(4R)-4-Azido-D-Proline hydrochloride
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(4R)-4-Azido-D-Proline hydrochloride

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Category
Azido Amino Acids
Catalog number
BAT-001248
Molecular Formula
C5H9ClN4O2
Molecular Weight
192.60
Synonyms
H-D-Pro(4-N3) HCl (2R,4R); (2R,4R)-4-azidopyrrolidine-2-carboxylic acid hydrochloride
Appearance
White crystalline powder
Purity
≥ 99% (Assay by titration, HPLC)
Melting Point
147-154°C(Dec.)
Storage
Store at 2-8 °C
1. Paroxetine hydrochloride
David Germann, George Ma, Feixue Han, Anna Tikhomirova Profiles Drug Subst Excip Relat Methodol. 2013;38:367-406. doi: 10.1016/B978-0-12-407691-4.00008-3.
Paroxetine hydrochloride (3S-trans)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-piperidine hydrochloride (or (-)-(3S,4R)-(4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)-phenoxy]methyl]piperidine hydrochloride), a phenylpiperidine derivative, is a selective serotonin reuptake inhibitor. Paroxetine is indicated for the treatment of depression, generalized anxiety disorder, obsessive-compulsive disorder, panic disorder, posttraumatic stress disorder, and social anxiety disorder. The physicochemical properties, spectroscopic data (1D and 2D NMR, UV, FT-IR, MS, PXRD), stability, methods of preparation and chromatographic methods of analysis of pharmaceutical, and biological samples of paroxetine are documented in this review. Pharmacokinetics, metabolism, and pharmacological effects are also discussed.
2. Serotonin-1A receptor dependent modulation of pain and reward for improving therapy of chronic pain
Darakhshan Jabeen Haleem Pharmacol Res. 2018 Aug;134:212-219. doi: 10.1016/j.phrs.2018.06.030. Epub 2018 Jun 30.
Chronic pain conditions such as low back pain and osteoarthritis are the most prominent causes of disability worldwide. Morphine and other opioid drugs are the gold standard treatment for severe pain, including surgical pain, but the use of these drugs for chronic pain is limited largely because long term use of these drugs is associated with drug abuse and hyperalgesia which produces a negative impact on the treatment. Non-addictive treatments for chronic pain are, therefore, highly needed. Commonly used opioid drugs activate mu opioid receptors, resulting in an inhibition of tonic activity of nociceptive neurons. The rewarding effects of opioid drugs are also mediated via activation of mu opioid receptors and inhibition of GABA mediated control of the activity of dopamineregic neurons. Enhanced glutamate release and greater activity of NMDA glutamate receptors is linked to the hyperalgesic effects of opioid drugs. Evidence suggests that activation of serotonin (5-hydroxytryptamine; 5-HT)-1 A receptors modulates dopamine neurotransmission to inhibit rewarding effects of drugs of abuse. Activation of these receptors inhibits glutamate release from the sensory neurons to reduce pain transmission. To help develop strategies for improving therapeutics in chronic pain, and draw research interest in the synthesis of non-addictive opioid drugs which do not predispose to hyperalgesia, the present article concerns the potential mechanism involved in 5-HT-1 A receptor mediated inhibition of pain and reward.
3. (3S,4R)-4-(4-Fluoro-phen-yl)-3-(hydroxy-meth-yl)piperidinium chloride
M Nirmala, B R Sreekanth, Peddy Vishweshwar, J Moses Babu, Y Anjaneyulu Acta Crystallogr Sect E Struct Rep Online. 2008 Apr 4;64(Pt 5):o800. doi: 10.1107/S1600536808008593.
The title compound, C(12)H(17)FNO(+)·Cl(-), is a degradation impurity of paroxetine hydro-chloride hemihydrate (PAXIL), an anti-depressant belonging to the group of drugs called selective serotonin reuptake inhibitors (SSRIs). Similar to the paroxetine hydro-chloride salt with protonation having taken place on the basic piperidine ring, the degradation impurity also exists as the hydro-chloride salt. The cyclic six-membered piperidinium ring adopts a chair conformation with the hydroxy-methyl and 4-fluoro-phenyl groups in the equatorial positions. The ions form a tape along the b axis through charge-assisted N(+)-H⋯Cl(-) hydrogen bonds; these tapes are connected by O-H⋯Cl(-) hydrogen bonds along the a axis.
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