetdinov1, Marius C Hoener2, Mark D Berry2

  • 1Institute of Translational Biomedicine, St. Petersburg State University, St. Petersburg, Russia (R.R.G.); Skolkovo Institute of Science and Technology (Skoltech), Moscow, Russia (R.R.G.); Neuroscience, Ophthalmology, and Rare Diseases Discovery and Translational Area, pRED, Roche Innovation Centre Basel, F. Hoffmann-La Roche Ltd., Basel, Switzerland (M.C.H.); and Department of Biochemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, Canada (M.D.B.) gainetdinov.raul@gmail.com.

Pharmacological Reviews
|June 27, 2018
PubMed
Summary

Trace amines and their receptors (TAARs) play crucial roles in both invertebrates and vertebrates. TAAR1 is a key target for treating neurological and metabolic disorders.

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Area of Science:

  • Neuroscience
  • Endocrinology
  • Evolutionary Biology

Background:

  • Trace amines are endogenous compounds found in food and produced by gut microbiota.
  • Distinct trace amine receptor (TAAR) families evolved independently in invertebrates and vertebrates.
  • Invertebrates utilize trace amines for fight-or-flight responses, while vertebrates possess multiple TAAR isoforms.

Purpose of the Study:

  • To provide a comprehensive review of trace amines and their receptors.
  • To explore their evolution, physiological functions, pharmacology, and therapeutic potential.
  • To highlight TAAR1 as a therapeutic target for various diseases.

Main Methods:

  • Literature review of existing research on trace amines and TAARs.
  • Analysis of evolutionary divergence of TAAR families.
  • Examination of TAAR1's roles in central and peripheral systems.

Main Results:

  • Trace amines function differently across species, with high levels in invertebrates and low levels in mammals.
  • Vertebrates express TAARs, with TAAR1 being extensively studied for its roles in neurotransmission and hormone secretion.
  • TAARs in the olfactory epithelium detect environmental cues, while TAAR1 influences neurotransmitter systems and metabolic processes.

Conclusions:

  • Trace amines and TAARs have diverse evolutionary paths and physiological functions.
  • TAAR1 is a promising therapeutic target for neurological disorders (schizophrenia, depression, addiction) and metabolic diseases (diabetes, obesity).
  • Further research into TAARs could unlock new treatment strategies for a range of conditions.